2,2′-Bis(1-ethyl­benzimidazol-2-yl)­bi­phenyl

Stibrany, R.T.; Schugar, H.J.; Potenza, J.A.

doi:10.1107/S1600536803007852

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2,2′-Bis(1-ethylbenzimidazol-2-yl)biphenyl

R. T. Stibrany, H. J. Schugar and J. A. Potenza

The title compound, C₃₀H₂₆N₄, adopts a folded, twisted clamshell geometry in the solid state in which the ethyl groups are trans, and in which the imidazole fragments of the benzimidazole units are nearly eclipsed. Distances between imidazole fragments indicate extensive intramolecular π–π interactions. The molecules pack in columns along b with little, if any, intermolecular π–π interactions. In contrast, the n-propyl analog, 2,2′-bis(1-propylbenzimidazol-2-yl)]biphenyl, adopts an extended conformation with little, if any, π–π interactions of any kind.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007852/ac6037sup1.cif Contains datablocks IIa, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007852/ac6037IIasup2.hkl Contains datablock IIa

CCDC reference: 214630

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.060
wR factor = 0.174
Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.869     1.000
          Tmin' and Tmax expected:      0.972     0.981
          RR' =      0.877
          Please check that your absorption correction is appropriate.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Bis(imidazole)biphenyl and bis(benzimidazole)biphenyl species such as (I) and (II), with three torsional degrees of freedom, have been used as ligands to study electron self-exchange (Knapp et al., 1990; Xie et al., 1999) and to enforce near-tetrahedral coordination in transition metal complexes (Stibrany et al., 2003). They have also found use in catalysis (Stibrany, Matturo et al., 2002) and have been shown to act as proton sponges (Stibrany, Schugar & Potenza, 2002).

The title compound, (IIa) (Fig. 1) adopts a compact twisted clamshell conformation with the ethyl groups trans. Both the phenyl (ph) and benzimidazole (bz) fragments are planar. Fragment planarity, coupled with the ph/ph [63.10 (8)°] and ph/bz [54.47 (6) and 48.29 (6)°] dihedral angles, give the molecule a pseudo twofold axis passing through the midpoint of the C21—C31 bond and between the bz fragments. The shortest distances between C and N atoms of the nearly-eclipsed imidazole fragments range from 3.167 (3) Å for C12···C42 to 3.673 (3) Å for N11···C43, indicative of intramolecular π–π interactions. In type (II) species, the molecular shape correlates with the ph/ph dihedral angle. Thus, the proton sponge IIbH⁺ (Stibrany, Schugar & Potenza, 2002) adopts a more open structure than (IIa), consistent with its larger ph/ph dihedral angle [88.6 (6)°], while molecules of (IIb), with ph/ph dihedral angles of 126.71 (1) and 129.93 (1)° for two unique molecules, exhibit an open trans structure with little evidence of intra or intermolecular π–π interactions (Stibrany et al., 2003).

Metric parameters in the benzimidazole fragments of (IIa) agree well with those reported for 18 neutral benzimidazole structures (III) having carbon substituents at the N1 and C2 positions (Cambridge Structural Database, Version 5.24, Allen 2003; refcodes: DIKFEI, HIXXAX, HOHHUH, JELROH, LEBGOO, MEVTAI, MEVTEM, NUBCOC, QAXKAB, QIBPEW, QIFPOK, SAGDIN, UBIPUQ, XITZOP, YAXDAC and ZENSOA). Benzimidazoles unsubstituted at the C2 position, IV, show equivalent distances for the imidazole fragments except for the the C2—N(amine) distances which are significantly shorter in the unsubstituted compounds (Allen, 2003; refcodes: CAXKUH, MIFVUS, NEBFUV, SEMWAI, SIGVIG and VENSAI). We have not explored the extent to which this difference arises from steric and/or electronic effects.

Molecules of (IIa) stack along b in columns (Fig. 2) related to each other by the centers of symmetry, glide planes and screw axes of the space group.

Experimental top

The title compound, (IIa), was obtained by condensation of phenylenediamine with diphenic acid, followed by alkylation with ethyl iodide. Details of the preparation will be published elsewhere (Stibrany et al., 2003). Crystals were obtained by slow evaporation of a solution of (IIa) in a mixture of ethanol and triethyl orthoformate. ¹H NMR (400 MHz, CDCl₃): δ 7.60 (d, J = 7.0 Hz, 2H), 7.41 (d, J = 6.5 Hz, 2H), 7.30 (m, 6H), 7.23 (m, 6H), 3.67 (brd s, 4H), 1.19 (t, J = 7.0 Hz, 6H). ¹³C NMR (400 MHz, CDCl₃): δ 152.5 143.4, 141.1, 134.5, 131.5, 130.7, 130.0, 129.4, 127.41, 122.2, 121.8, 120.0, 110.0, 38.9, 14.8.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

	Fig. 1. The molecular structure of the title compound showing 25% probability displacement ellipsiods.
	Fig. 2. View of the unit-cell along b. H atoms have been omitted for clarity.

2,2'-bis(1-ethylbenzimidazol-2-yl)biphenyl top

Crystal data top

C₃₀H₂₆N₄	D_x = 1.232 Mg m⁻³ D_m = 1.19 (1) Mg m⁻³ D_m measured by floatation-carbontetrachloride/cyclohexane
M_r = 442.55	Melting point: 160 °C soften, 176 °C melt K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.0156 (6) Å	Cell parameters from 821 reflections
b = 10.7001 (6) Å	θ = 2.2–23.1°
c = 18.6280 (9) Å	µ = 0.07 mm⁻¹
β = 95.177 (4)°	T = 294 K
V = 2385.2 (2) Å³	Block, colorless
Z = 4	0.38 × 0.36 × 0.26 mm
F(000) = 936

Data collection top

Bruker SMART CCD area-detector diffractometer	4179 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −13→14
T_min = 0.869, T_max = 1.000	k = −12→12
16281 measured reflections	l = −22→22

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	All H-atom parameters refined
S = 1.00	w = 1/[σ²(F_o²) + (0.1086P)² + 0.4514P] where P = (F_o² + 2F_c²)/3
4179 reflections	(Δ/σ)_max < 0.001
411 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₃₀H₂₆N₄	V = 2385.2 (2) Å³
M_r = 442.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0156 (6) Å	µ = 0.07 mm⁻¹
b = 10.7001 (6) Å	T = 294 K
c = 18.6280 (9) Å	0.38 × 0.36 × 0.26 mm
β = 95.177 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4179 independent reflections
Absorption correction: multi-scan (SADABS; Blessing, 1995)	3375 reflections with I > 2σ(I)
T_min = 0.869, T_max = 1.000	R_int = 0.036
16281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.174	All H-atom parameters refined
S = 1.00	Δρ_max = 0.16 e Å⁻³
4179 reflections	Δρ_min = −0.13 e Å⁻³
411 parameters

Special details top

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
N41	0.59103 (14)	0.81751 (16)	0.05983 (9)	0.0427 (5)
N43	0.59743 (14)	0.95822 (17)	0.15012 (10)	0.0458 (5)
C31	0.81740 (17)	1.04253 (18)	0.08511 (12)	0.0407 (5)
N13	0.89082 (14)	0.77034 (16)	0.09423 (10)	0.0455 (5)
C43	0.52664 (17)	0.8610 (2)	0.16486 (12)	0.0468 (6)
N11	0.79324 (15)	0.69086 (17)	0.18087 (10)	0.0486 (5)
C42	0.63436 (15)	0.92883 (19)	0.08813 (11)	0.0380 (5)
C33	0.68646 (19)	1.0394 (2)	−0.02063 (12)	0.0459 (5)
C36	0.8909 (2)	1.1063 (2)	0.04448 (15)	0.0521 (6)
C21	0.85132 (16)	1.0249 (2)	0.16386 (12)	0.0438 (5)
C32	0.71418 (16)	1.00419 (18)	0.05033 (11)	0.0381 (5)
C13	0.85651 (17)	0.6501 (2)	0.07525 (13)	0.0455 (6)
C11	0.79570 (17)	0.5991 (2)	0.12848 (13)	0.0490 (6)
C35	0.8633 (2)	1.1361 (2)	−0.02681 (14)	0.0557 (7)
C14	0.8730 (2)	0.5817 (2)	0.01363 (16)	0.0593 (7)
C34	0.7595 (2)	1.1063 (2)	−0.05890 (14)	0.0514 (6)
C22	0.86932 (17)	0.9084 (2)	0.19764 (12)	0.0466 (6)
C12	0.85190 (16)	0.7914 (2)	0.15681 (12)	0.0431 (5)
C23	0.9077 (2)	0.9049 (3)	0.27054 (14)	0.0616 (7)
C48	0.61912 (19)	0.7499 (2)	−0.00434 (13)	0.0490 (6)
C47	0.4603 (2)	0.6622 (3)	0.11279 (17)	0.0604 (7)
C44	0.4674 (2)	0.8414 (3)	0.22533 (15)	0.0605 (7)
C17	0.7480 (2)	0.4805 (2)	0.12222 (18)	0.0647 (8)
C26	0.8700 (2)	1.1325 (3)	0.20533 (15)	0.0572 (7)
C41	0.52231 (16)	0.7726 (2)	0.10981 (12)	0.0461 (6)
C18	0.7329 (2)	0.6805 (3)	0.24523 (15)	0.0630 (7)
C49	0.5278 (3)	0.7518 (3)	−0.06608 (18)	0.0713 (8)
C24	0.9255 (2)	1.0128 (3)	0.31014 (16)	0.0719 (8)
C25	0.9061 (2)	1.1258 (3)	0.27797 (16)	0.0684 (8)
C45	0.4077 (2)	0.7330 (3)	0.22822 (19)	0.0747 (9)
C19	0.7921 (4)	0.5953 (5)	0.3016 (2)	0.0993 (13)
C46	0.4042 (2)	0.6450 (3)	0.1730 (2)	0.0755 (9)
C15	0.8263 (2)	0.4640 (3)	0.0073 (2)	0.0721 (8)
C16	0.7656 (2)	0.4149 (3)	0.06084 (19)	0.0736 (9)
H14	0.910 (2)	0.619 (2)	−0.0257 (16)	0.076 (9)*
H47	0.4615 (19)	0.604 (2)	0.0752 (12)	0.047 (7)*
H17	0.706 (2)	0.451 (2)	0.1592 (14)	0.067 (8)*
H46	0.363 (3)	0.567 (3)	0.1754 (16)	0.088 (9)*
H45	0.368 (2)	0.720 (3)	0.2701 (17)	0.083 (9)*
H16	0.733 (3)	0.331 (3)	0.0559 (17)	0.095 (10)*
H44	0.469 (3)	0.904 (3)	0.2635 (16)	0.086 (10)*
H33	0.612 (2)	1.018 (2)	−0.0432 (11)	0.049 (6)*
H36	0.963 (2)	1.129 (2)	0.0680 (12)	0.051 (6)*
H35	0.915 (2)	1.176 (2)	−0.0535 (13)	0.054 (7)*
H25	0.916 (2)	1.201 (2)	0.3040 (14)	0.062 (7)*
H26	0.857 (2)	1.215 (3)	0.1821 (13)	0.066 (8)*
H34	0.739 (2)	1.127 (2)	−0.1072 (15)	0.061 (7)*
H23	0.921 (2)	0.828 (3)	0.2966 (14)	0.069 (8)*
H15	0.836 (2)	0.415 (3)	−0.0347 (17)	0.084 (9)*
H24	0.957 (3)	1.009 (3)	0.3606 (17)	0.083 (9)*
H48A	0.634 (2)	0.661 (2)	0.0106 (13)	0.060 (7)*
H48B	0.690 (2)	0.787 (2)	−0.0191 (12)	0.055 (6)*
H18B	0.656 (2)	0.643 (2)	0.2283 (14)	0.071 (8)*
H18A	0.727 (2)	0.769 (3)	0.2645 (14)	0.073 (8)*
H49C	0.549 (3)	0.697 (3)	−0.104 (2)	0.110 (12)*
H49B	0.514 (2)	0.840 (3)	−0.0850 (15)	0.083 (9)*
H49A	0.458 (3)	0.719 (3)	−0.0468 (17)	0.095 (10)*
H19A	0.750 (3)	0.598 (4)	0.343 (2)	0.119 (13)*
H19B	0.865 (4)	0.628 (4)	0.319 (2)	0.137 (17)*
H19C	0.800 (4)	0.505 (5)	0.279 (3)	0.17 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N41	0.0387 (9)	0.0450 (10)	0.0438 (11)	−0.0024 (8)	−0.0005 (8)	0.0022 (8)
N43	0.0386 (10)	0.0537 (11)	0.0451 (12)	−0.0019 (8)	0.0033 (8)	0.0023 (9)
C31	0.0422 (11)	0.0339 (11)	0.0459 (13)	−0.0011 (9)	0.0036 (9)	−0.0029 (9)
N13	0.0386 (10)	0.0460 (10)	0.0518 (12)	0.0014 (8)	0.0035 (8)	0.0077 (9)
C43	0.0359 (11)	0.0570 (14)	0.0469 (14)	0.0024 (10)	0.0010 (10)	0.0104 (11)
N11	0.0437 (10)	0.0527 (11)	0.0498 (12)	0.0002 (8)	0.0058 (8)	0.0146 (9)
C42	0.0322 (10)	0.0432 (11)	0.0376 (12)	0.0009 (8)	−0.0022 (9)	0.0024 (9)
C33	0.0472 (13)	0.0468 (12)	0.0435 (14)	0.0016 (10)	0.0029 (10)	−0.0002 (10)
C36	0.0467 (14)	0.0459 (13)	0.0644 (17)	−0.0085 (10)	0.0094 (12)	0.0010 (11)
C21	0.0325 (11)	0.0521 (13)	0.0465 (13)	−0.0058 (9)	0.0014 (9)	−0.0032 (10)
C32	0.0386 (11)	0.0378 (10)	0.0379 (12)	0.0017 (8)	0.0030 (9)	−0.0001 (9)
C13	0.0356 (11)	0.0433 (12)	0.0568 (15)	0.0038 (9)	0.0006 (10)	0.0097 (11)
C11	0.0381 (12)	0.0455 (12)	0.0629 (16)	0.0049 (9)	0.0022 (11)	0.0095 (11)
C35	0.0683 (17)	0.0436 (13)	0.0585 (17)	−0.0058 (11)	0.0245 (14)	0.0059 (12)
C14	0.0523 (14)	0.0562 (15)	0.0704 (19)	0.0078 (11)	0.0113 (13)	0.0002 (14)
C34	0.0679 (16)	0.0467 (13)	0.0408 (14)	0.0031 (11)	0.0111 (12)	0.0032 (11)
C22	0.0366 (11)	0.0568 (14)	0.0459 (14)	−0.0048 (9)	0.0012 (10)	0.0043 (11)
C12	0.0344 (11)	0.0497 (13)	0.0445 (13)	0.0018 (9)	−0.0010 (9)	0.0105 (10)
C23	0.0512 (14)	0.0815 (19)	0.0501 (16)	−0.0055 (13)	−0.0069 (12)	0.0088 (14)
C48	0.0469 (13)	0.0484 (14)	0.0507 (15)	0.0008 (10)	−0.0009 (11)	−0.0027 (11)
C47	0.0498 (14)	0.0566 (15)	0.0737 (19)	−0.0064 (11)	0.0003 (13)	0.0112 (15)
C44	0.0447 (13)	0.0817 (19)	0.0560 (17)	0.0018 (12)	0.0100 (12)	0.0120 (15)
C17	0.0530 (15)	0.0513 (15)	0.091 (2)	−0.0020 (11)	0.0138 (15)	0.0156 (15)
C26	0.0483 (13)	0.0596 (16)	0.0630 (18)	−0.0103 (11)	0.0016 (12)	−0.0123 (13)
C41	0.0359 (11)	0.0512 (13)	0.0504 (14)	−0.0019 (9)	−0.0013 (10)	0.0122 (11)
C18	0.0561 (16)	0.0757 (19)	0.0580 (17)	−0.0034 (13)	0.0101 (13)	0.0180 (14)
C49	0.074 (2)	0.074 (2)	0.063 (2)	−0.0008 (16)	−0.0119 (16)	−0.0115 (16)
C24	0.0623 (17)	0.104 (2)	0.0480 (17)	−0.0217 (15)	−0.0052 (13)	−0.0047 (17)
C25	0.0573 (15)	0.086 (2)	0.0614 (19)	−0.0225 (14)	0.0016 (13)	−0.0274 (17)
C45	0.0512 (15)	0.102 (2)	0.072 (2)	−0.0045 (15)	0.0155 (14)	0.0303 (19)
C19	0.105 (3)	0.121 (3)	0.073 (3)	0.002 (3)	0.014 (2)	0.052 (2)
C46	0.0516 (15)	0.0725 (19)	0.102 (3)	−0.0145 (14)	0.0044 (16)	0.0370 (19)
C15	0.0631 (17)	0.0559 (16)	0.099 (2)	0.0033 (13)	0.0156 (16)	−0.0131 (17)
C16	0.0624 (17)	0.0450 (15)	0.114 (3)	0.0002 (13)	0.0128 (17)	−0.0053 (16)

Geometric parameters (Å, º) top

N11—C12	1.383 (3)	C23—C24	1.377 (4)
N41—C42	1.385 (3)	C23—H23	0.96 (3)
N13—C12	1.314 (3)	C48—C49	1.516 (4)
N43—C42	1.312 (3)	C48—H48A	1.00 (3)
N13—C13	1.387 (3)	C48—H48B	1.00 (2)
N43—C43	1.387 (3)	C47—C46	1.372 (4)
N11—C11	1.387 (3)	C47—C41	1.401 (3)
N41—C41	1.385 (3)	C47—H47	0.94 (2)
C11—C13	1.395 (3)	C44—C45	1.368 (4)
C41—C43	1.393 (3)	C44—H44	0.98 (3)
N41—C48	1.463 (3)	C17—C16	1.374 (4)
C31—C36	1.393 (3)	C17—H17	0.95 (3)
C31—C32	1.408 (3)	C26—C25	1.385 (4)
C31—C21	1.499 (3)	C26—H26	0.99 (3)
C43—C44	1.401 (3)	C18—C19	1.518 (4)
N11—C18	1.460 (3)	C18—H18B	1.03 (3)
C42—C32	1.479 (3)	C18—H18A	1.02 (3)
C33—C34	1.379 (3)	C49—H49C	0.98 (4)
C33—C32	1.386 (3)	C49—H49B	1.01 (3)
C33—H33	0.99 (2)	C49—H49A	1.00 (3)
C36—C35	1.377 (4)	C24—C25	1.360 (4)
C36—H36	0.97 (2)	C24—H24	0.98 (3)
C21—C26	1.393 (3)	C25—H25	0.94 (3)
C21—C22	1.403 (3)	C45—C46	1.392 (5)
C13—C14	1.390 (4)	C45—H45	0.96 (3)
C11—C17	1.393 (3)	C19—H19A	0.96 (4)
C35—C34	1.372 (4)	C19—H19B	0.97 (5)
C35—H35	0.93 (2)	C19—H19C	1.06 (5)
C14—C15	1.379 (4)	C46—H46	0.97 (3)
C14—H14	0.98 (3)	C15—C16	1.390 (4)
C34—H34	0.94 (3)	C15—H15	0.95 (3)
C22—C23	1.395 (3)	C16—H16	0.98 (3)
C22—C12	1.470 (3)

C42—N41—C41	105.60 (17)	C49—C48—H48A	108.6 (14)
C42—N41—C48	129.06 (18)	N41—C48—H48B	107.1 (13)
C41—N41—C48	124.96 (18)	C49—C48—H48B	111.3 (13)
C42—N43—C43	104.87 (18)	H48A—C48—H48B	108.7 (19)
C36—C31—C32	117.9 (2)	C46—C47—C41	116.6 (3)
C36—C31—C21	117.64 (19)	C46—C47—H47	124.3 (14)
C32—C31—C21	124.35 (18)	C41—C47—H47	119.1 (14)
C12—N13—C13	105.30 (18)	C45—C44—C43	117.7 (3)
N43—C43—C41	110.28 (19)	C45—C44—H44	122.2 (18)
N43—C43—C44	129.5 (2)	C43—C44—H44	120.1 (18)
C41—C43—C44	120.1 (2)	C16—C17—C11	116.2 (3)
C12—N11—C11	106.21 (18)	C16—C17—H17	124.7 (16)
C12—N11—C18	129.1 (2)	C11—C17—H17	119.0 (16)
C11—N11—C18	124.6 (2)	C25—C26—C21	121.3 (3)
N43—C42—N41	113.32 (18)	C25—C26—H26	119.8 (15)
N43—C42—C32	125.01 (18)	C21—C26—H26	118.9 (15)
N41—C42—C32	121.68 (18)	N41—C41—C43	105.92 (18)
C34—C33—C32	121.7 (2)	N41—C41—C47	132.1 (2)
C34—C33—H33	120.0 (13)	C43—C41—C47	121.9 (2)
C32—C33—H33	118.3 (13)	N11—C18—C19	112.1 (3)
C35—C36—C31	121.9 (2)	N11—C18—H18B	106.0 (15)
C35—C36—H36	120.4 (13)	C19—C18—H18B	109.3 (15)
C31—C36—H36	117.7 (13)	N11—C18—H18A	106.0 (15)
C26—C21—C22	118.3 (2)	C19—C18—H18A	111.1 (15)
C26—C21—C31	117.0 (2)	H18B—C18—H18A	112 (2)
C22—C21—C31	124.62 (19)	C48—C49—H49C	109 (2)
C33—C32—C31	119.0 (2)	C48—C49—H49B	111.3 (17)
C33—C32—C42	119.48 (19)	H49C—C49—H49B	111 (3)
C31—C32—C42	121.46 (19)	C48—C49—H49A	107.0 (19)
N13—C13—C14	129.6 (2)	H49C—C49—H49A	109 (3)
N13—C13—C11	110.1 (2)	H49B—C49—H49A	109 (3)
C14—C13—C11	120.3 (2)	C25—C24—C23	119.8 (3)
N11—C11—C17	132.0 (2)	C25—C24—H24	119.4 (17)
N11—C11—C13	105.62 (19)	C23—C24—H24	120.7 (17)
C17—C11—C13	122.3 (2)	C24—C25—C26	120.2 (3)
C34—C35—C36	119.8 (2)	C24—C25—H25	121.4 (16)
C34—C35—H35	120.0 (14)	C26—C25—H25	118.4 (16)
C36—C35—H35	120.2 (14)	C44—C45—C46	121.7 (3)
C15—C14—C13	117.6 (3)	C44—C45—H45	117.2 (18)
C15—C14—H14	121.2 (16)	C46—C45—H45	121.1 (18)
C13—C14—H14	120.9 (16)	C18—C19—H19A	107 (2)
C35—C34—C33	119.4 (2)	C18—C19—H19B	111 (3)
C35—C34—H34	120.9 (16)	H19A—C19—H19B	105 (3)
C33—C34—H34	119.7 (16)	C18—C19—H19C	109 (3)
C23—C22—C21	119.0 (2)	H19A—C19—H19C	114 (4)
C23—C22—C12	120.0 (2)	H19B—C19—H19C	111 (4)
C21—C22—C12	121.0 (2)	C47—C46—C45	121.9 (3)
N13—C12—N11	112.7 (2)	C47—C46—H46	116.2 (18)
N13—C12—C22	124.04 (19)	C45—C46—H46	121.9 (18)
N11—C12—C22	123.2 (2)	C14—C15—C16	121.3 (3)
C24—C23—C22	121.4 (3)	C14—C15—H15	119.4 (18)
C24—C23—H23	116.0 (16)	C16—C15—H15	119.3 (18)
C22—C23—H23	122.6 (16)	C17—C16—C15	122.2 (3)
N41—C48—C49	114.1 (2)	C17—C16—H16	117.1 (19)
N41—C48—H48A	106.8 (14)	C15—C16—H16	120.7 (19)

C42—N43—C43—C41	0.0 (2)	C31—C21—C22—C12	−2.1 (3)
C42—N43—C43—C44	177.4 (2)	C13—N13—C12—N11	0.1 (2)
C43—N43—C42—N41	0.8 (2)	C13—N13—C12—C22	179.55 (18)
C43—N43—C42—C32	−179.26 (18)	C11—N11—C12—N13	−0.1 (2)
C41—N41—C42—N43	−1.2 (2)	C18—N11—C12—N13	−176.3 (2)
C48—N41—C42—N43	−174.41 (19)	C11—N11—C12—C22	−179.56 (19)
C41—N41—C42—C32	178.81 (17)	C18—N11—C12—C22	4.2 (3)
C48—N41—C42—C32	5.6 (3)	C23—C22—C12—N13	−130.5 (2)
C32—C31—C36—C35	2.5 (3)	C21—C22—C12—N13	47.4 (3)
C21—C31—C36—C35	−174.6 (2)	C23—C22—C12—N11	48.8 (3)
C36—C31—C21—C26	60.1 (3)	C21—C22—C12—N11	−133.2 (2)
C32—C31—C21—C26	−116.7 (2)	C21—C22—C23—C24	1.6 (4)
C36—C31—C21—C22	−117.4 (2)	C12—C22—C23—C24	179.6 (2)
C32—C31—C21—C22	65.7 (3)	C42—N41—C48—C49	−109.9 (3)
C34—C33—C32—C31	2.9 (3)	C41—N41—C48—C49	78.1 (3)
C34—C33—C32—C42	−177.9 (2)	N43—C43—C44—C45	−176.4 (2)
C36—C31—C32—C33	−4.9 (3)	C41—C43—C44—C45	0.9 (3)
C21—C31—C32—C33	171.94 (19)	N11—C11—C17—C16	178.3 (2)
C36—C31—C32—C42	175.93 (19)	C13—C11—C17—C16	1.0 (4)
C21—C31—C32—C42	−7.2 (3)	C22—C21—C26—C25	0.4 (3)
N43—C42—C32—C33	−126.1 (2)	C31—C21—C26—C25	−177.3 (2)
N41—C42—C32—C33	53.8 (3)	C42—N41—C41—C43	1.1 (2)
N43—C42—C32—C31	53.0 (3)	C48—N41—C41—C43	174.65 (18)
N41—C42—C32—C31	−127.0 (2)	C42—N41—C41—C47	−176.7 (2)
C12—N13—C13—C14	178.7 (2)	C48—N41—C41—C47	−3.1 (4)
C12—N13—C13—C11	−0.1 (2)	N43—C43—C41—N41	−0.7 (2)
C12—N11—C11—C17	−177.5 (2)	C44—C43—C41—N41	−178.43 (19)
C18—N11—C11—C17	−1.1 (4)	N43—C43—C41—C47	177.3 (2)
C12—N11—C11—C13	0.1 (2)	C44—C43—C41—C47	−0.4 (3)
C18—N11—C11—C13	176.5 (2)	C46—C47—C41—N41	177.1 (2)
N13—C13—C11—N11	0.0 (2)	C46—C47—C41—C43	−0.3 (3)
C14—C13—C11—N11	−178.87 (19)	C12—N11—C18—C19	−108.9 (4)
N13—C13—C11—C17	177.9 (2)	C11—N11—C18—C19	75.5 (4)
C14—C13—C11—C17	−1.0 (3)	C22—C23—C24—C25	−0.3 (4)
C31—C36—C35—C34	2.1 (4)	C23—C24—C25—C26	−0.9 (4)
N13—C13—C14—C15	−178.0 (2)	C21—C26—C25—C24	0.9 (4)
C11—C13—C14—C15	0.7 (4)	C43—C44—C45—C46	−0.6 (4)
C36—C35—C34—C33	−4.2 (4)	C41—C47—C46—C45	0.6 (4)
C32—C33—C34—C35	1.7 (3)	C44—C45—C46—C47	−0.1 (4)
C26—C21—C22—C23	−1.6 (3)	C13—C14—C15—C16	−0.5 (4)
C31—C21—C22—C23	175.9 (2)	C11—C17—C16—C15	−0.8 (4)
C26—C21—C22—C12	−179.55 (19)	C14—C15—C16—C17	0.6 (5)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆N₄
M_r	442.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.0156 (6), 10.7001 (6), 18.6280 (9)
β (°)	95.177 (4)
V (Å³)	2385.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.36 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Blessing, 1995)
T_min, T_max	0.869, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16281, 4179, 3375
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.174, 1.00
No. of reflections	4179
No. of parameters	411
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997), SHELXTL (Bruker, 2000).

Selected bond lengths (Å) top

N11—C12	1.383 (3)	N43—C43	1.387 (3)
N41—C42	1.385 (3)	N11—C11	1.387 (3)
N13—C12	1.314 (3)	N41—C41	1.385 (3)
N43—C42	1.312 (3)	C11—C13	1.395 (3)
N13—C13	1.387 (3)	C41—C43	1.393 (3)

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