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N,N'-Bis(3-methyl­phenyl)-N,N'-di­phenyl-1,1'-bi­phenyl-4,4'-di­amine (TPD), C38H32N2, crystallizes in the monoclinic space group P21 with a pseudo-orthogonal lattice, rather than the previously reported orthorhombic space group P212121 [Kennedy, Smith, Tackley, David, Shankland, Brown & Teat (2002). J. Mater. Chem. 12, 168-172]. The asymmetric unit consists of two independent mol­ecules, A and B, which are arranged along the [100] direction to form vertical layers of alternately stacked A and B mol­ecules. Molecule A shows a great deal of rotational movement in the four terminal aryl rings, resulting in two disordered tolyl groups split over two sites, while mol­ecule B exhibits an almost cis configuration of the two terminal tolyl groups with respect to these ring planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104010479/av1182sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104010479/av1182Isup2.hkl
Contains datablock I

CCDC reference: 243624

Comment top

The crystal structure of the title compound, TPD, (I), was first reported by a synchrotron single-crystal diffraction experiment with a microcrystal, on Station 9.8 of the Daresbury SRS, based on an orthorhombic structure of (I). The data were deposited in the Cambridge Structural Database, refcode 174279 (Kennedy et al., 2002), although the coordinates of several atoms were incorrect. The aim of the present work was to provide a complete structural analysis to correct this error in the existing literature mentioned above and to support the findings obtained from density-functional theory for predicting the reorganization energy (Malagoli & Brédas, 2000; Lin et al., 2003). \sch

Colorless crystals of (I) obtained in this study with more careful recrystallization experiments from morpholine revealed that the compound crystallizes in the monoclinic space group P21 [a = 14.447 (2), b = 11.0153 (16) and c = 17.803 (3) Å, β = 90.602 (3)° and Z = 4] with a pseudo-orthogonal lattice at 90 (2) K, rather than the orthorhombic space group P212121 (Kennedy et al., 2002). The β angle of monoclinic P21 is close to 90° and thus the crystals appear orthorhombic when twinned. The twinning phenomenon of (I) was frequently observed during our X-ray investigations. It is not possible to prevent twinning, even under idealized conditions such as low temperature, slow crystal growth or crystallization from different solvents. It is quite clear that the second polymorph of (I) proposed by Kennedy et al. does not exist, because the simulated profile of the monoclinic P21 structure has completely accounted for the peaks in the powder diffraction data. The additional peaks mentioned by Kennedy et al. arise from the reduction of symmetry from orthorhombic to monoclinic, with β = 90.602°, rather than from a form II of (I).

Selected geometric parameters for (I) are given in Table 1. In the structure of (I), the asymmetric unit consists of two independent molecules, A and B (Fig. 1), which are arranged along [100] to form vertical layers of alternately stacked A and B molecules (Fig. 2). Molecule A shows a great deal of rotational movement in the four terminal aryl rings, resulting in two disordered tolyl groups spilt over two sites, the occupancies of which refined to 64.4 (8)% for atom C32B and 35.6 (8)% for atom C32A. Molecule B exhibits a nearly cis configuration of the two terminal tolyls with respect to these ring planes.

Although the individual rings are essentially planar, the two central biphenyl groups are twisted as a consequence of the H atoms in the ortho positions, which introduce repulsive steric forces, resulting in non-planar ππ interactions across the C—C inter-ring bond. The magnitude of this twist is almost equivalent for the two independent molecules, such that the torsion angles are C16—C17—C20—C21 36.5 (5), C18—C17—C20—C25 36.2 (5), C56—C55—C58—C63 36.4 (5) and C54—C55—C58—C59 35.7 (5)°. The inter-ring distances are C17—C20 1.487 (4) and C55—C58 1.485 (4) Å, in close agreement with the values obtained in a recent theoretical study (Lin et al., 2003) and those of the neutron single-crystal diffraction data of an unsubstituted biphenyl (Cailleau & Baudour, 1979).

Four independent N atoms for both A and B molecules are nominally sp3 hybridized, but with some planarization of the molecule to take advantage of the resonance delocalization with the benzene rings, which leads to C—N—C bond angles close to 120°, displaying features of sp2 hybridization. The angle sums around these N atoms are ca 359° for atoms N1 and N4, and ca 360° for atoms N2 and N3 (Table 1). Molecular-orbital calculations also revealed that the highest occupied molecular orbital (HOMO) of (I) is strongly delocalized across all benzene rings of the molecule of (I), with significant contributions from the lone pair electrons of the N (Sugiyama et al., 1998). This geometric feature of molecules of (I) in the crystal lattice (similar to that of its radical cation state, i.e. sp2 hybridization and a planar conformation) provides favorable conditions for geometric reorganization during the charge-transfer process (Malagoli & Brédas, 2000). The N—C bond distances vary from 1.415 to 1.430 Å, and these results are in excellent agreement with the experimental crystal structure of triphenylamine (Sobolev et al., 1985).

The three rings connected to each N atom adopt a propeller-like orientation, with torsion angles (the plane of the rings with respect to the plane defined by the N atom and its three attached C atoms) varying from 31.4 (6)–54.0 (5)° for atom N1, 19.0 (5)–57.1 (5)° for N2, 19.4 (5)–55.9 (5)° for N3 and 32.6 (6)–52.9 (4)° for N4. The twisted conformation results from the steric effect of the H atoms in the ortho positions of the benzene rings. This twisted conformation can protect the N atoms from chemical attack, e.g. H-donors etc., to lose the hole-transport function, so that (I) has an excellent lifetime when used as a photoreceptor during the repetitive xerographic cycling process.

Experimental top

Crystals of (I) were obtained by recrystallization from morpholine through careful evaporation of the solvent, to yield colorless crystals suitable for X-ray diffraction determination. The compound was also recrystallized from other organic solvents. However, smaller twinned crystals were obtained by recrystallization from acetic acid. Powder diffraction patterns indicate that the recrystallized samples only contained one phase of (I).

Refinement top

The analyzed crystal was mounted in a sealed glass capillary. We analyzed at least two samples but were unable to find pure untwinned crystals. Many reflections showed a typical split. A twin analysis of all reflections with the TWINABS program (Sheldrick, 1999) revealed twinning with two crystal components for our sample, i.e. 28932 reflections for component 1, 28809 for component 2 and 3295 for both. Since numerous reflections of this non-merohedral twin resulted in relatively poor data quality due to partial overlapping, an HKLF-5 file was generated for structural refinement, including 12812 corrected reflections (10496 reflections from the main component and 2316 overlapping reflections from the twin component). 2742 of them were rejected as systematic absence violations. The ratio of minimum to maximum apparent transmission is 0.8562. A subset of the data from crystals of (I) displayed a twofold axial symmetry with an extinction (0k0, k = 2n) which is the characteristic of space groups P21 (No. 4) or P21/m (No. 11). The non-centrosymmetric space group was found to be correct during the structural analysis. However, the refinement was unsatisfactory unless all 10070 measured reflections, which suffered from a non-merohedral twinning effect treated by the HKLF-5 approach mentioned above, were taken into account. The ratio of the two twin components was refined to 0.0349 (22) using the BASF instruction. The introduction of twinning reduced the R value from 14.22% to 6.29%. The disordered atoms (C32A and C32B) were split over two sites, the occupancies of which were refined with anisotropic models to final occupancies of 0.644 (2) for atom C32B and 0.354 (2) for atom C32A. H atoms were placed in geometrically calculated positions, with aryl C—H distances of 0.95 Å and aliphatic C—H distances of 0.98 Å, and were isotropically refined using a riding model, with Uiso(H) = 1.2Ueq(C). Please check added text.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and local programs.

Figures top
[Figure 1] Fig. 1. The two independent molecules, A and B, of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for and H atoms are shown as small spheres of arbitrary size. Atom C32B is modeled at 64.4 (8)% occupancy and atom C32A at 35.6 (8)% occupancy. The rotational disorder of the H atoms bonded to atoms C28 and C37 has been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram for (I), viewed along a, with molecules A and B alternately stacked parallel to the (100) plane. H atoms have been omitted for clarity.
N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine top
Crystal data top
C38H32N2F(000) = 1096
Mr = 516.66Dx = 1.211 Mg m3
Monoclinic, P21Melting point: 449 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 14.447 (2) ÅCell parameters from 10068 reflections
b = 11.0153 (16) Åθ = 1.4–29.0°
c = 17.803 (3) ŵ = 0.07 mm1
β = 90.602 (3)°T = 90 K
V = 2833.0 (7) Å3Parallepiped, colorless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Plateform with APEX CCD detector
diffractometer
10070 independent reflections
Radiation source: fine-focus sealed tube4919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 512 pixels mm-1θmax = 29.0°, θmin = 1.4°
ϕ and ω scansh = 1919
Absorption correction: multi-scan
(TWINABS in SAINT-Plus; Sheldrick, 1999)
k = 015
Tmin = 0.971, Tmax = 0.995l = 024
10070 measured reflections
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0466P)2]
where P = (Fo2 + 2Fc2)/3
10070 reflections(Δ/σ)max < 0.001
735 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C38H32N2V = 2833.0 (7) Å3
Mr = 516.66Z = 4
Monoclinic, P21Mo Kα radiation
a = 14.447 (2) ŵ = 0.07 mm1
b = 11.0153 (16) ÅT = 90 K
c = 17.803 (3) Å0.30 × 0.20 × 0.20 mm
β = 90.602 (3)°
Data collection top
Plateform with APEX CCD detector
diffractometer
10070 independent reflections
Absorption correction: multi-scan
(TWINABS in SAINT-Plus; Sheldrick, 1999)
4919 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.995Rint = 0.000
10070 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0631 restraint
wR(F2) = 0.130H-atom parameters constrained
S = 0.90Δρmax = 0.52 e Å3
10070 reflectionsΔρmin = 0.29 e Å3
735 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*/UeqOcc. (<1)
N10.42973 (18)0.8901 (3)0.20375 (16)0.0386 (8)
N20.6406 (2)0.8633 (3)0.33192 (15)0.0357 (7)
C10.3332 (2)0.8752 (4)0.2171 (2)0.0405 (9)
C20.2713 (3)0.9461 (4)0.1798 (2)0.0520 (11)
H20.29261.00550.14500.062*
C30.1743 (3)0.9304 (5)0.1933 (2)0.0553 (13)
C40.1465 (3)0.8437 (4)0.2436 (2)0.0525 (12)
H40.08200.83160.25160.063*
C50.2058 (3)0.7752 (4)0.2822 (2)0.0510 (11)
H50.18380.71710.31750.061*
C60.2999 (3)0.7904 (4)0.2696 (2)0.0435 (10)
H60.34260.74260.29710.052*
C70.1114 (4)1.0133 (6)0.1548 (3)0.110 (2)
H7A0.07811.06280.19210.165*
H7B0.14701.06640.12120.165*
H7C0.06680.96630.12560.165*
C80.4927 (2)0.8880 (4)0.2644 (2)0.0399 (9)
C90.4722 (3)0.9534 (4)0.3288 (2)0.0430 (10)
H90.41520.99590.33330.052*
C100.5365 (3)0.9564 (4)0.3878 (2)0.0603 (13)
H100.52211.00070.43220.072*
C110.6186 (3)0.8970 (6)0.3821 (3)0.0798 (19)
H110.66230.90210.42150.096*
C120.6386 (3)0.8282 (6)0.3178 (3)0.0798 (19)
H120.69500.78420.31410.096*
C130.5749 (3)0.8245 (5)0.2587 (2)0.0596 (13)
H130.58840.77820.21490.072*
C140.4631 (2)0.8832 (4)0.12804 (19)0.0341 (8)
C150.5388 (2)0.9530 (4)0.1054 (2)0.0357 (9)
H150.56901.00370.14070.043*
C160.5706 (2)0.9487 (3)0.03098 (19)0.0334 (8)
H160.62210.99710.01630.040*
C170.5282 (2)0.8753 (3)0.02174 (18)0.0302 (8)
C180.4534 (2)0.8053 (3)0.00282 (19)0.0343 (8)
H180.42390.75280.03190.041*
C190.4207 (2)0.8097 (3)0.0757 (2)0.0340 (9)
H190.36870.76200.09010.041*
C200.5596 (2)0.8718 (3)0.10151 (18)0.0312 (8)
C210.5909 (2)0.9754 (3)0.1386 (2)0.0342 (9)
H210.59361.04990.11180.041*
C220.6181 (2)0.9731 (3)0.2130 (2)0.0351 (9)
H220.63921.04550.23650.042*
C230.6150 (2)0.8654 (3)0.25428 (19)0.0305 (8)
C240.5838 (2)0.7603 (3)0.21783 (19)0.0321 (8)
H240.58090.68580.24470.039*
C250.5572 (2)0.7640 (3)0.14323 (19)0.0311 (8)
H250.53660.69150.11950.037*
C260.6738 (2)0.7550 (3)0.3666 (2)0.0343 (9)
C270.6447 (3)0.7255 (4)0.4379 (2)0.0489 (11)
H270.60260.77780.46260.059*
C290.7357 (3)0.5480 (4)0.4382 (3)0.0556 (13)
H290.75670.47620.46250.067*
C300.7666 (3)0.5749 (4)0.3683 (3)0.0487 (11)
H300.80860.52140.34440.058*
C310.7369 (2)0.6812 (3)0.3307 (2)0.0373 (9)
H310.75970.70140.28240.045*
C330.6427 (3)0.9731 (3)0.3737 (2)0.0372 (9)
C340.5657 (3)1.0464 (4)0.3794 (2)0.0436 (10)
H340.50951.02370.35500.052*
C350.5700 (4)1.1519 (4)0.4200 (2)0.0565 (12)
H350.51681.20210.42370.068*
C360.6506 (4)1.1850 (4)0.4550 (2)0.0595 (13)
H360.65311.25930.48210.071*
C370.7290 (3)1.1124 (4)0.4520 (2)0.0547 (12)
H370.78451.13480.47760.066*0.356 (8)
C32A0.6615 (8)0.5729 (12)0.5464 (6)0.058 (4)0.356 (8)
H32A0.65980.63840.58360.087*0.356 (8)
H32B0.71270.51760.55850.087*0.356 (8)
H32C0.60290.52800.54710.087*0.356 (8)
C280.6748 (3)0.6229 (4)0.4739 (2)0.0494 (11)
H280.65380.60400.52290.059*0.644 (8)
C32B0.8177 (5)1.1514 (6)0.4846 (4)0.064 (3)0.644 (8)
H32D0.82431.11860.53560.096*0.644 (8)
H32E0.81981.24030.48660.096*0.644 (8)
H32F0.86841.12150.45350.096*0.644 (8)
C380.7235 (3)1.0057 (4)0.4104 (2)0.0449 (10)
H380.77620.95450.40710.054*
N30.1397 (2)0.3956 (3)0.17160 (15)0.0344 (7)
N40.06884 (18)0.3667 (3)0.70335 (15)0.0371 (7)
C390.1399 (2)0.2857 (3)0.12883 (19)0.0345 (9)
C400.2204 (3)0.2539 (3)0.0922 (2)0.0391 (9)
H400.27310.30530.09570.047*
C410.2252 (3)0.1465 (4)0.0499 (2)0.0461 (11)
C420.1468 (3)0.0746 (4)0.0464 (2)0.0510 (12)
H420.14830.00110.01860.061*
C430.0664 (3)0.1074 (4)0.0825 (2)0.0471 (11)
H430.01340.05660.07890.057*
C440.0625 (3)0.2135 (3)0.1237 (2)0.0413 (10)
H440.00700.23630.14820.050*
C450.3133 (4)0.1104 (5)0.0137 (3)0.0791 (16)
H45A0.31970.15380.03400.119*
H45B0.31280.02270.00420.119*
H45C0.36550.13070.04690.119*
C460.1719 (2)0.5035 (3)0.1359 (2)0.0327 (8)
C470.2364 (2)0.5780 (3)0.1702 (2)0.0349 (9)
H470.26040.55890.21860.042*
C480.2660 (3)0.6826 (4)0.1322 (2)0.0425 (10)
H480.30960.73530.15570.051*
C490.2328 (3)0.7097 (4)0.0620 (2)0.0451 (11)
H490.25350.78090.03730.054*
C500.1698 (3)0.6350 (4)0.0269 (2)0.0473 (11)
H500.14740.65300.02210.057*
C510.1399 (3)0.5328 (4)0.0646 (2)0.0438 (10)
H510.09590.48110.04080.053*
C520.1157 (2)0.3934 (3)0.24843 (19)0.0319 (8)
C530.0863 (2)0.4986 (3)0.28523 (19)0.0315 (8)
H530.08440.57350.25880.038*
C540.0602 (2)0.4949 (3)0.35928 (19)0.0303 (8)
H540.04030.56760.38280.036*
C550.0621 (2)0.3876 (3)0.40101 (19)0.0314 (8)
C560.0925 (2)0.2834 (3)0.36395 (19)0.0328 (8)
H560.09520.20860.39050.039*
C570.1187 (2)0.2868 (3)0.28959 (19)0.0329 (9)
H570.13930.21430.26620.039*
C580.0303 (2)0.3836 (3)0.48003 (18)0.0299 (8)
C590.0437 (2)0.4534 (3)0.50360 (19)0.0339 (8)
H590.07300.50620.46850.041*
C600.0763 (2)0.4493 (3)0.5761 (2)0.0351 (9)
H600.12720.49890.58990.042*
C610.0355 (2)0.3731 (3)0.62892 (19)0.0325 (8)
C620.0398 (2)0.3021 (4)0.60653 (19)0.0347 (9)
H620.06910.24970.64190.042*
C630.0721 (2)0.3072 (3)0.53369 (19)0.0331 (8)
H630.12340.25840.51980.040*
C640.1651 (2)0.3798 (4)0.7152 (2)0.0415 (10)
C650.2264 (3)0.3093 (5)0.6767 (2)0.0573 (12)
H650.20600.25000.64180.069*
C660.3252 (3)0.3279 (4)0.6907 (2)0.0603 (14)
C670.3508 (3)0.4156 (4)0.7413 (2)0.0547 (12)
H670.41500.42800.74950.066*
C680.2919 (3)0.4834 (5)0.7791 (3)0.0631 (13)
H680.31270.54260.81380.076*
C690.1980 (3)0.4657 (4)0.7667 (2)0.0482 (11)
H690.15450.51350.79410.058*
C700.3884 (4)0.2479 (6)0.6531 (3)0.117 (2)
H70A0.42780.29470.61860.175*
H70B0.42700.20690.69020.175*
H70C0.35360.18720.62470.175*
C710.0056 (2)0.3680 (4)0.7648 (2)0.0369 (9)
C720.0255 (3)0.3042 (4)0.8297 (2)0.0414 (9)
H720.08240.26160.83360.050*
C730.0387 (3)0.3022 (4)0.8900 (2)0.0579 (12)
H730.02510.25790.93430.070*
C740.1207 (3)0.3642 (5)0.8849 (3)0.0708 (16)
H740.16420.36110.92530.085*
C750.1407 (3)0.4310 (5)0.8213 (3)0.0702 (16)
H750.19700.47530.81840.084*
C760.0772 (3)0.4331 (4)0.7610 (2)0.0541 (12)
H760.09060.47900.71740.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0275 (16)0.051 (2)0.0367 (18)0.0062 (16)0.0049 (13)0.0032 (17)
N20.0463 (18)0.0272 (18)0.0334 (18)0.0052 (16)0.0065 (13)0.0032 (15)
C10.038 (2)0.046 (2)0.038 (2)0.014 (2)0.0031 (16)0.018 (2)
C20.045 (2)0.068 (3)0.043 (2)0.019 (2)0.0047 (19)0.007 (2)
C30.043 (2)0.079 (4)0.044 (3)0.030 (3)0.0146 (19)0.010 (2)
C40.048 (3)0.064 (3)0.045 (3)0.008 (2)0.005 (2)0.003 (2)
C50.053 (3)0.046 (3)0.054 (3)0.000 (2)0.004 (2)0.014 (2)
C60.037 (2)0.040 (3)0.053 (3)0.002 (2)0.0055 (18)0.013 (2)
C70.086 (4)0.148 (7)0.096 (5)0.038 (4)0.017 (3)0.041 (5)
C80.028 (2)0.046 (3)0.045 (2)0.001 (2)0.0006 (16)0.004 (2)
C90.047 (2)0.042 (2)0.040 (2)0.012 (2)0.0006 (18)0.001 (2)
C100.063 (3)0.062 (3)0.056 (3)0.031 (3)0.014 (2)0.017 (2)
C110.057 (3)0.118 (5)0.064 (3)0.046 (3)0.020 (3)0.053 (3)
C120.036 (3)0.127 (6)0.076 (4)0.004 (3)0.008 (2)0.051 (4)
C130.041 (2)0.087 (4)0.050 (3)0.010 (3)0.005 (2)0.016 (3)
C140.031 (2)0.031 (2)0.040 (2)0.0077 (18)0.0011 (15)0.0041 (18)
C150.035 (2)0.032 (2)0.039 (2)0.0010 (18)0.0026 (16)0.0047 (18)
C160.0277 (19)0.031 (2)0.041 (2)0.0045 (17)0.0009 (15)0.0037 (18)
C170.0259 (18)0.0250 (19)0.040 (2)0.0045 (17)0.0010 (14)0.0050 (17)
C180.036 (2)0.027 (2)0.040 (2)0.0007 (18)0.0016 (16)0.0066 (17)
C190.0277 (19)0.030 (2)0.044 (2)0.0016 (17)0.0053 (16)0.0029 (18)
C200.0288 (19)0.029 (2)0.036 (2)0.0037 (17)0.0007 (14)0.0038 (18)
C210.036 (2)0.028 (2)0.038 (2)0.0018 (18)0.0007 (16)0.0019 (17)
C220.036 (2)0.026 (2)0.044 (2)0.0007 (17)0.0017 (16)0.0014 (18)
C230.0262 (18)0.030 (2)0.036 (2)0.0064 (18)0.0028 (14)0.0038 (18)
C240.0250 (19)0.032 (2)0.040 (2)0.0015 (17)0.0003 (15)0.0049 (17)
C250.0258 (18)0.032 (2)0.035 (2)0.0002 (17)0.0006 (15)0.0002 (17)
C260.038 (2)0.028 (2)0.037 (2)0.0032 (18)0.0099 (17)0.0028 (17)
C270.060 (3)0.045 (3)0.042 (3)0.004 (2)0.004 (2)0.005 (2)
C290.067 (3)0.031 (3)0.067 (3)0.010 (2)0.040 (3)0.011 (2)
C300.049 (3)0.030 (2)0.066 (3)0.015 (2)0.025 (2)0.016 (2)
C310.035 (2)0.033 (2)0.043 (2)0.0086 (18)0.0128 (17)0.0082 (18)
C330.045 (2)0.028 (2)0.039 (2)0.0012 (19)0.0003 (17)0.0038 (17)
C340.052 (3)0.034 (2)0.045 (2)0.010 (2)0.0035 (19)0.0052 (19)
C350.078 (3)0.043 (3)0.049 (3)0.012 (3)0.010 (2)0.005 (2)
C360.098 (4)0.030 (3)0.051 (3)0.004 (3)0.006 (3)0.006 (2)
C370.078 (3)0.036 (3)0.050 (3)0.007 (2)0.014 (2)0.008 (2)
C32A0.059 (8)0.062 (9)0.052 (9)0.009 (7)0.000 (6)0.018 (7)
C280.068 (3)0.037 (3)0.042 (3)0.009 (2)0.015 (2)0.010 (2)
C32B0.083 (6)0.043 (5)0.065 (5)0.000 (4)0.037 (4)0.001 (4)
C380.055 (3)0.032 (2)0.049 (3)0.003 (2)0.004 (2)0.004 (2)
N30.0457 (18)0.0244 (18)0.0331 (17)0.0051 (15)0.0031 (13)0.0044 (14)
N40.0267 (16)0.047 (2)0.0381 (18)0.0038 (16)0.0039 (13)0.0054 (16)
C390.043 (2)0.028 (2)0.032 (2)0.0039 (19)0.0003 (16)0.0014 (17)
C400.046 (2)0.028 (2)0.043 (2)0.0052 (19)0.0048 (18)0.0034 (18)
C410.066 (3)0.031 (2)0.042 (3)0.000 (2)0.011 (2)0.0011 (19)
C420.090 (4)0.026 (2)0.037 (2)0.003 (2)0.001 (2)0.0040 (19)
C430.067 (3)0.033 (2)0.041 (3)0.011 (2)0.006 (2)0.0030 (19)
C440.047 (2)0.032 (2)0.045 (2)0.009 (2)0.0010 (18)0.0059 (18)
C450.096 (4)0.059 (3)0.083 (4)0.003 (3)0.032 (3)0.013 (3)
C460.037 (2)0.028 (2)0.033 (2)0.0031 (18)0.0095 (16)0.0029 (17)
C470.033 (2)0.034 (2)0.038 (2)0.0072 (18)0.0106 (16)0.0093 (18)
C480.038 (2)0.030 (2)0.059 (3)0.0129 (18)0.016 (2)0.019 (2)
C490.052 (3)0.030 (2)0.054 (3)0.001 (2)0.022 (2)0.003 (2)
C500.058 (3)0.042 (3)0.042 (3)0.005 (2)0.010 (2)0.006 (2)
C510.053 (3)0.036 (2)0.043 (3)0.001 (2)0.0019 (19)0.0057 (19)
C520.0274 (19)0.032 (2)0.036 (2)0.0063 (18)0.0007 (15)0.0017 (18)
C530.0268 (19)0.028 (2)0.040 (2)0.0013 (16)0.0004 (15)0.0014 (17)
C540.0248 (18)0.030 (2)0.036 (2)0.0002 (16)0.0002 (15)0.0006 (17)
C550.0286 (19)0.028 (2)0.038 (2)0.0032 (17)0.0022 (15)0.0007 (18)
C560.0318 (19)0.032 (2)0.035 (2)0.0012 (17)0.0039 (15)0.0021 (17)
C570.035 (2)0.025 (2)0.039 (2)0.0004 (17)0.0019 (16)0.0041 (17)
C580.0245 (18)0.0285 (19)0.037 (2)0.0046 (17)0.0008 (14)0.0025 (17)
C590.031 (2)0.032 (2)0.039 (2)0.0005 (18)0.0023 (15)0.0082 (18)
C600.0262 (19)0.034 (2)0.045 (2)0.0013 (17)0.0058 (16)0.0024 (19)
C610.0257 (18)0.030 (2)0.042 (2)0.0072 (17)0.0017 (15)0.0037 (18)
C620.0290 (19)0.036 (2)0.039 (2)0.0008 (18)0.0072 (15)0.0037 (18)
C630.0253 (18)0.032 (2)0.042 (2)0.0041 (17)0.0017 (15)0.0007 (18)
C640.033 (2)0.053 (3)0.038 (2)0.007 (2)0.0020 (16)0.019 (2)
C650.048 (3)0.077 (3)0.047 (3)0.021 (3)0.004 (2)0.015 (2)
C660.058 (3)0.071 (4)0.051 (3)0.035 (3)0.033 (2)0.023 (3)
C670.066 (3)0.054 (3)0.044 (3)0.009 (3)0.007 (2)0.004 (2)
C680.066 (3)0.056 (3)0.067 (3)0.002 (3)0.007 (2)0.024 (3)
C690.036 (2)0.054 (3)0.055 (3)0.010 (2)0.0128 (18)0.022 (2)
C700.116 (5)0.142 (7)0.092 (5)0.035 (5)0.023 (4)0.034 (5)
C710.030 (2)0.041 (2)0.039 (2)0.003 (2)0.0007 (16)0.003 (2)
C720.044 (2)0.037 (2)0.043 (2)0.009 (2)0.0027 (18)0.0002 (19)
C730.064 (3)0.052 (3)0.057 (3)0.024 (3)0.012 (2)0.011 (2)
C740.047 (3)0.101 (4)0.064 (3)0.029 (3)0.015 (2)0.041 (3)
C750.037 (2)0.111 (5)0.063 (3)0.011 (3)0.005 (2)0.043 (3)
C760.040 (2)0.081 (4)0.041 (2)0.014 (2)0.0056 (18)0.015 (2)
Geometric parameters (Å, º) top
N1—C81.419 (4)C32B—H32F0.9800
N1—C11.422 (4)C38—H380.9500
N1—C141.429 (4)N3—C521.415 (4)
N2—C331.420 (5)N3—C461.428 (4)
N2—C261.424 (4)N3—C391.430 (4)
N2—C231.428 (4)N4—C641.416 (4)
C1—C21.365 (5)N4—C611.417 (4)
C1—C61.403 (6)N4—C711.418 (4)
C2—C31.430 (6)C39—C441.375 (5)
C2—H20.9500C39—C401.385 (5)
C3—C41.367 (6)C40—C411.404 (5)
C3—C71.464 (6)C40—H400.9500
C4—C51.336 (6)C41—C421.383 (6)
C4—H40.9500C41—C451.488 (6)
C5—C61.385 (5)C42—C431.382 (6)
C5—H50.9500C42—H420.9500
C6—H60.9500C43—C441.382 (5)
C7—H7A0.9800C43—H430.9500
C7—H7B0.9800C44—H440.9500
C7—H7C0.9800C45—H45A0.9800
C8—C131.382 (5)C45—H45B0.9800
C8—C91.384 (5)C45—H45C0.9800
C9—C101.409 (5)C46—C471.379 (5)
C9—H90.9500C46—C511.385 (5)
C10—C111.358 (7)C47—C481.405 (5)
C10—H100.9500C47—H470.9500
C11—C121.401 (7)C48—C491.367 (5)
C11—H110.9500C48—H480.9500
C12—C131.405 (6)C49—C501.372 (6)
C12—H120.9500C49—H490.9500
C13—H130.9500C50—C511.381 (5)
C14—C191.383 (5)C50—H500.9500
C14—C151.393 (5)C51—H510.9500
C15—C161.398 (5)C52—C571.385 (5)
C15—H150.9500C52—C531.400 (5)
C16—C171.386 (5)C53—C541.376 (4)
C16—H160.9500C53—H530.9500
C17—C181.395 (5)C54—C551.396 (5)
C17—C201.487 (4)C54—H540.9500
C18—C191.377 (4)C55—C561.397 (5)
C18—H180.9500C55—C581.485 (4)
C19—H190.9500C56—C571.381 (4)
C20—C211.391 (5)C56—H560.9500
C20—C251.401 (5)C57—H570.9500
C21—C221.379 (5)C58—C591.385 (5)
C21—H210.9500C58—C631.405 (5)
C22—C231.396 (5)C59—C601.379 (4)
C22—H220.9500C59—H590.9500
C23—C241.399 (5)C60—C611.388 (5)
C24—C251.379 (4)C60—H600.9500
C24—H240.9500C61—C621.401 (5)
C25—H250.9500C62—C631.384 (4)
C26—C271.379 (5)C62—H620.9500
C26—C311.384 (5)C63—H630.9500
C27—C281.368 (6)C64—C651.359 (5)
C27—H270.9500C64—C691.404 (6)
C29—C301.358 (6)C65—C661.466 (6)
C29—C281.367 (6)C65—H650.9500
C29—H290.9500C66—C671.375 (6)
C30—C311.413 (5)C66—C701.429 (7)
C30—H300.9500C67—C681.312 (6)
C31—H310.9500C67—H670.9500
C33—C381.379 (5)C68—C691.391 (6)
C33—C341.379 (5)C68—H680.9500
C34—C351.369 (5)C69—H690.9500
C34—H340.9500C70—H70A0.9800
C35—C361.365 (6)C70—H70B0.9800
C35—H350.9500C70—H70C0.9800
C36—C371.388 (6)C71—C721.385 (5)
C36—H360.9500C71—C761.396 (5)
C37—C381.392 (5)C72—C731.412 (5)
C37—C32B1.467 (8)C72—H720.9500
C37—H370.9500C73—C741.371 (6)
C32A—C281.418 (11)C73—H730.9500
C32A—H32A0.9800C74—C751.384 (7)
C32A—H32B0.9800C74—H740.9500
C32A—H32C0.9800C75—C761.404 (6)
C28—H280.9500C75—H750.9500
C32B—H32D0.9800C76—H760.9500
C32B—H32E0.9800
C8—N1—C1120.4 (3)H32D—C32B—H32F109.5
C8—N1—C14120.3 (3)H32E—C32B—H32F109.5
C1—N1—C14118.2 (3)C33—C38—C37121.0 (4)
C33—N2—C26118.7 (3)C33—C38—H38119.5
C33—N2—C23119.8 (3)C37—C38—H38119.5
C26—N2—C23121.1 (3)C52—N3—C46122.0 (3)
C2—C1—C6118.9 (4)C52—N3—C39120.1 (3)
C2—C1—N1119.9 (4)C46—N3—C39117.7 (3)
C6—C1—N1121.2 (3)C64—N4—C61118.6 (3)
C1—C2—C3119.6 (4)C64—N4—C71120.6 (3)
C1—C2—H2120.2C61—N4—C71119.9 (3)
C3—C2—H2120.2C44—C39—C40120.6 (4)
C4—C3—C2118.4 (4)C44—C39—N3121.3 (3)
C4—C3—C7124.2 (4)C40—C39—N3118.1 (3)
C2—C3—C7117.3 (5)C39—C40—C41120.8 (4)
C5—C4—C3123.0 (4)C39—C40—H40119.6
C5—C4—H4118.5C41—C40—H40119.6
C3—C4—H4118.5C42—C41—C40117.5 (4)
C4—C5—C6118.9 (4)C42—C41—C45122.1 (4)
C4—C5—H5120.6C40—C41—C45120.4 (4)
C6—C5—H5120.6C43—C42—C41121.4 (4)
C5—C6—C1121.1 (4)C43—C42—H42119.3
C5—C6—H6119.4C41—C42—H42119.3
C1—C6—H6119.4C44—C43—C42120.4 (4)
C3—C7—H7A109.5C44—C43—H43119.8
C3—C7—H7B109.5C42—C43—H43119.8
H7A—C7—H7B109.5C39—C44—C43119.2 (4)
C3—C7—H7C109.5C39—C44—H44120.4
H7A—C7—H7C109.5C43—C44—H44120.4
H7B—C7—H7C109.5C41—C45—H45A109.5
C13—C8—C9120.1 (4)C41—C45—H45B109.5
C13—C8—N1120.6 (4)H45A—C45—H45B109.5
C9—C8—N1119.3 (3)C41—C45—H45C109.5
C8—C9—C10119.5 (4)H45A—C45—H45C109.5
C8—C9—H9120.3H45B—C45—H45C109.5
C10—C9—H9120.3C47—C46—C51119.0 (4)
C11—C10—C9121.1 (5)C47—C46—N3121.3 (3)
C11—C10—H10119.5C51—C46—N3119.7 (3)
C9—C10—H10119.5C46—C47—C48118.9 (4)
C10—C11—C12119.6 (4)C46—C47—H47120.6
C10—C11—H11120.2C48—C47—H47120.6
C12—C11—H11120.2C49—C48—C47120.9 (4)
C11—C12—C13119.8 (5)C49—C48—H48119.6
C11—C12—H12120.1C47—C48—H48119.6
C13—C12—H12120.1C48—C49—C50120.7 (4)
C8—C13—C12120.0 (5)C48—C49—H49119.7
C8—C13—H13120.0C50—C49—H49119.7
C12—C13—H13120.0C49—C50—C51118.5 (4)
C19—C14—C15118.7 (3)C49—C50—H50120.7
C19—C14—N1121.3 (3)C51—C50—H50120.7
C15—C14—N1120.0 (3)C50—C51—C46122.1 (4)
C14—C15—C16120.3 (3)C50—C51—H51119.0
C14—C15—H15119.8C46—C51—H51119.0
C16—C15—H15119.8C57—C52—C53117.6 (3)
C17—C16—C15121.2 (3)C57—C52—N3121.3 (3)
C17—C16—H16119.4C53—C52—N3121.1 (3)
C15—C16—H16119.4C54—C53—C52120.7 (3)
C16—C17—C18117.2 (3)C54—C53—H53119.6
C16—C17—C20122.0 (3)C52—C53—H53119.6
C18—C17—C20120.9 (3)C53—C54—C55122.1 (3)
C19—C18—C17122.2 (3)C53—C54—H54118.9
C19—C18—H18118.9C55—C54—H54118.9
C17—C18—H18118.9C54—C55—C56116.7 (3)
C18—C19—C14120.4 (3)C54—C55—C58121.6 (3)
C18—C19—H19119.8C56—C55—C58121.7 (3)
C14—C19—H19119.8C57—C56—C55121.4 (3)
C21—C20—C25117.0 (3)C57—C56—H56119.3
C21—C20—C17121.7 (3)C55—C56—H56119.3
C25—C20—C17121.3 (3)C56—C57—C52121.5 (3)
C22—C21—C20121.9 (3)C56—C57—H57119.3
C22—C21—H21119.1C52—C57—H57119.3
C20—C21—H21119.1C59—C58—C63117.0 (3)
C21—C22—C23120.7 (3)C59—C58—C55121.2 (3)
C21—C22—H22119.6C63—C58—C55121.7 (3)
C23—C22—H22119.6C60—C59—C58122.5 (3)
C22—C23—C24118.1 (3)C60—C59—H59118.7
C22—C23—N2120.9 (3)C58—C59—H59118.7
C24—C23—N2121.0 (3)C59—C60—C61120.4 (3)
C25—C24—C23120.5 (3)C59—C60—H60119.8
C25—C24—H24119.8C61—C60—H60119.8
C23—C24—H24119.8C60—C61—C62118.1 (3)
C24—C25—C20121.8 (3)C60—C61—N4121.2 (3)
C24—C25—H25119.1C62—C61—N4120.7 (3)
C20—C25—H25119.1C63—C62—C61121.0 (3)
C27—C26—C31119.7 (4)C63—C62—H62119.5
C27—C26—N2119.5 (3)C61—C62—H62119.5
C31—C26—N2120.8 (3)C62—C63—C58120.9 (3)
C28—C27—C26121.8 (4)C62—C63—H63119.5
C28—C27—H27119.1C58—C63—H63119.5
C26—C27—H27119.1C65—C64—C69119.5 (4)
C30—C29—C28120.9 (4)C65—C64—N4120.2 (4)
C30—C29—H29119.6C69—C64—N4120.4 (4)
C28—C29—H29119.6C64—C65—C66117.7 (4)
C29—C30—C31120.9 (4)C64—C65—H65121.1
C29—C30—H30119.6C66—C65—H65121.1
C31—C30—H30119.6C67—C66—C70124.4 (5)
C26—C31—C30117.8 (4)C67—C66—C65118.6 (4)
C26—C31—H31121.1C70—C66—C65116.9 (5)
C30—C31—H31121.1C68—C67—C66123.9 (5)
C38—C33—C34119.5 (4)C68—C67—H67118.0
C38—C33—N2118.9 (3)C66—C67—H67118.0
C34—C33—N2121.7 (3)C67—C68—C69117.9 (5)
C35—C34—C33120.3 (4)C67—C68—H68121.0
C35—C34—H34119.9C69—C68—H68121.0
C33—C34—H34119.9C68—C69—C64122.4 (4)
C36—C35—C34120.1 (4)C68—C69—H69118.8
C36—C35—H35120.0C64—C69—H69118.8
C34—C35—H35120.0C66—C70—H70A109.5
C35—C36—C37121.4 (4)C66—C70—H70B109.5
C35—C36—H36119.3H70A—C70—H70B109.5
C37—C36—H36119.3C66—C70—H70C109.5
C36—C37—C38117.7 (4)H70A—C70—H70C109.5
C36—C37—C32B121.8 (5)H70B—C70—H70C109.5
C38—C37—C32B120.2 (5)C72—C71—C76119.1 (3)
C36—C37—H37121.1C72—C71—N4120.0 (3)
C38—C37—H37121.1C76—C71—N4120.9 (3)
C28—C32A—H32A109.5C71—C72—C73120.1 (4)
C28—C32A—H32B109.5C71—C72—H72120.0
H32A—C32A—H32B109.5C73—C72—H72120.0
C28—C32A—H32C109.5C74—C73—C72120.2 (4)
H32A—C32A—H32C109.5C74—C73—H73119.9
H32B—C32A—H32C109.5C72—C73—H73119.9
C29—C28—C27118.9 (4)C73—C74—C75120.5 (4)
C29—C28—C32A106.4 (6)C73—C74—H74119.8
C27—C28—C32A134.6 (7)C75—C74—H74119.8
C29—C28—H28120.5C74—C75—C76119.6 (4)
C27—C28—H28120.5C74—C75—H75120.2
C37—C32B—H32D109.5C76—C75—H75120.2
C37—C32B—H32E109.5C71—C76—C75120.5 (4)
H32D—C32B—H32E109.5C71—C76—H76119.7
C37—C32B—H32F109.5C75—C76—H76119.7
C8—N1—C1—C2138.0 (4)C32B—C37—C38—C33174.2 (5)
C14—N1—C1—C254.0 (5)C52—N3—C39—C4455.9 (5)
C8—N1—C1—C640.5 (5)C46—N3—C39—C44129.3 (4)
C14—N1—C1—C6127.5 (4)C52—N3—C39—C40124.3 (4)
C6—C1—C2—C31.7 (6)C46—N3—C39—C4050.5 (5)
N1—C1—C2—C3179.8 (3)C44—C39—C40—C410.9 (6)
C1—C2—C3—C40.1 (6)N3—C39—C40—C41179.4 (3)
C1—C2—C3—C7176.7 (4)C39—C40—C41—C420.0 (6)
C2—C3—C4—C51.8 (6)C39—C40—C41—C45177.2 (4)
C7—C3—C4—C5174.8 (5)C40—C41—C42—C430.6 (6)
C3—C4—C5—C61.4 (6)C45—C41—C42—C43177.8 (4)
C4—C5—C6—C10.5 (6)C41—C42—C43—C440.4 (6)
C2—C1—C6—C52.0 (6)C40—C39—C44—C431.1 (6)
N1—C1—C6—C5179.4 (3)N3—C39—C44—C43179.2 (3)
C1—N1—C8—C13136.4 (4)C42—C43—C44—C390.5 (6)
C14—N1—C8—C1331.4 (6)C52—N3—C46—C4744.0 (5)
C1—N1—C8—C945.5 (5)C39—N3—C46—C47130.6 (3)
C14—N1—C8—C9146.8 (4)C52—N3—C46—C51137.7 (3)
C13—C8—C9—C101.2 (6)C39—N3—C46—C5147.6 (5)
N1—C8—C9—C10177.0 (4)C51—C46—C47—C481.4 (5)
C8—C9—C10—C110.5 (6)N3—C46—C47—C48179.6 (3)
C9—C10—C11—C122.2 (7)C46—C47—C48—C491.0 (5)
C10—C11—C12—C132.1 (7)C47—C48—C49—C500.1 (6)
C9—C8—C13—C121.3 (7)C48—C49—C50—C510.9 (6)
N1—C8—C13—C12176.9 (4)C49—C50—C51—C460.5 (6)
C11—C12—C13—C80.3 (7)C47—C46—C51—C500.6 (6)
C8—N1—C14—C19136.3 (4)N3—C46—C51—C50178.9 (3)
C1—N1—C14—C1931.7 (5)C46—N3—C52—C57155.2 (3)
C8—N1—C14—C1544.8 (5)C39—N3—C52—C5719.4 (5)
C1—N1—C14—C15147.2 (4)C46—N3—C52—C5326.0 (5)
C19—C14—C15—C160.3 (5)C39—N3—C52—C53159.4 (3)
N1—C14—C15—C16178.6 (3)C57—C52—C53—C540.9 (5)
C14—C15—C16—C170.3 (5)N3—C52—C53—C54177.9 (3)
C15—C16—C17—C180.5 (5)C52—C53—C54—C550.3 (5)
C15—C16—C17—C20178.5 (3)C53—C54—C55—C560.4 (5)
C16—C17—C18—C191.4 (5)C53—C54—C55—C58177.5 (3)
C20—C17—C18—C19177.7 (3)C54—C55—C56—C570.4 (5)
C17—C18—C19—C141.4 (5)C58—C55—C56—C57177.5 (3)
C15—C14—C19—C180.5 (5)C55—C56—C57—C520.3 (5)
N1—C14—C19—C18179.4 (3)C53—C52—C57—C560.9 (5)
C16—C17—C20—C2136.5 (5)N3—C52—C57—C56177.9 (3)
C18—C17—C20—C21142.5 (4)C54—C55—C58—C5935.7 (5)
C16—C17—C20—C25144.8 (3)C56—C55—C58—C59142.1 (4)
C18—C17—C20—C2536.2 (5)C54—C55—C58—C63145.8 (3)
C25—C20—C21—C220.2 (5)C56—C55—C58—C6336.4 (5)
C17—C20—C21—C22178.5 (3)C63—C58—C59—C600.3 (5)
C20—C21—C22—C230.1 (5)C55—C58—C59—C60178.3 (3)
C21—C22—C23—C240.2 (5)C58—C59—C60—C610.2 (5)
C21—C22—C23—N2178.3 (3)C59—C60—C61—C620.5 (5)
C33—N2—C23—C2219.0 (5)C59—C60—C61—N4179.2 (3)
C26—N2—C23—C22154.3 (3)C64—N4—C61—C6034.4 (5)
C33—N2—C23—C24159.4 (3)C71—N4—C61—C60135.0 (4)
C26—N2—C23—C2427.3 (5)C64—N4—C61—C62145.4 (4)
C22—C23—C24—C250.1 (5)C71—N4—C61—C6245.2 (5)
N2—C23—C24—C25178.5 (3)C60—C61—C62—C630.4 (5)
C23—C24—C25—C200.4 (5)N4—C61—C62—C63179.4 (3)
C21—C20—C25—C240.5 (5)C61—C62—C63—C580.1 (5)
C17—C20—C25—C24178.2 (3)C59—C58—C63—C620.5 (5)
C33—N2—C26—C2747.7 (5)C55—C58—C63—C62178.1 (3)
C23—N2—C26—C27138.9 (3)C61—N4—C64—C6552.9 (5)
C33—N2—C26—C31130.2 (4)C71—N4—C64—C65137.8 (4)
C23—N2—C26—C3143.2 (5)C61—N4—C64—C69127.0 (4)
C31—C26—C27—C281.7 (6)C71—N4—C64—C6942.3 (5)
N2—C26—C27—C28179.6 (3)C69—C64—C65—C660.5 (6)
C28—C29—C30—C310.3 (6)N4—C64—C65—C66179.3 (3)
C27—C26—C31—C302.4 (5)C64—C65—C66—C670.5 (6)
N2—C26—C31—C30179.7 (3)C64—C65—C66—C70176.3 (5)
C29—C30—C31—C261.7 (5)C70—C66—C67—C68175.5 (5)
C26—N2—C33—C3849.6 (5)C65—C66—C67—C681.0 (6)
C23—N2—C33—C38123.9 (4)C66—C67—C68—C690.4 (7)
C26—N2—C33—C34129.5 (4)C67—C68—C69—C640.7 (6)
C23—N2—C33—C3457.1 (5)C65—C64—C69—C681.2 (6)
C38—C33—C34—C351.1 (6)N4—C64—C69—C68178.7 (4)
N2—C33—C34—C35179.8 (4)C64—N4—C71—C7243.5 (5)
C33—C34—C35—C360.0 (6)C61—N4—C71—C72147.3 (4)
C34—C35—C36—C371.4 (7)C64—N4—C71—C76136.5 (4)
C35—C36—C37—C381.6 (7)C61—N4—C71—C7632.6 (6)
C35—C36—C37—C32B175.3 (5)C76—C71—C72—C732.0 (6)
C30—C29—C28—C270.5 (6)N4—C71—C72—C73178.0 (4)
C30—C29—C28—C32A176.6 (7)C71—C72—C73—C740.4 (6)
C26—C27—C28—C290.2 (6)C72—C73—C74—C751.3 (7)
C26—C27—C28—C32A176.2 (8)C73—C74—C75—C761.4 (7)
C34—C33—C38—C371.0 (6)C72—C71—C76—C751.8 (6)
N2—C33—C38—C37180.0 (4)N4—C71—C76—C75178.1 (4)
C36—C37—C38—C330.4 (6)C74—C75—C76—C710.1 (7)

Experimental details

Crystal data
Chemical formulaC38H32N2
Mr516.66
Crystal system, space groupMonoclinic, P21
Temperature (K)90
a, b, c (Å)14.447 (2), 11.0153 (16), 17.803 (3)
β (°) 90.602 (3)
V3)2833.0 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerPlateform with APEX CCD detector
diffractometer
Absorption correctionMulti-scan
(TWINABS in SAINT-Plus; Sheldrick, 1999)
Tmin, Tmax0.971, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
10070, 10070, 4919
Rint0.000
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.130, 0.90
No. of reflections10070
No. of parameters735
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPIII for Windows (Farrugia, 1997), SHELXL97 and local programs.

Selected geometric parameters (Å, º) top
N1—C81.419 (4)N3—C521.415 (4)
N1—C11.422 (4)N3—C461.428 (4)
N1—C141.429 (4)N3—C391.430 (4)
N2—C331.420 (5)N4—C641.416 (4)
N2—C261.424 (4)N4—C611.417 (4)
N2—C231.428 (4)N4—C711.418 (4)
C17—C201.487 (4)C55—C581.485 (4)
C8—N1—C1120.4 (3)C52—N3—C46122.0 (3)
C8—N1—C14120.3 (3)C52—N3—C39120.1 (3)
C1—N1—C14118.2 (3)C46—N3—C39117.7 (3)
C33—N2—C26118.7 (3)C64—N4—C61118.6 (3)
C33—N2—C23119.8 (3)C64—N4—C71120.6 (3)
C26—N2—C23121.1 (3)C61—N4—C71119.9 (3)
C14—N1—C1—C254.0 (5)C52—N3—C39—C4455.9 (5)
C8—N1—C1—C640.5 (5)C46—N3—C39—C4050.5 (5)
C14—N1—C8—C1331.4 (6)C52—N3—C46—C4744.0 (5)
C1—N1—C8—C945.5 (5)C39—N3—C46—C5147.6 (5)
C1—N1—C14—C1931.7 (5)C39—N3—C52—C5719.4 (5)
C8—N1—C14—C1544.8 (5)C46—N3—C52—C5326.0 (5)
C16—C17—C20—C2136.5 (5)C54—C55—C58—C5935.7 (5)
C18—C17—C20—C2536.2 (5)C56—C55—C58—C6336.4 (5)
C33—N2—C23—C2219.0 (5)C64—N4—C61—C6034.4 (5)
C26—N2—C23—C2427.3 (5)C71—N4—C61—C6245.2 (5)
C33—N2—C26—C2747.7 (5)C61—N4—C64—C6552.9 (5)
C23—N2—C26—C3143.2 (5)C71—N4—C64—C6942.3 (5)
C26—N2—C33—C3849.6 (5)C64—N4—C71—C7243.5 (5)
C23—N2—C33—C3457.1 (5)C61—N4—C71—C7632.6 (6)
 

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