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The title compound, C35H54N2, crystallizes as the E/Z and E/E isomers. There are two independent mol­ecules in the crystal; the first occupies a general position, adopts a non-symmetrical conformation and represents the E/Z isomer with respect to the C=N bonds; the second exhibits exact C2 symmetry (E/E isomer). The observed bond lengths and disposition of the H atoms in both mol­ecules are consistent with a di­imine. This contrasts with the related compound 2-(2,6-diiso­propylphenyl­amino)-4-(2,6-diiso­propyl­phenyl­imino)-2-pentene, which crystallizes as the imine-en­amine tautomer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011783/ya6044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011783/ya6044Isup2.hkl
Contains datablock I

CCDC reference: 172214

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.124
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Diimine ligands such as the title compound, (1), have attracted attention as useful and versatile sources of monoanionic ligands for early transition metals in olefin polymerization (Budzelaar et al., 1998). Recently, we have been interested in the application of (1) for olefin polymerization by nitrogen ligated organomagnesium species (Bailey, Coxall et al., 2001). However, whilst there are now a growing number of metal complexes involving this ligand in the deprotonated monoanionic form as chelates, there are no examples to date of the free protonated parent 1,3-diimine ligand (1) with the intact C—NC(R)—CH2—C(R)N—C chain. Following on from our earlier report of the closely related β-diketimine compound (2) (Bailey, Liddle & Parsons, 2001), we report here the crystal structure of (1), which was synthesized via a coupling–elimination reaction of 1-chloro-1-(2,6-diisopropylphenylimino)-2,2-dimethylpropane and lithium-2-(2,6-diisopropylphenylimino)-3,3-dimethylbutane (Knorr & Weiss., 1982).

The crystal structure is composed of discrete molecules of (1) exhibiting no significant intermolecular contacts. There are two independent molecules in the crystal; the first occupies a general position and adopts a non-symmetrical conformation (Fig. 1), the second exhibits exact C2 symmetry (Fig. 2). Examination of bond lengths and the disposition of the H atoms within the N—C—C—C—N backbones of both independent molecules (Table 1) reveals that (1) crystallizes as the diimine tautomer. This contrasts with (2), which crystallizes as the imine–enamine tautomer.

In the crystal examined, the two independent molecules exhibit different isomeric forms with respect to the CN bonds; the non-symmetrical conformer adopts the E/Z form, whereas the C2 conformer adopts the E/E form. In both independent molecules, the tert-butyl groups (C1, C8 and C36) adopt an anti orientation with respect to each other; this is clearly a result of the steric bulk of the tert-butyl groups, as the equivalent methyl groups in (2) adopt a syn conformation in the solid state.

Experimental top

Compound (1) was synthesized by a coupling reaction of 1-chloro-1-(2,6-diisopropylphenylimino)-2,2-dimethylpropane and 1-lithium-2-(2,6-diisopropylphenylimino)-3,3-dimethylbutane (Knorr & Weiss, 1982). Crystals were obtained from a saturated solution in hexane at 243 K.

Refinement top

Analysis of Fourier difference maps, based on the refinement of non-H atoms, clearly showed the location of the H atoms at C6 (two H atoms) and C41 (one idependent H atom). No peaks corresponding to H atoms in the vicinity of N atoms N1, N2 or N3 were observed. After inspection of the difference map, all H atoms were placed in calculated positions and subsequently allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). Methyl groups were treated as rotating rigid groups with Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the non-symmetrical conformer of (1) with the atom-numbering scheme. Displacement ellipsoids enclose 30% probability surfaces.
[Figure 2] Fig. 2. A view of the C2-symmetric conformer of (1) with a selected atom-numbering scheme. Displacement ellipsoids enclose 30% probability surfaces.
2,2,6,6-Tetramethyl-3,5-di(2,6-diisopropylphenylimino)heptane top
Crystal data top
C35H54N2F(000) = 3336
Mr = 502.80Dx = 1.058 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 41.471 (4) ÅCell parameters from 7323 reflections
b = 9.3431 (9) Åθ = 2.2–26.3°
c = 24.989 (3) ŵ = 0.06 mm1
β = 102.077 (2)°T = 150 K
V = 9468.0 (16) Å3Block, colourless
Z = 120.42 × 0.26 × 0.19 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8317 independent reflections
Radiation source: fine-focus sealed tube5827 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 4949
Tmin = 0.975, Tmax = 0.989k = 1111
33069 measured reflectionsl = 2929
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0566P)2 + 4.2336P]
where P = (Fo2 + 2Fc2)/3
8317 reflections(Δ/σ)max < 0.001
501 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C35H54N2V = 9468.0 (16) Å3
Mr = 502.80Z = 12
Monoclinic, C2/cMo Kα radiation
a = 41.471 (4) ŵ = 0.06 mm1
b = 9.3431 (9) ÅT = 150 K
c = 24.989 (3) Å0.42 × 0.26 × 0.19 mm
β = 102.077 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8317 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
5827 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.989Rint = 0.043
33069 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.02Δρmax = 0.49 e Å3
8317 reflectionsΔρmin = 0.25 e Å3
501 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)
N10.20403 (3)0.83135 (15)0.09213 (6)0.0248 (3)
N20.12744 (4)0.79900 (17)0.03313 (6)0.0316 (4)
C10.16297 (4)0.87388 (19)0.15363 (7)0.0263 (4)
C20.18945 (5)0.8527 (2)0.20558 (7)0.0383 (5)
H2B0.17930.85590.23760.057*
H2C0.20590.92900.20840.057*
H2D0.20020.75970.20410.057*
C30.13716 (5)0.7545 (2)0.15055 (8)0.0374 (5)
H3A0.12850.75460.18410.056*
H3B0.14750.66170.14660.056*
H3C0.11910.77090.11890.056*
C40.14686 (5)1.0197 (2)0.15943 (8)0.0364 (5)
H4A0.13851.02130.19330.055*
H4B0.12861.03510.12810.055*
H4C0.16321.09590.16050.055*
C50.17610 (4)0.87051 (18)0.10016 (7)0.0240 (4)
C60.15109 (4)0.9287 (2)0.05112 (7)0.0359 (5)
H6A0.12880.91090.05830.043*
H6B0.15401.03390.05070.043*
C70.15099 (4)0.87509 (19)0.00586 (7)0.0248 (4)
C80.17728 (4)0.9244 (2)0.03722 (7)0.0286 (4)
C90.20138 (5)0.8010 (2)0.03904 (8)0.0363 (5)
H9A0.18920.71710.05600.055*
H9B0.21290.77720.00170.055*
H9C0.21750.82990.06060.055*
C100.19574 (5)1.0566 (2)0.01127 (8)0.0396 (5)
H10A0.18001.13450.01050.059*
H10B0.21181.08620.03280.059*
H10C0.20731.03410.02620.059*
C110.16028 (5)0.9624 (2)0.09604 (8)0.0437 (5)
H11A0.14820.87890.11350.066*
H11B0.17690.99080.11660.066*
H11C0.14491.04180.09560.066*
C120.23179 (4)0.78032 (18)0.13089 (7)0.0241 (4)
C130.25773 (4)0.87647 (19)0.15185 (7)0.0257 (4)
C140.28565 (4)0.8226 (2)0.18620 (7)0.0316 (4)
H14A0.30300.88640.20130.038*
C150.28911 (5)0.6788 (2)0.19919 (8)0.0335 (5)
H15A0.30850.64450.22310.040*
C160.26406 (4)0.5859 (2)0.17699 (7)0.0319 (4)
H16A0.26650.48680.18550.038*
C170.23520 (4)0.63329 (19)0.14240 (7)0.0263 (4)
C180.25620 (4)1.03292 (19)0.13577 (7)0.0293 (4)
H18A0.23251.05890.12210.035*
C190.27030 (5)1.1322 (2)0.18343 (9)0.0441 (5)
H19A0.25851.11730.21310.066*
H19B0.26771.23190.17110.066*
H19C0.29381.11110.19670.066*
C200.27432 (5)1.0558 (2)0.08906 (9)0.0431 (5)
H20A0.26510.99190.05860.065*
H20B0.29781.03470.10200.065*
H20C0.27171.15540.07670.065*
C210.20890 (4)0.52544 (19)0.11730 (7)0.0299 (4)
H21A0.18850.57980.10060.036*
C220.20019 (5)0.4229 (2)0.16012 (8)0.0395 (5)
H22A0.19280.47820.18870.059*
H22B0.21970.36660.17650.059*
H22C0.18250.35850.14250.059*
C230.22010 (5)0.4433 (2)0.07154 (9)0.0427 (5)
H23A0.22530.51110.04460.064*
H23B0.20240.37900.05370.064*
H23C0.23980.38700.08700.064*
C240.09973 (5)0.7528 (2)0.01259 (7)0.0322 (4)
C250.09847 (5)0.6100 (2)0.00478 (7)0.0329 (4)
C260.07011 (5)0.5651 (2)0.02182 (8)0.0380 (5)
H26A0.06890.47000.03470.046*
C270.04381 (5)0.6559 (2)0.02033 (8)0.0424 (5)
H27A0.02470.62310.03190.051*
C280.04516 (5)0.7945 (2)0.00200 (8)0.0407 (5)
H28A0.02670.85580.00080.049*
C290.07286 (5)0.8467 (2)0.01480 (8)0.0346 (5)
C300.12693 (5)0.5091 (2)0.00371 (8)0.0359 (5)
H30A0.14780.56360.01720.043*
C310.12755 (5)0.3789 (2)0.04053 (9)0.0489 (6)
H31A0.12790.41040.07800.073*
H31B0.14730.32190.04000.073*
H31C0.10790.32050.02730.073*
C320.12696 (6)0.4610 (2)0.05500 (9)0.0487 (6)
H32A0.12700.54530.07830.073*
H32B0.10720.40350.06900.073*
H32C0.14670.40340.05520.073*
C330.07342 (5)0.9974 (2)0.03751 (8)0.0381 (5)
H33A0.09661.03290.02690.046*
C340.05168 (6)1.1039 (3)0.01514 (10)0.0554 (6)
H34A0.05771.10420.02490.083*
H34B0.02851.07600.02700.083*
H34C0.05491.19980.02900.083*
C350.06415 (6)0.9949 (3)0.10001 (9)0.0546 (6)
H35A0.07840.92680.11400.082*
H35B0.06711.09070.11430.082*
H35C0.04110.96560.11180.082*
N30.04350 (3)0.56371 (15)0.19867 (6)0.0265 (3)
C360.00924 (4)0.4675 (2)0.15912 (8)0.0327 (4)
C370.01013 (5)0.3793 (2)0.12533 (8)0.0393 (5)
H37A0.02260.30490.14840.059*
H37B0.02540.44180.11110.059*
H37C0.00520.33450.09470.059*
C380.02884 (6)0.5824 (3)0.12150 (11)0.0678 (8)
H38A0.04150.64060.14250.102*
H38B0.04400.53570.09110.102*
H38C0.01350.64380.10700.102*
C390.03273 (6)0.3701 (3)0.18060 (11)0.0650 (8)
H39A0.02010.29750.20460.097*
H39B0.04740.32290.14980.097*
H39C0.04590.42660.20130.097*
C400.01407 (4)0.54663 (18)0.20530 (7)0.0248 (4)
C410.00000.6200 (3)0.25000.0314 (6)
H41A0.01770.68370.23060.038*0.50
H41B0.01770.68370.26940.038*0.50
C420.06920 (4)0.63572 (19)0.23488 (7)0.0261 (4)
C430.09599 (4)0.5499 (2)0.26040 (7)0.0285 (4)
C440.12235 (5)0.6153 (2)0.29493 (8)0.0347 (5)
H44A0.14020.55840.31350.042*
C450.12310 (5)0.7610 (2)0.30284 (8)0.0404 (5)
H45A0.14120.80380.32730.048*
C460.09755 (5)0.8452 (2)0.27521 (8)0.0373 (5)
H46A0.09860.94600.28030.045*
C470.07020 (4)0.7857 (2)0.24004 (7)0.0297 (4)
C480.09675 (4)0.3918 (2)0.24642 (8)0.0329 (4)
H48A0.07350.35670.23860.040*
C490.11621 (5)0.2993 (2)0.29231 (10)0.0505 (6)
H49A0.10730.31190.32540.076*
H49B0.13940.32800.29980.076*
H49C0.11430.19850.28120.076*
C500.10978 (6)0.3750 (2)0.19376 (10)0.0526 (6)
H50A0.09690.43540.16500.079*
H50B0.10780.27470.18200.079*
H50C0.13300.40410.20050.079*
C510.04393 (5)0.8799 (2)0.20547 (8)0.0353 (5)
H51A0.02240.82900.20170.042*
C520.04028 (8)1.0244 (3)0.23072 (12)0.0858 (10)
H52A0.03591.01120.26750.129*
H52B0.02191.07630.20790.129*
H52C0.06071.07930.23320.129*
C530.05044 (6)0.8985 (3)0.14854 (10)0.0715 (8)
H53A0.03320.95900.12690.107*
H53B0.05030.80460.13100.107*
H53C0.07200.94380.15090.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0264 (8)0.0244 (8)0.0237 (8)0.0015 (6)0.0054 (6)0.0006 (6)
N20.0335 (9)0.0338 (9)0.0293 (9)0.0027 (7)0.0109 (7)0.0030 (7)
C10.0282 (9)0.0281 (10)0.0233 (10)0.0020 (8)0.0071 (7)0.0016 (8)
C20.0397 (11)0.0553 (14)0.0216 (10)0.0108 (10)0.0105 (8)0.0009 (9)
C30.0436 (12)0.0366 (11)0.0385 (12)0.0034 (9)0.0233 (10)0.0030 (9)
C40.0387 (11)0.0339 (11)0.0383 (12)0.0050 (9)0.0122 (9)0.0011 (9)
C50.0248 (9)0.0222 (9)0.0247 (10)0.0040 (7)0.0043 (7)0.0003 (7)
C60.0252 (10)0.0547 (13)0.0287 (10)0.0006 (9)0.0075 (8)0.0030 (9)
C70.0255 (9)0.0243 (9)0.0244 (10)0.0081 (8)0.0048 (7)0.0033 (7)
C80.0287 (10)0.0316 (10)0.0264 (10)0.0028 (8)0.0081 (8)0.0037 (8)
C90.0362 (11)0.0405 (12)0.0368 (11)0.0047 (9)0.0178 (9)0.0011 (9)
C100.0398 (11)0.0377 (12)0.0446 (12)0.0035 (9)0.0164 (10)0.0013 (9)
C110.0427 (12)0.0589 (14)0.0326 (11)0.0032 (11)0.0146 (9)0.0140 (10)
C120.0263 (9)0.0294 (10)0.0183 (9)0.0035 (8)0.0087 (7)0.0002 (7)
C130.0273 (9)0.0280 (10)0.0234 (9)0.0026 (8)0.0090 (7)0.0022 (8)
C140.0278 (10)0.0360 (11)0.0300 (11)0.0012 (8)0.0038 (8)0.0043 (8)
C150.0294 (10)0.0361 (11)0.0330 (11)0.0068 (9)0.0021 (8)0.0050 (9)
C160.0355 (11)0.0274 (10)0.0339 (11)0.0054 (9)0.0099 (9)0.0047 (8)
C170.0282 (10)0.0278 (10)0.0249 (10)0.0017 (8)0.0102 (8)0.0012 (8)
C180.0274 (10)0.0270 (10)0.0331 (11)0.0008 (8)0.0052 (8)0.0021 (8)
C190.0465 (12)0.0320 (12)0.0497 (13)0.0030 (10)0.0008 (10)0.0085 (10)
C200.0494 (13)0.0318 (12)0.0530 (14)0.0055 (10)0.0217 (11)0.0075 (10)
C210.0313 (10)0.0273 (10)0.0323 (11)0.0027 (8)0.0095 (8)0.0030 (8)
C220.0373 (11)0.0363 (12)0.0466 (13)0.0014 (9)0.0122 (9)0.0074 (9)
C230.0464 (12)0.0378 (12)0.0474 (13)0.0058 (10)0.0174 (10)0.0104 (10)
C240.0341 (11)0.0396 (12)0.0242 (10)0.0046 (9)0.0091 (8)0.0068 (8)
C250.0340 (11)0.0404 (12)0.0235 (10)0.0055 (9)0.0044 (8)0.0038 (8)
C260.0410 (12)0.0437 (12)0.0295 (11)0.0087 (10)0.0079 (9)0.0011 (9)
C270.0380 (12)0.0561 (15)0.0364 (12)0.0091 (10)0.0151 (9)0.0032 (10)
C280.0355 (11)0.0511 (14)0.0372 (12)0.0023 (10)0.0111 (9)0.0063 (10)
C290.0351 (11)0.0413 (12)0.0278 (11)0.0031 (9)0.0075 (8)0.0050 (9)
C300.0349 (11)0.0359 (11)0.0355 (11)0.0044 (9)0.0039 (9)0.0014 (9)
C310.0457 (13)0.0458 (13)0.0532 (14)0.0012 (11)0.0057 (11)0.0060 (11)
C320.0531 (14)0.0512 (14)0.0426 (13)0.0105 (11)0.0116 (11)0.0052 (10)
C330.0357 (11)0.0406 (12)0.0371 (12)0.0021 (9)0.0060 (9)0.0025 (9)
C340.0532 (14)0.0480 (14)0.0665 (16)0.0054 (11)0.0161 (12)0.0054 (12)
C350.0687 (16)0.0503 (14)0.0425 (14)0.0000 (12)0.0061 (12)0.0023 (11)
N30.0267 (8)0.0247 (8)0.0293 (8)0.0005 (6)0.0088 (7)0.0011 (6)
C360.0265 (10)0.0311 (11)0.0397 (11)0.0005 (8)0.0050 (8)0.0036 (9)
C370.0393 (11)0.0452 (13)0.0323 (11)0.0050 (10)0.0052 (9)0.0099 (9)
C380.0625 (16)0.0556 (16)0.0671 (17)0.0167 (13)0.0278 (13)0.0115 (13)
C390.0613 (15)0.0655 (17)0.0790 (18)0.0355 (13)0.0396 (14)0.0366 (14)
C400.0275 (10)0.0200 (9)0.0287 (10)0.0040 (7)0.0097 (8)0.0053 (7)
C410.0321 (14)0.0248 (14)0.0403 (16)0.0000.0147 (12)0.000
C420.0271 (9)0.0283 (10)0.0262 (10)0.0027 (8)0.0129 (8)0.0053 (8)
C430.0260 (9)0.0308 (10)0.0320 (10)0.0028 (8)0.0133 (8)0.0018 (8)
C440.0295 (10)0.0415 (12)0.0338 (11)0.0009 (9)0.0081 (8)0.0021 (9)
C450.0381 (12)0.0481 (13)0.0347 (12)0.0105 (10)0.0071 (9)0.0129 (10)
C460.0475 (12)0.0272 (11)0.0419 (12)0.0099 (9)0.0204 (10)0.0117 (9)
C470.0340 (10)0.0285 (10)0.0310 (10)0.0021 (8)0.0171 (8)0.0032 (8)
C480.0242 (10)0.0290 (11)0.0475 (12)0.0009 (8)0.0118 (9)0.0003 (9)
C490.0361 (12)0.0381 (13)0.0748 (16)0.0017 (10)0.0058 (11)0.0065 (11)
C500.0609 (15)0.0349 (12)0.0726 (17)0.0046 (11)0.0384 (13)0.0097 (11)
C510.0381 (11)0.0263 (10)0.0454 (12)0.0002 (9)0.0176 (9)0.0016 (9)
C520.120 (3)0.0432 (16)0.082 (2)0.0374 (16)0.0071 (18)0.0103 (14)
C530.0538 (15)0.115 (2)0.0479 (15)0.0253 (16)0.0152 (12)0.0267 (15)
Geometric parameters (Å, º) top
N1—C51.270 (2)C27—H27A0.9500
N1—C121.423 (2)C28—C291.391 (3)
N2—C71.283 (2)C28—H28A0.9500
N2—C241.420 (2)C29—C331.521 (3)
C1—C21.528 (2)C30—C311.522 (3)
C1—C31.537 (3)C30—C321.535 (3)
C1—C41.538 (2)C30—H30A1.0000
C1—C51.545 (2)C31—H31A0.9800
C2—H2B0.9800C31—H31B0.9800
C2—H2C0.9800C31—H31C0.9800
C2—H2D0.9800C32—H32A0.9800
C3—H3A0.9800C32—H32B0.9800
C3—H3B0.9800C32—H32C0.9800
C3—H3C0.9800C33—C341.525 (3)
C4—H4A0.9800C33—C351.528 (3)
C4—H4B0.9800C33—H33A1.0000
C4—H4C0.9800C34—H34A0.9800
C5—C61.530 (2)C34—H34B0.9800
C6—C71.509 (3)C34—H34C0.9800
C6—H6A0.9900C35—H35A0.9800
C6—H6B0.9900C35—H35B0.9800
C7—C81.540 (2)C35—H35C0.9800
C8—C101.525 (3)N3—C401.275 (2)
C8—C91.533 (3)N3—C421.416 (2)
C8—C111.533 (3)C36—C391.512 (3)
C9—H9A0.9800C36—C371.524 (3)
C9—H9B0.9800C36—C401.531 (3)
C9—H9C0.9800C36—C381.541 (3)
C10—H10A0.9800C37—H37A0.9800
C10—H10B0.9800C37—H37B0.9800
C10—H10C0.9800C37—H37C0.9800
C11—H11A0.9800C38—H38A0.9800
C11—H11B0.9800C38—H38B0.9800
C11—H11C0.9800C38—H38C0.9800
C12—C171.405 (2)C39—H39A0.9800
C12—C131.415 (2)C39—H39B0.9800
C13—C141.384 (2)C39—H39C0.9800
C13—C181.514 (2)C40—C411.527 (2)
C14—C151.383 (3)C41—C40i1.527 (2)
C14—H14A0.9500C41—H41A0.9900
C15—C161.378 (3)C41—H41B0.9900
C15—H15A0.9500C42—C471.407 (3)
C16—C171.394 (2)C42—C431.410 (3)
C16—H16A0.9500C43—C441.385 (3)
C17—C211.520 (2)C43—C481.520 (3)
C18—C191.526 (3)C44—C451.375 (3)
C18—C201.529 (3)C44—H44A0.9500
C18—H18A1.0000C45—C461.383 (3)
C19—H19A0.9800C45—H45A0.9500
C19—H19B0.9800C46—C471.397 (3)
C19—H19C0.9800C46—H46A0.9500
C20—H20A0.9800C47—C511.522 (3)
C20—H20B0.9800C48—C491.525 (3)
C20—H20C0.9800C48—C501.532 (3)
C21—C231.528 (3)C48—H48A1.0000
C21—C221.534 (3)C49—H49A0.9800
C21—H21A1.0000C49—H49B0.9800
C22—H22A0.9800C49—H49C0.9800
C22—H22B0.9800C50—H50A0.9800
C22—H22C0.9800C50—H50B0.9800
C23—H23A0.9800C50—H50C0.9800
C23—H23B0.9800C51—C521.510 (3)
C23—H23C0.9800C51—C531.512 (3)
C24—C251.408 (3)C51—H51A1.0000
C24—C291.410 (3)C52—H52A0.9800
C25—C261.396 (3)C52—H52B0.9800
C25—C301.515 (3)C52—H52C0.9800
C26—C271.376 (3)C53—H53A0.9800
C26—H26A0.9500C53—H53B0.9800
C27—C281.378 (3)C53—H53C0.9800
C5—N1—C12128.60 (15)C27—C28—H28A119.2
C7—N2—C24124.08 (15)C29—C28—H28A119.2
C2—C1—C3108.55 (16)C28—C29—C24117.78 (19)
C2—C1—C4106.49 (15)C28—C29—C33121.03 (18)
C3—C1—C4109.65 (15)C24—C29—C33121.11 (17)
C2—C1—C5114.29 (14)C25—C30—C31113.65 (17)
C3—C1—C5108.03 (14)C25—C30—C32110.82 (16)
C4—C1—C5109.76 (15)C31—C30—C32109.91 (17)
C1—C2—H2B109.5C25—C30—H30A107.4
C1—C2—H2C109.5C31—C30—H30A107.4
H2B—C2—H2C109.5C32—C30—H30A107.4
C1—C2—H2D109.5C30—C31—H31A109.5
H2B—C2—H2D109.5C30—C31—H31B109.5
H2C—C2—H2D109.5H31A—C31—H31B109.5
C1—C3—H3A109.5C30—C31—H31C109.5
C1—C3—H3B109.5H31A—C31—H31C109.5
H3A—C3—H3B109.5H31B—C31—H31C109.5
C1—C3—H3C109.5C30—C32—H32A109.5
H3A—C3—H3C109.5C30—C32—H32B109.5
H3B—C3—H3C109.5H32A—C32—H32B109.5
C1—C4—H4A109.5C30—C32—H32C109.5
C1—C4—H4B109.5H32A—C32—H32C109.5
H4A—C4—H4B109.5H32B—C32—H32C109.5
C1—C4—H4C109.5C29—C33—C34114.25 (17)
H4A—C4—H4C109.5C29—C33—C35110.30 (17)
H4B—C4—H4C109.5C34—C33—C35110.06 (18)
N1—C5—C6117.63 (15)C29—C33—H33A107.3
N1—C5—C1129.83 (15)C34—C33—H33A107.3
C6—C5—C1112.51 (14)C35—C33—H33A107.3
C7—C6—C5120.35 (16)C33—C34—H34A109.5
C7—C6—H6A107.2C33—C34—H34B109.5
C5—C6—H6A107.2H34A—C34—H34B109.5
C7—C6—H6B107.2C33—C34—H34C109.5
C5—C6—H6B107.2H34A—C34—H34C109.5
H6A—C6—H6B106.9H34B—C34—H34C109.5
N2—C7—C6122.46 (16)C33—C35—H35A109.5
N2—C7—C8115.91 (15)C33—C35—H35B109.5
C6—C7—C8121.23 (16)H35A—C35—H35B109.5
C10—C8—C9110.44 (15)C33—C35—H35C109.5
C10—C8—C11108.02 (16)H35A—C35—H35C109.5
C9—C8—C11108.52 (15)H35B—C35—H35C109.5
C10—C8—C7111.83 (15)C40—N3—C42126.12 (15)
C9—C8—C7109.00 (15)C39—C36—C37108.94 (17)
C11—C8—C7108.96 (14)C39—C36—C40112.04 (17)
C8—C9—H9A109.5C37—C36—C40110.84 (14)
C8—C9—H9B109.5C39—C36—C38109.8 (2)
H9A—C9—H9B109.5C37—C36—C38108.09 (18)
C8—C9—H9C109.5C40—C36—C38107.03 (16)
H9A—C9—H9C109.5C36—C37—H37A109.5
H9B—C9—H9C109.5C36—C37—H37B109.5
C8—C10—H10A109.5H37A—C37—H37B109.5
C8—C10—H10B109.5C36—C37—H37C109.5
H10A—C10—H10B109.5H37A—C37—H37C109.5
C8—C10—H10C109.5H37B—C37—H37C109.5
H10A—C10—H10C109.5C36—C38—H38A109.5
H10B—C10—H10C109.5C36—C38—H38B109.5
C8—C11—H11A109.5H38A—C38—H38B109.5
C8—C11—H11B109.5C36—C38—H38C109.5
H11A—C11—H11B109.5H38A—C38—H38C109.5
C8—C11—H11C109.5H38B—C38—H38C109.5
H11A—C11—H11C109.5C36—C39—H39A109.5
H11B—C11—H11C109.5C36—C39—H39B109.5
C17—C12—C13120.59 (16)H39A—C39—H39B109.5
C17—C12—N1119.96 (15)C36—C39—H39C109.5
C13—C12—N1118.91 (15)H39A—C39—H39C109.5
C14—C13—C12118.12 (16)H39B—C39—H39C109.5
C14—C13—C18119.94 (16)N3—C40—C41124.14 (15)
C12—C13—C18121.89 (16)N3—C40—C36115.65 (15)
C15—C14—C13122.09 (17)C41—C40—C36119.37 (13)
C15—C14—H14A119.0C40—C41—C40i126.6 (2)
C13—C14—H14A119.0C40—C41—H41A105.7
C16—C15—C14119.03 (17)C40i—C41—H41A105.7
C16—C15—H15A120.5C40—C41—H41B105.7
C14—C15—H15A120.5C40i—C41—H41B105.7
C15—C16—C17121.77 (17)H41A—C41—H41B106.1
C15—C16—H16A119.1C47—C42—C43121.32 (17)
C17—C16—H16A119.1C47—C42—N3122.39 (16)
C16—C17—C12118.31 (16)C43—C42—N3115.82 (16)
C16—C17—C21119.59 (16)C44—C43—C42118.41 (17)
C12—C17—C21122.08 (16)C44—C43—C48121.33 (17)
C13—C18—C19113.06 (15)C42—C43—C48120.08 (16)
C13—C18—C20109.72 (15)C45—C44—C43121.15 (19)
C19—C18—C20109.98 (16)C45—C44—H44A119.4
C13—C18—H18A108.0C43—C44—H44A119.4
C19—C18—H18A108.0C44—C45—C46119.97 (19)
C20—C18—H18A108.0C44—C45—H45A120.0
C18—C19—H19A109.5C46—C45—H45A120.0
C18—C19—H19B109.5C45—C46—C47121.60 (18)
H19A—C19—H19B109.5C45—C46—H46A119.2
C18—C19—H19C109.5C47—C46—H46A119.2
H19A—C19—H19C109.5C46—C47—C42117.30 (17)
H19B—C19—H19C109.5C46—C47—C51121.15 (17)
C18—C20—H20A109.5C42—C47—C51121.38 (17)
C18—C20—H20B109.5C43—C48—C49114.28 (17)
H20A—C20—H20B109.5C43—C48—C50108.98 (16)
C18—C20—H20C109.5C49—C48—C50111.21 (17)
H20A—C20—H20C109.5C43—C48—H48A107.4
H20B—C20—H20C109.5C49—C48—H48A107.4
C17—C21—C23109.73 (15)C50—C48—H48A107.4
C17—C21—C22112.30 (16)C48—C49—H49A109.5
C23—C21—C22111.16 (16)C48—C49—H49B109.5
C17—C21—H21A107.8H49A—C49—H49B109.5
C23—C21—H21A107.8C48—C49—H49C109.5
C22—C21—H21A107.8H49A—C49—H49C109.5
C21—C22—H22A109.5H49B—C49—H49C109.5
C21—C22—H22B109.5C48—C50—H50A109.5
H22A—C22—H22B109.5C48—C50—H50B109.5
C21—C22—H22C109.5H50A—C50—H50B109.5
H22A—C22—H22C109.5C48—C50—H50C109.5
H22B—C22—H22C109.5H50A—C50—H50C109.5
C21—C23—H23A109.5H50B—C50—H50C109.5
C21—C23—H23B109.5C52—C51—C53110.1 (2)
H23A—C23—H23B109.5C52—C51—C47113.73 (18)
C21—C23—H23C109.5C53—C51—C47110.67 (16)
H23A—C23—H23C109.5C52—C51—H51A107.3
H23B—C23—H23C109.5C53—C51—H51A107.3
C25—C24—C29121.44 (17)C47—C51—H51A107.3
C25—C24—N2118.97 (17)C51—C52—H52A109.5
C29—C24—N2119.33 (17)C51—C52—H52B109.5
C26—C25—C24117.80 (18)H52A—C52—H52B109.5
C26—C25—C30121.84 (18)C51—C52—H52C109.5
C24—C25—C30120.35 (17)H52A—C52—H52C109.5
C27—C26—C25121.3 (2)H52B—C52—H52C109.5
C27—C26—H26A119.3C51—C53—H53A109.5
C25—C26—H26A119.3C51—C53—H53B109.5
C26—C27—C28120.06 (19)H53A—C53—H53B109.5
C26—C27—H27A120.0C51—C53—H53C109.5
C28—C27—H27A120.0H53A—C53—H53C109.5
C27—C28—C29121.5 (2)H53B—C53—H53C109.5
C12—N1—C5—C6176.82 (16)C30—C25—C26—C27177.07 (18)
C12—N1—C5—C10.9 (3)C25—C26—C27—C280.3 (3)
C2—C1—C5—N112.3 (3)C26—C27—C28—C290.6 (3)
C3—C1—C5—N1108.6 (2)C27—C28—C29—C240.1 (3)
C4—C1—C5—N1131.85 (19)C27—C28—C29—C33177.01 (18)
C2—C1—C5—C6165.54 (16)C25—C24—C29—C281.4 (3)
C3—C1—C5—C673.54 (19)N2—C24—C29—C28175.45 (16)
C4—C1—C5—C646.0 (2)C25—C24—C29—C33175.49 (17)
N1—C5—C6—C730.8 (3)N2—C24—C29—C331.5 (3)
C1—C5—C6—C7151.06 (16)C26—C25—C30—C3120.9 (3)
C24—N2—C7—C62.3 (3)C24—C25—C30—C31160.31 (17)
C24—N2—C7—C8175.07 (16)C26—C25—C30—C32103.5 (2)
C5—C6—C7—N2111.8 (2)C24—C25—C30—C3275.3 (2)
C5—C6—C7—C875.8 (2)C28—C29—C33—C3429.1 (3)
N2—C7—C8—C10157.48 (16)C24—C29—C33—C34154.07 (18)
C6—C7—C8—C1015.4 (2)C28—C29—C33—C3595.5 (2)
N2—C7—C8—C980.13 (19)C24—C29—C33—C3581.3 (2)
C6—C7—C8—C9106.97 (19)C42—N3—C40—C419.2 (3)
N2—C7—C8—C1138.1 (2)C42—N3—C40—C36178.56 (16)
C6—C7—C8—C11134.76 (18)C39—C36—C40—N3142.66 (18)
C5—N1—C12—C1789.5 (2)C37—C36—C40—N320.7 (2)
C5—N1—C12—C1398.8 (2)C38—C36—C40—N396.9 (2)
C17—C12—C13—C143.4 (2)C39—C36—C40—C4147.4 (2)
N1—C12—C13—C14175.06 (15)C37—C36—C40—C41169.35 (16)
C17—C12—C13—C18173.90 (15)C38—C36—C40—C4173.0 (2)
N1—C12—C13—C182.3 (2)N3—C40—C41—C40i120.68 (18)
C12—C13—C14—C151.7 (3)C36—C40—C41—C40i70.32 (14)
C18—C13—C14—C15175.68 (17)C40—N3—C42—C4773.6 (2)
C13—C14—C15—C160.4 (3)C40—N3—C42—C43114.22 (19)
C14—C15—C16—C170.8 (3)C47—C42—C43—C445.7 (3)
C15—C16—C17—C120.9 (3)N3—C42—C43—C44177.99 (15)
C15—C16—C17—C21177.67 (16)C47—C42—C43—C48169.53 (16)
C13—C12—C17—C163.0 (2)N3—C42—C43—C482.7 (2)
N1—C12—C17—C16174.57 (15)C42—C43—C44—C452.3 (3)
C13—C12—C17—C21175.48 (15)C48—C43—C44—C45172.91 (17)
N1—C12—C17—C213.9 (2)C43—C44—C45—C461.3 (3)
C14—C13—C18—C1942.0 (2)C44—C45—C46—C471.6 (3)
C12—C13—C18—C19140.75 (17)C45—C46—C47—C421.7 (3)
C14—C13—C18—C2081.2 (2)C45—C46—C47—C51173.72 (17)
C12—C13—C18—C2096.1 (2)C43—C42—C47—C465.4 (2)
C16—C17—C21—C2374.5 (2)N3—C42—C47—C46177.12 (15)
C12—C17—C21—C23103.95 (19)C43—C42—C47—C51170.00 (16)
C16—C17—C21—C2249.6 (2)N3—C42—C47—C511.7 (3)
C12—C17—C21—C22131.89 (17)C44—C43—C48—C4932.5 (2)
C7—N2—C24—C25103.0 (2)C42—C43—C48—C49152.43 (17)
C7—N2—C24—C2982.8 (2)C44—C43—C48—C5092.6 (2)
C29—C24—C25—C262.3 (3)C42—C43—C48—C5082.5 (2)
N2—C24—C25—C26176.36 (16)C46—C47—C51—C5228.7 (3)
C29—C24—C25—C30176.51 (17)C42—C47—C51—C52156.1 (2)
N2—C24—C25—C302.5 (3)C46—C47—C51—C5395.9 (2)
C24—C25—C26—C271.8 (3)C42—C47—C51—C5379.3 (2)
Symmetry code: (i) x, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC35H54N2
Mr502.80
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)41.471 (4), 9.3431 (9), 24.989 (3)
β (°) 102.077 (2)
V3)9468.0 (16)
Z12
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.42 × 0.26 × 0.19
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.975, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
33069, 8317, 5827
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.124, 1.02
No. of reflections8317
No. of parameters501
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
N1—C51.270 (2)C6—C71.509 (3)
N1—C121.423 (2)N3—C401.275 (2)
N2—C71.283 (2)N3—C421.416 (2)
N2—C241.420 (2)C40—C411.527 (2)
C5—C61.530 (2)
C5—N1—C12128.60 (15)N2—C7—C8115.91 (15)
C7—N2—C24124.08 (15)C6—C7—C8121.23 (16)
N1—C5—C6117.63 (15)C40—N3—C42126.12 (15)
N1—C5—C1129.83 (15)N3—C40—C41124.14 (15)
C6—C5—C1112.51 (14)N3—C40—C36115.65 (15)
C7—C6—C5120.35 (16)C41—C40—C36119.37 (13)
N2—C7—C6122.46 (16)C40—C41—C40i126.6 (2)
Symmetry code: (i) x, y, z+1/2.
 

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