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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007852/ac6037sup1.cif
Contains datablocks IIa, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007852/ac6037IIasup2.hkl
Contains datablock IIa

CCDC reference: 214630

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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
Yellow Alert 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 ππ 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 ππ 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
[Figure 1] Fig. 1. The molecular structure of the title compound showing 25% probability displacement ellipsiods.
[Figure 2] 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
C30H26N4Dx = 1.232 Mg m3
Dm = 1.19 (1) Mg m3
Dm measured by floatation-carbontetrachloride/cyclohexane
Mr = 442.55Melting point: 160 °C soften, 176 °C melt K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.0156 (6) ÅCell parameters from 821 reflections
b = 10.7001 (6) Åθ = 2.2–23.1°
c = 18.6280 (9) ŵ = 0.07 mm1
β = 95.177 (4)°T = 294 K
V = 2385.2 (2) Å3Block, colorless
Z = 40.38 × 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 tube3375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Blessing, 1995)
h = 1314
Tmin = 0.869, Tmax = 1.000k = 1212
16281 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.1086P)2 + 0.4514P]
where P = (Fo2 + 2Fc2)/3
4179 reflections(Δ/σ)max < 0.001
411 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C30H26N4V = 2385.2 (2) Å3
Mr = 442.55Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.0156 (6) ŵ = 0.07 mm1
b = 10.7001 (6) ÅT = 294 K
c = 18.6280 (9) Å0.38 × 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)
Tmin = 0.869, Tmax = 1.000Rint = 0.036
16281 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.174All H-atom parameters refined
S = 1.00Δρmax = 0.16 e Å3
4179 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
N410.59103 (14)0.81751 (16)0.05983 (9)0.0427 (5)
N430.59743 (14)0.95822 (17)0.15012 (10)0.0458 (5)
C310.81740 (17)1.04253 (18)0.08511 (12)0.0407 (5)
N130.89082 (14)0.77034 (16)0.09423 (10)0.0455 (5)
C430.52664 (17)0.8610 (2)0.16486 (12)0.0468 (6)
N110.79324 (15)0.69086 (17)0.18087 (10)0.0486 (5)
C420.63436 (15)0.92883 (19)0.08813 (11)0.0380 (5)
C330.68646 (19)1.0394 (2)0.02063 (12)0.0459 (5)
C360.8909 (2)1.1063 (2)0.04448 (15)0.0521 (6)
C210.85132 (16)1.0249 (2)0.16386 (12)0.0438 (5)
C320.71418 (16)1.00419 (18)0.05033 (11)0.0381 (5)
C130.85651 (17)0.6501 (2)0.07525 (13)0.0455 (6)
C110.79570 (17)0.5991 (2)0.12848 (13)0.0490 (6)
C350.8633 (2)1.1361 (2)0.02681 (14)0.0557 (7)
C140.8730 (2)0.5817 (2)0.01363 (16)0.0593 (7)
C340.7595 (2)1.1063 (2)0.05890 (14)0.0514 (6)
C220.86932 (17)0.9084 (2)0.19764 (12)0.0466 (6)
C120.85190 (16)0.7914 (2)0.15681 (12)0.0431 (5)
C230.9077 (2)0.9049 (3)0.27054 (14)0.0616 (7)
C480.61912 (19)0.7499 (2)0.00434 (13)0.0490 (6)
C470.4603 (2)0.6622 (3)0.11279 (17)0.0604 (7)
C440.4674 (2)0.8414 (3)0.22533 (15)0.0605 (7)
C170.7480 (2)0.4805 (2)0.12222 (18)0.0647 (8)
C260.8700 (2)1.1325 (3)0.20533 (15)0.0572 (7)
C410.52231 (16)0.7726 (2)0.10981 (12)0.0461 (6)
C180.7329 (2)0.6805 (3)0.24523 (15)0.0630 (7)
C490.5278 (3)0.7518 (3)0.06608 (18)0.0713 (8)
C240.9255 (2)1.0128 (3)0.31014 (16)0.0719 (8)
C250.9061 (2)1.1258 (3)0.27797 (16)0.0684 (8)
C450.4077 (2)0.7330 (3)0.22822 (19)0.0747 (9)
C190.7921 (4)0.5953 (5)0.3016 (2)0.0993 (13)
C460.4042 (2)0.6450 (3)0.1730 (2)0.0755 (9)
C150.8263 (2)0.4640 (3)0.0073 (2)0.0721 (8)
C160.7656 (2)0.4149 (3)0.06084 (19)0.0736 (9)
H140.910 (2)0.619 (2)0.0257 (16)0.076 (9)*
H470.4615 (19)0.604 (2)0.0752 (12)0.047 (7)*
H170.706 (2)0.451 (2)0.1592 (14)0.067 (8)*
H460.363 (3)0.567 (3)0.1754 (16)0.088 (9)*
H450.368 (2)0.720 (3)0.2701 (17)0.083 (9)*
H160.733 (3)0.331 (3)0.0559 (17)0.095 (10)*
H440.469 (3)0.904 (3)0.2635 (16)0.086 (10)*
H330.612 (2)1.018 (2)0.0432 (11)0.049 (6)*
H360.963 (2)1.129 (2)0.0680 (12)0.051 (6)*
H350.915 (2)1.176 (2)0.0535 (13)0.054 (7)*
H250.916 (2)1.201 (2)0.3040 (14)0.062 (7)*
H260.857 (2)1.215 (3)0.1821 (13)0.066 (8)*
H340.739 (2)1.127 (2)0.1072 (15)0.061 (7)*
H230.921 (2)0.828 (3)0.2966 (14)0.069 (8)*
H150.836 (2)0.415 (3)0.0347 (17)0.084 (9)*
H240.957 (3)1.009 (3)0.3606 (17)0.083 (9)*
H48A0.634 (2)0.661 (2)0.0106 (13)0.060 (7)*
H48B0.690 (2)0.787 (2)0.0191 (12)0.055 (6)*
H18B0.656 (2)0.643 (2)0.2283 (14)0.071 (8)*
H18A0.727 (2)0.769 (3)0.2645 (14)0.073 (8)*
H49C0.549 (3)0.697 (3)0.104 (2)0.110 (12)*
H49B0.514 (2)0.840 (3)0.0850 (15)0.083 (9)*
H49A0.458 (3)0.719 (3)0.0468 (17)0.095 (10)*
H19A0.750 (3)0.598 (4)0.343 (2)0.119 (13)*
H19B0.865 (4)0.628 (4)0.319 (2)0.137 (17)*
H19C0.800 (4)0.505 (5)0.279 (3)0.17 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N410.0387 (9)0.0450 (10)0.0438 (11)0.0024 (8)0.0005 (8)0.0022 (8)
N430.0386 (10)0.0537 (11)0.0451 (12)0.0019 (8)0.0033 (8)0.0023 (9)
C310.0422 (11)0.0339 (11)0.0459 (13)0.0011 (9)0.0036 (9)0.0029 (9)
N130.0386 (10)0.0460 (10)0.0518 (12)0.0014 (8)0.0035 (8)0.0077 (9)
C430.0359 (11)0.0570 (14)0.0469 (14)0.0024 (10)0.0010 (10)0.0104 (11)
N110.0437 (10)0.0527 (11)0.0498 (12)0.0002 (8)0.0058 (8)0.0146 (9)
C420.0322 (10)0.0432 (11)0.0376 (12)0.0009 (8)0.0022 (9)0.0024 (9)
C330.0472 (13)0.0468 (12)0.0435 (14)0.0016 (10)0.0029 (10)0.0002 (10)
C360.0467 (14)0.0459 (13)0.0644 (17)0.0085 (10)0.0094 (12)0.0010 (11)
C210.0325 (11)0.0521 (13)0.0465 (13)0.0058 (9)0.0014 (9)0.0032 (10)
C320.0386 (11)0.0378 (10)0.0379 (12)0.0017 (8)0.0030 (9)0.0001 (9)
C130.0356 (11)0.0433 (12)0.0568 (15)0.0038 (9)0.0006 (10)0.0097 (11)
C110.0381 (12)0.0455 (12)0.0629 (16)0.0049 (9)0.0022 (11)0.0095 (11)
C350.0683 (17)0.0436 (13)0.0585 (17)0.0058 (11)0.0245 (14)0.0059 (12)
C140.0523 (14)0.0562 (15)0.0704 (19)0.0078 (11)0.0113 (13)0.0002 (14)
C340.0679 (16)0.0467 (13)0.0408 (14)0.0031 (11)0.0111 (12)0.0032 (11)
C220.0366 (11)0.0568 (14)0.0459 (14)0.0048 (9)0.0012 (10)0.0043 (11)
C120.0344 (11)0.0497 (13)0.0445 (13)0.0018 (9)0.0010 (9)0.0105 (10)
C230.0512 (14)0.0815 (19)0.0501 (16)0.0055 (13)0.0069 (12)0.0088 (14)
C480.0469 (13)0.0484 (14)0.0507 (15)0.0008 (10)0.0009 (11)0.0027 (11)
C470.0498 (14)0.0566 (15)0.0737 (19)0.0064 (11)0.0003 (13)0.0112 (15)
C440.0447 (13)0.0817 (19)0.0560 (17)0.0018 (12)0.0100 (12)0.0120 (15)
C170.0530 (15)0.0513 (15)0.091 (2)0.0020 (11)0.0138 (15)0.0156 (15)
C260.0483 (13)0.0596 (16)0.0630 (18)0.0103 (11)0.0016 (12)0.0123 (13)
C410.0359 (11)0.0512 (13)0.0504 (14)0.0019 (9)0.0013 (10)0.0122 (11)
C180.0561 (16)0.0757 (19)0.0580 (17)0.0034 (13)0.0101 (13)0.0180 (14)
C490.074 (2)0.074 (2)0.063 (2)0.0008 (16)0.0119 (16)0.0115 (16)
C240.0623 (17)0.104 (2)0.0480 (17)0.0217 (15)0.0052 (13)0.0047 (17)
C250.0573 (15)0.086 (2)0.0614 (19)0.0225 (14)0.0016 (13)0.0274 (17)
C450.0512 (15)0.102 (2)0.072 (2)0.0045 (15)0.0155 (14)0.0303 (19)
C190.105 (3)0.121 (3)0.073 (3)0.002 (3)0.014 (2)0.052 (2)
C460.0516 (15)0.0725 (19)0.102 (3)0.0145 (14)0.0044 (16)0.0370 (19)
C150.0631 (17)0.0559 (16)0.099 (2)0.0033 (13)0.0156 (16)0.0131 (17)
C160.0624 (17)0.0450 (15)0.114 (3)0.0002 (13)0.0128 (17)0.0053 (16)
Geometric parameters (Å, º) top
N11—C121.383 (3)C23—C241.377 (4)
N41—C421.385 (3)C23—H230.96 (3)
N13—C121.314 (3)C48—C491.516 (4)
N43—C421.312 (3)C48—H48A1.00 (3)
N13—C131.387 (3)C48—H48B1.00 (2)
N43—C431.387 (3)C47—C461.372 (4)
N11—C111.387 (3)C47—C411.401 (3)
N41—C411.385 (3)C47—H470.94 (2)
C11—C131.395 (3)C44—C451.368 (4)
C41—C431.393 (3)C44—H440.98 (3)
N41—C481.463 (3)C17—C161.374 (4)
C31—C361.393 (3)C17—H170.95 (3)
C31—C321.408 (3)C26—C251.385 (4)
C31—C211.499 (3)C26—H260.99 (3)
C43—C441.401 (3)C18—C191.518 (4)
N11—C181.460 (3)C18—H18B1.03 (3)
C42—C321.479 (3)C18—H18A1.02 (3)
C33—C341.379 (3)C49—H49C0.98 (4)
C33—C321.386 (3)C49—H49B1.01 (3)
C33—H330.99 (2)C49—H49A1.00 (3)
C36—C351.377 (4)C24—C251.360 (4)
C36—H360.97 (2)C24—H240.98 (3)
C21—C261.393 (3)C25—H250.94 (3)
C21—C221.403 (3)C45—C461.392 (5)
C13—C141.390 (4)C45—H450.96 (3)
C11—C171.393 (3)C19—H19A0.96 (4)
C35—C341.372 (4)C19—H19B0.97 (5)
C35—H350.93 (2)C19—H19C1.06 (5)
C14—C151.379 (4)C46—H460.97 (3)
C14—H140.98 (3)C15—C161.390 (4)
C34—H340.94 (3)C15—H150.95 (3)
C22—C231.395 (3)C16—H160.98 (3)
C22—C121.470 (3)
C42—N41—C41105.60 (17)C49—C48—H48A108.6 (14)
C42—N41—C48129.06 (18)N41—C48—H48B107.1 (13)
C41—N41—C48124.96 (18)C49—C48—H48B111.3 (13)
C42—N43—C43104.87 (18)H48A—C48—H48B108.7 (19)
C36—C31—C32117.9 (2)C46—C47—C41116.6 (3)
C36—C31—C21117.64 (19)C46—C47—H47124.3 (14)
C32—C31—C21124.35 (18)C41—C47—H47119.1 (14)
C12—N13—C13105.30 (18)C45—C44—C43117.7 (3)
N43—C43—C41110.28 (19)C45—C44—H44122.2 (18)
N43—C43—C44129.5 (2)C43—C44—H44120.1 (18)
C41—C43—C44120.1 (2)C16—C17—C11116.2 (3)
C12—N11—C11106.21 (18)C16—C17—H17124.7 (16)
C12—N11—C18129.1 (2)C11—C17—H17119.0 (16)
C11—N11—C18124.6 (2)C25—C26—C21121.3 (3)
N43—C42—N41113.32 (18)C25—C26—H26119.8 (15)
N43—C42—C32125.01 (18)C21—C26—H26118.9 (15)
N41—C42—C32121.68 (18)N41—C41—C43105.92 (18)
C34—C33—C32121.7 (2)N41—C41—C47132.1 (2)
C34—C33—H33120.0 (13)C43—C41—C47121.9 (2)
C32—C33—H33118.3 (13)N11—C18—C19112.1 (3)
C35—C36—C31121.9 (2)N11—C18—H18B106.0 (15)
C35—C36—H36120.4 (13)C19—C18—H18B109.3 (15)
C31—C36—H36117.7 (13)N11—C18—H18A106.0 (15)
C26—C21—C22118.3 (2)C19—C18—H18A111.1 (15)
C26—C21—C31117.0 (2)H18B—C18—H18A112 (2)
C22—C21—C31124.62 (19)C48—C49—H49C109 (2)
C33—C32—C31119.0 (2)C48—C49—H49B111.3 (17)
C33—C32—C42119.48 (19)H49C—C49—H49B111 (3)
C31—C32—C42121.46 (19)C48—C49—H49A107.0 (19)
N13—C13—C14129.6 (2)H49C—C49—H49A109 (3)
N13—C13—C11110.1 (2)H49B—C49—H49A109 (3)
C14—C13—C11120.3 (2)C25—C24—C23119.8 (3)
N11—C11—C17132.0 (2)C25—C24—H24119.4 (17)
N11—C11—C13105.62 (19)C23—C24—H24120.7 (17)
C17—C11—C13122.3 (2)C24—C25—C26120.2 (3)
C34—C35—C36119.8 (2)C24—C25—H25121.4 (16)
C34—C35—H35120.0 (14)C26—C25—H25118.4 (16)
C36—C35—H35120.2 (14)C44—C45—C46121.7 (3)
C15—C14—C13117.6 (3)C44—C45—H45117.2 (18)
C15—C14—H14121.2 (16)C46—C45—H45121.1 (18)
C13—C14—H14120.9 (16)C18—C19—H19A107 (2)
C35—C34—C33119.4 (2)C18—C19—H19B111 (3)
C35—C34—H34120.9 (16)H19A—C19—H19B105 (3)
C33—C34—H34119.7 (16)C18—C19—H19C109 (3)
C23—C22—C21119.0 (2)H19A—C19—H19C114 (4)
C23—C22—C12120.0 (2)H19B—C19—H19C111 (4)
C21—C22—C12121.0 (2)C47—C46—C45121.9 (3)
N13—C12—N11112.7 (2)C47—C46—H46116.2 (18)
N13—C12—C22124.04 (19)C45—C46—H46121.9 (18)
N11—C12—C22123.2 (2)C14—C15—C16121.3 (3)
C24—C23—C22121.4 (3)C14—C15—H15119.4 (18)
C24—C23—H23116.0 (16)C16—C15—H15119.3 (18)
C22—C23—H23122.6 (16)C17—C16—C15122.2 (3)
N41—C48—C49114.1 (2)C17—C16—H16117.1 (19)
N41—C48—H48A106.8 (14)C15—C16—H16120.7 (19)
C42—N43—C43—C410.0 (2)C31—C21—C22—C122.1 (3)
C42—N43—C43—C44177.4 (2)C13—N13—C12—N110.1 (2)
C43—N43—C42—N410.8 (2)C13—N13—C12—C22179.55 (18)
C43—N43—C42—C32179.26 (18)C11—N11—C12—N130.1 (2)
C41—N41—C42—N431.2 (2)C18—N11—C12—N13176.3 (2)
C48—N41—C42—N43174.41 (19)C11—N11—C12—C22179.56 (19)
C41—N41—C42—C32178.81 (17)C18—N11—C12—C224.2 (3)
C48—N41—C42—C325.6 (3)C23—C22—C12—N13130.5 (2)
C32—C31—C36—C352.5 (3)C21—C22—C12—N1347.4 (3)
C21—C31—C36—C35174.6 (2)C23—C22—C12—N1148.8 (3)
C36—C31—C21—C2660.1 (3)C21—C22—C12—N11133.2 (2)
C32—C31—C21—C26116.7 (2)C21—C22—C23—C241.6 (4)
C36—C31—C21—C22117.4 (2)C12—C22—C23—C24179.6 (2)
C32—C31—C21—C2265.7 (3)C42—N41—C48—C49109.9 (3)
C34—C33—C32—C312.9 (3)C41—N41—C48—C4978.1 (3)
C34—C33—C32—C42177.9 (2)N43—C43—C44—C45176.4 (2)
C36—C31—C32—C334.9 (3)C41—C43—C44—C450.9 (3)
C21—C31—C32—C33171.94 (19)N11—C11—C17—C16178.3 (2)
C36—C31—C32—C42175.93 (19)C13—C11—C17—C161.0 (4)
C21—C31—C32—C427.2 (3)C22—C21—C26—C250.4 (3)
N43—C42—C32—C33126.1 (2)C31—C21—C26—C25177.3 (2)
N41—C42—C32—C3353.8 (3)C42—N41—C41—C431.1 (2)
N43—C42—C32—C3153.0 (3)C48—N41—C41—C43174.65 (18)
N41—C42—C32—C31127.0 (2)C42—N41—C41—C47176.7 (2)
C12—N13—C13—C14178.7 (2)C48—N41—C41—C473.1 (4)
C12—N13—C13—C110.1 (2)N43—C43—C41—N410.7 (2)
C12—N11—C11—C17177.5 (2)C44—C43—C41—N41178.43 (19)
C18—N11—C11—C171.1 (4)N43—C43—C41—C47177.3 (2)
C12—N11—C11—C130.1 (2)C44—C43—C41—C470.4 (3)
C18—N11—C11—C13176.5 (2)C46—C47—C41—N41177.1 (2)
N13—C13—C11—N110.0 (2)C46—C47—C41—C430.3 (3)
C14—C13—C11—N11178.87 (19)C12—N11—C18—C19108.9 (4)
N13—C13—C11—C17177.9 (2)C11—N11—C18—C1975.5 (4)
C14—C13—C11—C171.0 (3)C22—C23—C24—C250.3 (4)
C31—C36—C35—C342.1 (4)C23—C24—C25—C260.9 (4)
N13—C13—C14—C15178.0 (2)C21—C26—C25—C240.9 (4)
C11—C13—C14—C150.7 (4)C43—C44—C45—C460.6 (4)
C36—C35—C34—C334.2 (4)C41—C47—C46—C450.6 (4)
C32—C33—C34—C351.7 (3)C44—C45—C46—C470.1 (4)
C26—C21—C22—C231.6 (3)C13—C14—C15—C160.5 (4)
C31—C21—C22—C23175.9 (2)C11—C17—C16—C150.8 (4)
C26—C21—C22—C12179.55 (19)C14—C15—C16—C170.6 (5)

Experimental details

Crystal data
Chemical formulaC30H26N4
Mr442.55
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)12.0156 (6), 10.7001 (6), 18.6280 (9)
β (°) 95.177 (4)
V3)2385.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.38 × 0.36 × 0.26
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Blessing, 1995)
Tmin, Tmax0.869, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16281, 4179, 3375
Rint0.036
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.174, 1.00
No. of reflections4179
No. of parameters411
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)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—C121.383 (3)N43—C431.387 (3)
N41—C421.385 (3)N11—C111.387 (3)
N13—C121.314 (3)N41—C411.385 (3)
N43—C421.312 (3)C11—C131.395 (3)
N13—C131.387 (3)C41—C431.393 (3)
 

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