Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011783/ya6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011783/ya6044Isup2.hkl |
CCDC reference: 172214
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
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).
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.
C35H54N2 | F(000) = 3336 |
Mr = 502.80 | Dx = 1.058 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 41.471 (4) Å | Cell parameters from 7323 reflections |
b = 9.3431 (9) Å | θ = 2.2–26.3° |
c = 24.989 (3) Å | µ = 0.06 mm−1 |
β = 102.077 (2)° | T = 150 K |
V = 9468.0 (16) Å3 | Block, colourless |
Z = 12 | 0.42 × 0.26 × 0.19 mm |
Bruker SMART APEX CCD area-detector diffractometer | 8317 independent reflections |
Radiation source: fine-focus sealed tube | 5827 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −49→49 |
Tmin = 0.975, Tmax = 0.989 | k = −11→11 |
33069 measured reflections | l = −29→29 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-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 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C35H54N2 | V = 9468.0 (16) Å3 |
Mr = 502.80 | Z = 12 |
Monoclinic, C2/c | Mo Kα radiation |
a = 41.471 (4) Å | µ = 0.06 mm−1 |
b = 9.3431 (9) Å | T = 150 K |
c = 24.989 (3) Å | 0.42 × 0.26 × 0.19 mm |
β = 102.077 (2)° |
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 = 0.989 | Rint = 0.043 |
33069 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.49 e Å−3 |
8317 reflections | Δρmin = −0.25 e Å−3 |
501 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.20403 (3) | 0.83135 (15) | 0.09213 (6) | 0.0248 (3) | |
N2 | 0.12744 (4) | 0.79900 (17) | −0.03313 (6) | 0.0316 (4) | |
C1 | 0.16297 (4) | 0.87388 (19) | 0.15363 (7) | 0.0263 (4) | |
C2 | 0.18945 (5) | 0.8527 (2) | 0.20558 (7) | 0.0383 (5) | |
H2B | 0.1793 | 0.8559 | 0.2376 | 0.057* | |
H2C | 0.2059 | 0.9290 | 0.2084 | 0.057* | |
H2D | 0.2002 | 0.7597 | 0.2041 | 0.057* | |
C3 | 0.13716 (5) | 0.7545 (2) | 0.15055 (8) | 0.0374 (5) | |
H3A | 0.1285 | 0.7546 | 0.1841 | 0.056* | |
H3B | 0.1475 | 0.6617 | 0.1466 | 0.056* | |
H3C | 0.1191 | 0.7709 | 0.1189 | 0.056* | |
C4 | 0.14686 (5) | 1.0197 (2) | 0.15943 (8) | 0.0364 (5) | |
H4A | 0.1385 | 1.0213 | 0.1933 | 0.055* | |
H4B | 0.1286 | 1.0351 | 0.1281 | 0.055* | |
H4C | 0.1632 | 1.0959 | 0.1605 | 0.055* | |
C5 | 0.17610 (4) | 0.87051 (18) | 0.10016 (7) | 0.0240 (4) | |
C6 | 0.15109 (4) | 0.9287 (2) | 0.05112 (7) | 0.0359 (5) | |
H6A | 0.1288 | 0.9109 | 0.0583 | 0.043* | |
H6B | 0.1540 | 1.0339 | 0.0507 | 0.043* | |
C7 | 0.15099 (4) | 0.87509 (19) | −0.00586 (7) | 0.0248 (4) | |
C8 | 0.17728 (4) | 0.9244 (2) | −0.03722 (7) | 0.0286 (4) | |
C9 | 0.20138 (5) | 0.8010 (2) | −0.03904 (8) | 0.0363 (5) | |
H9A | 0.1892 | 0.7171 | −0.0560 | 0.055* | |
H9B | 0.2129 | 0.7772 | −0.0017 | 0.055* | |
H9C | 0.2175 | 0.8299 | −0.0606 | 0.055* | |
C10 | 0.19574 (5) | 1.0566 (2) | −0.01127 (8) | 0.0396 (5) | |
H10A | 0.1800 | 1.1345 | −0.0105 | 0.059* | |
H10B | 0.2118 | 1.0862 | −0.0328 | 0.059* | |
H10C | 0.2073 | 1.0341 | 0.0262 | 0.059* | |
C11 | 0.16028 (5) | 0.9624 (2) | −0.09604 (8) | 0.0437 (5) | |
H11A | 0.1482 | 0.8789 | −0.1135 | 0.066* | |
H11B | 0.1769 | 0.9908 | −0.1166 | 0.066* | |
H11C | 0.1449 | 1.0418 | −0.0956 | 0.066* | |
C12 | 0.23179 (4) | 0.78032 (18) | 0.13089 (7) | 0.0241 (4) | |
C13 | 0.25773 (4) | 0.87647 (19) | 0.15185 (7) | 0.0257 (4) | |
C14 | 0.28565 (4) | 0.8226 (2) | 0.18620 (7) | 0.0316 (4) | |
H14A | 0.3030 | 0.8864 | 0.2013 | 0.038* | |
C15 | 0.28911 (5) | 0.6788 (2) | 0.19919 (8) | 0.0335 (5) | |
H15A | 0.3085 | 0.6445 | 0.2231 | 0.040* | |
C16 | 0.26406 (4) | 0.5859 (2) | 0.17699 (7) | 0.0319 (4) | |
H16A | 0.2665 | 0.4868 | 0.1855 | 0.038* | |
C17 | 0.23520 (4) | 0.63329 (19) | 0.14240 (7) | 0.0263 (4) | |
C18 | 0.25620 (4) | 1.03292 (19) | 0.13577 (7) | 0.0293 (4) | |
H18A | 0.2325 | 1.0589 | 0.1221 | 0.035* | |
C19 | 0.27030 (5) | 1.1322 (2) | 0.18343 (9) | 0.0441 (5) | |
H19A | 0.2585 | 1.1173 | 0.2131 | 0.066* | |
H19B | 0.2677 | 1.2319 | 0.1711 | 0.066* | |
H19C | 0.2938 | 1.1111 | 0.1967 | 0.066* | |
C20 | 0.27432 (5) | 1.0558 (2) | 0.08906 (9) | 0.0431 (5) | |
H20A | 0.2651 | 0.9919 | 0.0586 | 0.065* | |
H20B | 0.2978 | 1.0347 | 0.1020 | 0.065* | |
H20C | 0.2717 | 1.1554 | 0.0767 | 0.065* | |
C21 | 0.20890 (4) | 0.52544 (19) | 0.11730 (7) | 0.0299 (4) | |
H21A | 0.1885 | 0.5798 | 0.1006 | 0.036* | |
C22 | 0.20019 (5) | 0.4229 (2) | 0.16012 (8) | 0.0395 (5) | |
H22A | 0.1928 | 0.4782 | 0.1887 | 0.059* | |
H22B | 0.2197 | 0.3666 | 0.1765 | 0.059* | |
H22C | 0.1825 | 0.3585 | 0.1425 | 0.059* | |
C23 | 0.22010 (5) | 0.4433 (2) | 0.07154 (9) | 0.0427 (5) | |
H23A | 0.2253 | 0.5111 | 0.0446 | 0.064* | |
H23B | 0.2024 | 0.3790 | 0.0537 | 0.064* | |
H23C | 0.2398 | 0.3870 | 0.0870 | 0.064* | |
C24 | 0.09973 (5) | 0.7528 (2) | −0.01259 (7) | 0.0322 (4) | |
C25 | 0.09847 (5) | 0.6100 (2) | 0.00478 (7) | 0.0329 (4) | |
C26 | 0.07011 (5) | 0.5651 (2) | 0.02182 (8) | 0.0380 (5) | |
H26A | 0.0689 | 0.4700 | 0.0347 | 0.046* | |
C27 | 0.04381 (5) | 0.6559 (2) | 0.02033 (8) | 0.0424 (5) | |
H27A | 0.0247 | 0.6231 | 0.0319 | 0.051* | |
C28 | 0.04516 (5) | 0.7945 (2) | 0.00200 (8) | 0.0407 (5) | |
H28A | 0.0267 | 0.8558 | 0.0008 | 0.049* | |
C29 | 0.07286 (5) | 0.8467 (2) | −0.01480 (8) | 0.0346 (5) | |
C30 | 0.12693 (5) | 0.5091 (2) | 0.00371 (8) | 0.0359 (5) | |
H30A | 0.1478 | 0.5636 | 0.0172 | 0.043* | |
C31 | 0.12755 (5) | 0.3789 (2) | 0.04053 (9) | 0.0489 (6) | |
H31A | 0.1279 | 0.4104 | 0.0780 | 0.073* | |
H31B | 0.1473 | 0.3219 | 0.0400 | 0.073* | |
H31C | 0.1079 | 0.3205 | 0.0273 | 0.073* | |
C32 | 0.12696 (6) | 0.4610 (2) | −0.05500 (9) | 0.0487 (6) | |
H32A | 0.1270 | 0.5453 | −0.0783 | 0.073* | |
H32B | 0.1072 | 0.4035 | −0.0690 | 0.073* | |
H32C | 0.1467 | 0.4034 | −0.0552 | 0.073* | |
C33 | 0.07342 (5) | 0.9974 (2) | −0.03751 (8) | 0.0381 (5) | |
H33A | 0.0966 | 1.0329 | −0.0269 | 0.046* | |
C34 | 0.05168 (6) | 1.1039 (3) | −0.01514 (10) | 0.0554 (6) | |
H34A | 0.0577 | 1.1042 | 0.0249 | 0.083* | |
H34B | 0.0285 | 1.0760 | −0.0270 | 0.083* | |
H34C | 0.0549 | 1.1998 | −0.0290 | 0.083* | |
C35 | 0.06415 (6) | 0.9949 (3) | −0.10001 (9) | 0.0546 (6) | |
H35A | 0.0784 | 0.9268 | −0.1140 | 0.082* | |
H35B | 0.0671 | 1.0907 | −0.1143 | 0.082* | |
H35C | 0.0411 | 0.9656 | −0.1118 | 0.082* | |
N3 | 0.04350 (3) | 0.56371 (15) | 0.19867 (6) | 0.0265 (3) | |
C36 | −0.00924 (4) | 0.4675 (2) | 0.15912 (8) | 0.0327 (4) | |
C37 | 0.01013 (5) | 0.3793 (2) | 0.12533 (8) | 0.0393 (5) | |
H37A | 0.0226 | 0.3049 | 0.1484 | 0.059* | |
H37B | 0.0254 | 0.4418 | 0.1111 | 0.059* | |
H37C | −0.0052 | 0.3345 | 0.0947 | 0.059* | |
C38 | −0.02884 (6) | 0.5824 (3) | 0.12150 (11) | 0.0678 (8) | |
H38A | −0.0415 | 0.6406 | 0.1425 | 0.102* | |
H38B | −0.0440 | 0.5357 | 0.0911 | 0.102* | |
H38C | −0.0135 | 0.6438 | 0.1070 | 0.102* | |
C39 | −0.03273 (6) | 0.3701 (3) | 0.18060 (11) | 0.0650 (8) | |
H39A | −0.0201 | 0.2975 | 0.2046 | 0.097* | |
H39B | −0.0474 | 0.3229 | 0.1498 | 0.097* | |
H39C | −0.0459 | 0.4266 | 0.2013 | 0.097* | |
C40 | 0.01407 (4) | 0.54663 (18) | 0.20530 (7) | 0.0248 (4) | |
C41 | 0.0000 | 0.6200 (3) | 0.2500 | 0.0314 (6) | |
H41A | −0.0177 | 0.6837 | 0.2306 | 0.038* | 0.50 |
H41B | 0.0177 | 0.6837 | 0.2694 | 0.038* | 0.50 |
C42 | 0.06920 (4) | 0.63572 (19) | 0.23488 (7) | 0.0261 (4) | |
C43 | 0.09599 (4) | 0.5499 (2) | 0.26040 (7) | 0.0285 (4) | |
C44 | 0.12235 (5) | 0.6153 (2) | 0.29493 (8) | 0.0347 (5) | |
H44A | 0.1402 | 0.5584 | 0.3135 | 0.042* | |
C45 | 0.12310 (5) | 0.7610 (2) | 0.30284 (8) | 0.0404 (5) | |
H45A | 0.1412 | 0.8038 | 0.3273 | 0.048* | |
C46 | 0.09755 (5) | 0.8452 (2) | 0.27521 (8) | 0.0373 (5) | |
H46A | 0.0986 | 0.9460 | 0.2803 | 0.045* | |
C47 | 0.07020 (4) | 0.7857 (2) | 0.24004 (7) | 0.0297 (4) | |
C48 | 0.09675 (4) | 0.3918 (2) | 0.24642 (8) | 0.0329 (4) | |
H48A | 0.0735 | 0.3567 | 0.2386 | 0.040* | |
C49 | 0.11621 (5) | 0.2993 (2) | 0.29231 (10) | 0.0505 (6) | |
H49A | 0.1073 | 0.3119 | 0.3254 | 0.076* | |
H49B | 0.1394 | 0.3280 | 0.2998 | 0.076* | |
H49C | 0.1143 | 0.1985 | 0.2812 | 0.076* | |
C50 | 0.10978 (6) | 0.3750 (2) | 0.19376 (10) | 0.0526 (6) | |
H50A | 0.0969 | 0.4354 | 0.1650 | 0.079* | |
H50B | 0.1078 | 0.2747 | 0.1820 | 0.079* | |
H50C | 0.1330 | 0.4041 | 0.2005 | 0.079* | |
C51 | 0.04393 (5) | 0.8799 (2) | 0.20547 (8) | 0.0353 (5) | |
H51A | 0.0224 | 0.8290 | 0.2017 | 0.042* | |
C52 | 0.04028 (8) | 1.0244 (3) | 0.23072 (12) | 0.0858 (10) | |
H52A | 0.0359 | 1.0112 | 0.2675 | 0.129* | |
H52B | 0.0219 | 1.0763 | 0.2079 | 0.129* | |
H52C | 0.0607 | 1.0793 | 0.2332 | 0.129* | |
C53 | 0.05044 (6) | 0.8985 (3) | 0.14854 (10) | 0.0715 (8) | |
H53A | 0.0332 | 0.9590 | 0.1269 | 0.107* | |
H53B | 0.0503 | 0.8046 | 0.1310 | 0.107* | |
H53C | 0.0720 | 0.9438 | 0.1509 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0264 (8) | 0.0244 (8) | 0.0237 (8) | −0.0015 (6) | 0.0054 (6) | 0.0006 (6) |
N2 | 0.0335 (9) | 0.0338 (9) | 0.0293 (9) | −0.0027 (7) | 0.0109 (7) | −0.0030 (7) |
C1 | 0.0282 (9) | 0.0281 (10) | 0.0233 (10) | 0.0020 (8) | 0.0071 (7) | −0.0016 (8) |
C2 | 0.0397 (11) | 0.0553 (14) | 0.0216 (10) | 0.0108 (10) | 0.0105 (8) | −0.0009 (9) |
C3 | 0.0436 (12) | 0.0366 (11) | 0.0385 (12) | −0.0034 (9) | 0.0233 (10) | −0.0030 (9) |
C4 | 0.0387 (11) | 0.0339 (11) | 0.0383 (12) | 0.0050 (9) | 0.0122 (9) | −0.0011 (9) |
C5 | 0.0248 (9) | 0.0222 (9) | 0.0247 (10) | −0.0040 (7) | 0.0043 (7) | 0.0003 (7) |
C6 | 0.0252 (10) | 0.0547 (13) | 0.0287 (10) | 0.0006 (9) | 0.0075 (8) | 0.0030 (9) |
C7 | 0.0255 (9) | 0.0243 (9) | 0.0244 (10) | 0.0081 (8) | 0.0048 (7) | 0.0033 (7) |
C8 | 0.0287 (10) | 0.0316 (10) | 0.0264 (10) | 0.0028 (8) | 0.0081 (8) | 0.0037 (8) |
C9 | 0.0362 (11) | 0.0405 (12) | 0.0368 (11) | 0.0047 (9) | 0.0178 (9) | 0.0011 (9) |
C10 | 0.0398 (11) | 0.0377 (12) | 0.0446 (12) | −0.0035 (9) | 0.0164 (10) | 0.0013 (9) |
C11 | 0.0427 (12) | 0.0589 (14) | 0.0326 (11) | 0.0032 (11) | 0.0146 (9) | 0.0140 (10) |
C12 | 0.0263 (9) | 0.0294 (10) | 0.0183 (9) | 0.0035 (8) | 0.0087 (7) | −0.0002 (7) |
C13 | 0.0273 (9) | 0.0280 (10) | 0.0234 (9) | 0.0026 (8) | 0.0090 (7) | −0.0022 (8) |
C14 | 0.0278 (10) | 0.0360 (11) | 0.0300 (11) | −0.0012 (8) | 0.0038 (8) | −0.0043 (8) |
C15 | 0.0294 (10) | 0.0361 (11) | 0.0330 (11) | 0.0068 (9) | 0.0021 (8) | 0.0050 (9) |
C16 | 0.0355 (11) | 0.0274 (10) | 0.0339 (11) | 0.0054 (9) | 0.0099 (9) | 0.0047 (8) |
C17 | 0.0282 (10) | 0.0278 (10) | 0.0249 (10) | 0.0017 (8) | 0.0102 (8) | 0.0012 (8) |
C18 | 0.0274 (10) | 0.0270 (10) | 0.0331 (11) | 0.0008 (8) | 0.0052 (8) | −0.0021 (8) |
C19 | 0.0465 (12) | 0.0320 (12) | 0.0497 (13) | 0.0030 (10) | 0.0008 (10) | −0.0085 (10) |
C20 | 0.0494 (13) | 0.0318 (12) | 0.0530 (14) | 0.0055 (10) | 0.0217 (11) | 0.0075 (10) |
C21 | 0.0313 (10) | 0.0273 (10) | 0.0323 (11) | 0.0027 (8) | 0.0095 (8) | 0.0030 (8) |
C22 | 0.0373 (11) | 0.0363 (12) | 0.0466 (13) | −0.0014 (9) | 0.0122 (9) | 0.0074 (9) |
C23 | 0.0464 (12) | 0.0378 (12) | 0.0474 (13) | −0.0058 (10) | 0.0174 (10) | −0.0104 (10) |
C24 | 0.0341 (11) | 0.0396 (12) | 0.0242 (10) | −0.0046 (9) | 0.0091 (8) | −0.0068 (8) |
C25 | 0.0340 (11) | 0.0404 (12) | 0.0235 (10) | −0.0055 (9) | 0.0044 (8) | −0.0038 (8) |
C26 | 0.0410 (12) | 0.0437 (12) | 0.0295 (11) | −0.0087 (10) | 0.0079 (9) | −0.0011 (9) |
C27 | 0.0380 (12) | 0.0561 (15) | 0.0364 (12) | −0.0091 (10) | 0.0151 (9) | −0.0032 (10) |
C28 | 0.0355 (11) | 0.0511 (14) | 0.0372 (12) | 0.0023 (10) | 0.0111 (9) | −0.0063 (10) |
C29 | 0.0351 (11) | 0.0413 (12) | 0.0278 (11) | −0.0031 (9) | 0.0075 (8) | −0.0050 (9) |
C30 | 0.0349 (11) | 0.0359 (11) | 0.0355 (11) | −0.0044 (9) | 0.0039 (9) | −0.0014 (9) |
C31 | 0.0457 (13) | 0.0458 (13) | 0.0532 (14) | −0.0012 (11) | 0.0057 (11) | 0.0060 (11) |
C32 | 0.0531 (14) | 0.0512 (14) | 0.0426 (13) | 0.0105 (11) | 0.0116 (11) | −0.0052 (10) |
C33 | 0.0357 (11) | 0.0406 (12) | 0.0371 (12) | 0.0021 (9) | 0.0060 (9) | −0.0025 (9) |
C34 | 0.0532 (14) | 0.0480 (14) | 0.0665 (16) | 0.0054 (11) | 0.0161 (12) | −0.0054 (12) |
C35 | 0.0687 (16) | 0.0503 (14) | 0.0425 (14) | 0.0000 (12) | 0.0061 (12) | 0.0023 (11) |
N3 | 0.0267 (8) | 0.0247 (8) | 0.0293 (8) | −0.0005 (6) | 0.0088 (7) | −0.0011 (6) |
C36 | 0.0265 (10) | 0.0311 (11) | 0.0397 (11) | −0.0005 (8) | 0.0050 (8) | −0.0036 (9) |
C37 | 0.0393 (11) | 0.0452 (13) | 0.0323 (11) | −0.0050 (10) | 0.0052 (9) | −0.0099 (9) |
C38 | 0.0625 (16) | 0.0556 (16) | 0.0671 (17) | 0.0167 (13) | −0.0278 (13) | −0.0115 (13) |
C39 | 0.0613 (15) | 0.0655 (17) | 0.0790 (18) | −0.0355 (13) | 0.0396 (14) | −0.0366 (14) |
C40 | 0.0275 (10) | 0.0200 (9) | 0.0287 (10) | 0.0040 (7) | 0.0097 (8) | 0.0053 (7) |
C41 | 0.0321 (14) | 0.0248 (14) | 0.0403 (16) | 0.000 | 0.0147 (12) | 0.000 |
C42 | 0.0271 (9) | 0.0283 (10) | 0.0262 (10) | −0.0027 (8) | 0.0129 (8) | −0.0053 (8) |
C43 | 0.0260 (9) | 0.0308 (10) | 0.0320 (10) | −0.0028 (8) | 0.0133 (8) | −0.0018 (8) |
C44 | 0.0295 (10) | 0.0415 (12) | 0.0338 (11) | −0.0009 (9) | 0.0081 (8) | −0.0021 (9) |
C45 | 0.0381 (12) | 0.0481 (13) | 0.0347 (12) | −0.0105 (10) | 0.0071 (9) | −0.0129 (10) |
C46 | 0.0475 (12) | 0.0272 (11) | 0.0419 (12) | −0.0099 (9) | 0.0204 (10) | −0.0117 (9) |
C47 | 0.0340 (10) | 0.0285 (10) | 0.0310 (10) | −0.0021 (8) | 0.0171 (8) | −0.0032 (8) |
C48 | 0.0242 (10) | 0.0290 (11) | 0.0475 (12) | 0.0009 (8) | 0.0118 (9) | 0.0003 (9) |
C49 | 0.0361 (12) | 0.0381 (13) | 0.0748 (16) | 0.0017 (10) | 0.0058 (11) | 0.0065 (11) |
C50 | 0.0609 (15) | 0.0349 (12) | 0.0726 (17) | 0.0046 (11) | 0.0384 (13) | −0.0097 (11) |
C51 | 0.0381 (11) | 0.0263 (10) | 0.0454 (12) | 0.0002 (9) | 0.0176 (9) | 0.0016 (9) |
C52 | 0.120 (3) | 0.0432 (16) | 0.082 (2) | 0.0374 (16) | −0.0071 (18) | −0.0103 (14) |
C53 | 0.0538 (15) | 0.115 (2) | 0.0479 (15) | 0.0253 (16) | 0.0152 (12) | 0.0267 (15) |
N1—C5 | 1.270 (2) | C27—H27A | 0.9500 |
N1—C12 | 1.423 (2) | C28—C29 | 1.391 (3) |
N2—C7 | 1.283 (2) | C28—H28A | 0.9500 |
N2—C24 | 1.420 (2) | C29—C33 | 1.521 (3) |
C1—C2 | 1.528 (2) | C30—C31 | 1.522 (3) |
C1—C3 | 1.537 (3) | C30—C32 | 1.535 (3) |
C1—C4 | 1.538 (2) | C30—H30A | 1.0000 |
C1—C5 | 1.545 (2) | C31—H31A | 0.9800 |
C2—H2B | 0.9800 | C31—H31B | 0.9800 |
C2—H2C | 0.9800 | C31—H31C | 0.9800 |
C2—H2D | 0.9800 | C32—H32A | 0.9800 |
C3—H3A | 0.9800 | C32—H32B | 0.9800 |
C3—H3B | 0.9800 | C32—H32C | 0.9800 |
C3—H3C | 0.9800 | C33—C34 | 1.525 (3) |
C4—H4A | 0.9800 | C33—C35 | 1.528 (3) |
C4—H4B | 0.9800 | C33—H33A | 1.0000 |
C4—H4C | 0.9800 | C34—H34A | 0.9800 |
C5—C6 | 1.530 (2) | C34—H34B | 0.9800 |
C6—C7 | 1.509 (3) | C34—H34C | 0.9800 |
C6—H6A | 0.9900 | C35—H35A | 0.9800 |
C6—H6B | 0.9900 | C35—H35B | 0.9800 |
C7—C8 | 1.540 (2) | C35—H35C | 0.9800 |
C8—C10 | 1.525 (3) | N3—C40 | 1.275 (2) |
C8—C9 | 1.533 (3) | N3—C42 | 1.416 (2) |
C8—C11 | 1.533 (3) | C36—C39 | 1.512 (3) |
C9—H9A | 0.9800 | C36—C37 | 1.524 (3) |
C9—H9B | 0.9800 | C36—C40 | 1.531 (3) |
C9—H9C | 0.9800 | C36—C38 | 1.541 (3) |
C10—H10A | 0.9800 | C37—H37A | 0.9800 |
C10—H10B | 0.9800 | C37—H37B | 0.9800 |
C10—H10C | 0.9800 | C37—H37C | 0.9800 |
C11—H11A | 0.9800 | C38—H38A | 0.9800 |
C11—H11B | 0.9800 | C38—H38B | 0.9800 |
C11—H11C | 0.9800 | C38—H38C | 0.9800 |
C12—C17 | 1.405 (2) | C39—H39A | 0.9800 |
C12—C13 | 1.415 (2) | C39—H39B | 0.9800 |
C13—C14 | 1.384 (2) | C39—H39C | 0.9800 |
C13—C18 | 1.514 (2) | C40—C41 | 1.527 (2) |
C14—C15 | 1.383 (3) | C41—C40i | 1.527 (2) |
C14—H14A | 0.9500 | C41—H41A | 0.9900 |
C15—C16 | 1.378 (3) | C41—H41B | 0.9900 |
C15—H15A | 0.9500 | C42—C47 | 1.407 (3) |
C16—C17 | 1.394 (2) | C42—C43 | 1.410 (3) |
C16—H16A | 0.9500 | C43—C44 | 1.385 (3) |
C17—C21 | 1.520 (2) | C43—C48 | 1.520 (3) |
C18—C19 | 1.526 (3) | C44—C45 | 1.375 (3) |
C18—C20 | 1.529 (3) | C44—H44A | 0.9500 |
C18—H18A | 1.0000 | C45—C46 | 1.383 (3) |
C19—H19A | 0.9800 | C45—H45A | 0.9500 |
C19—H19B | 0.9800 | C46—C47 | 1.397 (3) |
C19—H19C | 0.9800 | C46—H46A | 0.9500 |
C20—H20A | 0.9800 | C47—C51 | 1.522 (3) |
C20—H20B | 0.9800 | C48—C49 | 1.525 (3) |
C20—H20C | 0.9800 | C48—C50 | 1.532 (3) |
C21—C23 | 1.528 (3) | C48—H48A | 1.0000 |
C21—C22 | 1.534 (3) | C49—H49A | 0.9800 |
C21—H21A | 1.0000 | C49—H49B | 0.9800 |
C22—H22A | 0.9800 | C49—H49C | 0.9800 |
C22—H22B | 0.9800 | C50—H50A | 0.9800 |
C22—H22C | 0.9800 | C50—H50B | 0.9800 |
C23—H23A | 0.9800 | C50—H50C | 0.9800 |
C23—H23B | 0.9800 | C51—C52 | 1.510 (3) |
C23—H23C | 0.9800 | C51—C53 | 1.512 (3) |
C24—C25 | 1.408 (3) | C51—H51A | 1.0000 |
C24—C29 | 1.410 (3) | C52—H52A | 0.9800 |
C25—C26 | 1.396 (3) | C52—H52B | 0.9800 |
C25—C30 | 1.515 (3) | C52—H52C | 0.9800 |
C26—C27 | 1.376 (3) | C53—H53A | 0.9800 |
C26—H26A | 0.9500 | C53—H53B | 0.9800 |
C27—C28 | 1.378 (3) | C53—H53C | 0.9800 |
C5—N1—C12 | 128.60 (15) | C27—C28—H28A | 119.2 |
C7—N2—C24 | 124.08 (15) | C29—C28—H28A | 119.2 |
C2—C1—C3 | 108.55 (16) | C28—C29—C24 | 117.78 (19) |
C2—C1—C4 | 106.49 (15) | C28—C29—C33 | 121.03 (18) |
C3—C1—C4 | 109.65 (15) | C24—C29—C33 | 121.11 (17) |
C2—C1—C5 | 114.29 (14) | C25—C30—C31 | 113.65 (17) |
C3—C1—C5 | 108.03 (14) | C25—C30—C32 | 110.82 (16) |
C4—C1—C5 | 109.76 (15) | C31—C30—C32 | 109.91 (17) |
C1—C2—H2B | 109.5 | C25—C30—H30A | 107.4 |
C1—C2—H2C | 109.5 | C31—C30—H30A | 107.4 |
H2B—C2—H2C | 109.5 | C32—C30—H30A | 107.4 |
C1—C2—H2D | 109.5 | C30—C31—H31A | 109.5 |
H2B—C2—H2D | 109.5 | C30—C31—H31B | 109.5 |
H2C—C2—H2D | 109.5 | H31A—C31—H31B | 109.5 |
C1—C3—H3A | 109.5 | C30—C31—H31C | 109.5 |
C1—C3—H3B | 109.5 | H31A—C31—H31C | 109.5 |
H3A—C3—H3B | 109.5 | H31B—C31—H31C | 109.5 |
C1—C3—H3C | 109.5 | C30—C32—H32A | 109.5 |
H3A—C3—H3C | 109.5 | C30—C32—H32B | 109.5 |
H3B—C3—H3C | 109.5 | H32A—C32—H32B | 109.5 |
C1—C4—H4A | 109.5 | C30—C32—H32C | 109.5 |
C1—C4—H4B | 109.5 | H32A—C32—H32C | 109.5 |
H4A—C4—H4B | 109.5 | H32B—C32—H32C | 109.5 |
C1—C4—H4C | 109.5 | C29—C33—C34 | 114.25 (17) |
H4A—C4—H4C | 109.5 | C29—C33—C35 | 110.30 (17) |
H4B—C4—H4C | 109.5 | C34—C33—C35 | 110.06 (18) |
N1—C5—C6 | 117.63 (15) | C29—C33—H33A | 107.3 |
N1—C5—C1 | 129.83 (15) | C34—C33—H33A | 107.3 |
C6—C5—C1 | 112.51 (14) | C35—C33—H33A | 107.3 |
C7—C6—C5 | 120.35 (16) | C33—C34—H34A | 109.5 |
C7—C6—H6A | 107.2 | C33—C34—H34B | 109.5 |
C5—C6—H6A | 107.2 | H34A—C34—H34B | 109.5 |
C7—C6—H6B | 107.2 | C33—C34—H34C | 109.5 |
C5—C6—H6B | 107.2 | H34A—C34—H34C | 109.5 |
H6A—C6—H6B | 106.9 | H34B—C34—H34C | 109.5 |
N2—C7—C6 | 122.46 (16) | C33—C35—H35A | 109.5 |
N2—C7—C8 | 115.91 (15) | C33—C35—H35B | 109.5 |
C6—C7—C8 | 121.23 (16) | H35A—C35—H35B | 109.5 |
C10—C8—C9 | 110.44 (15) | C33—C35—H35C | 109.5 |
C10—C8—C11 | 108.02 (16) | H35A—C35—H35C | 109.5 |
C9—C8—C11 | 108.52 (15) | H35B—C35—H35C | 109.5 |
C10—C8—C7 | 111.83 (15) | C40—N3—C42 | 126.12 (15) |
C9—C8—C7 | 109.00 (15) | C39—C36—C37 | 108.94 (17) |
C11—C8—C7 | 108.96 (14) | C39—C36—C40 | 112.04 (17) |
C8—C9—H9A | 109.5 | C37—C36—C40 | 110.84 (14) |
C8—C9—H9B | 109.5 | C39—C36—C38 | 109.8 (2) |
H9A—C9—H9B | 109.5 | C37—C36—C38 | 108.09 (18) |
C8—C9—H9C | 109.5 | C40—C36—C38 | 107.03 (16) |
H9A—C9—H9C | 109.5 | C36—C37—H37A | 109.5 |
H9B—C9—H9C | 109.5 | C36—C37—H37B | 109.5 |
C8—C10—H10A | 109.5 | H37A—C37—H37B | 109.5 |
C8—C10—H10B | 109.5 | C36—C37—H37C | 109.5 |
H10A—C10—H10B | 109.5 | H37A—C37—H37C | 109.5 |
C8—C10—H10C | 109.5 | H37B—C37—H37C | 109.5 |
H10A—C10—H10C | 109.5 | C36—C38—H38A | 109.5 |
H10B—C10—H10C | 109.5 | C36—C38—H38B | 109.5 |
C8—C11—H11A | 109.5 | H38A—C38—H38B | 109.5 |
C8—C11—H11B | 109.5 | C36—C38—H38C | 109.5 |
H11A—C11—H11B | 109.5 | H38A—C38—H38C | 109.5 |
C8—C11—H11C | 109.5 | H38B—C38—H38C | 109.5 |
H11A—C11—H11C | 109.5 | C36—C39—H39A | 109.5 |
H11B—C11—H11C | 109.5 | C36—C39—H39B | 109.5 |
C17—C12—C13 | 120.59 (16) | H39A—C39—H39B | 109.5 |
C17—C12—N1 | 119.96 (15) | C36—C39—H39C | 109.5 |
C13—C12—N1 | 118.91 (15) | H39A—C39—H39C | 109.5 |
C14—C13—C12 | 118.12 (16) | H39B—C39—H39C | 109.5 |
C14—C13—C18 | 119.94 (16) | N3—C40—C41 | 124.14 (15) |
C12—C13—C18 | 121.89 (16) | N3—C40—C36 | 115.65 (15) |
C15—C14—C13 | 122.09 (17) | C41—C40—C36 | 119.37 (13) |
C15—C14—H14A | 119.0 | C40—C41—C40i | 126.6 (2) |
C13—C14—H14A | 119.0 | C40—C41—H41A | 105.7 |
C16—C15—C14 | 119.03 (17) | C40i—C41—H41A | 105.7 |
C16—C15—H15A | 120.5 | C40—C41—H41B | 105.7 |
C14—C15—H15A | 120.5 | C40i—C41—H41B | 105.7 |
C15—C16—C17 | 121.77 (17) | H41A—C41—H41B | 106.1 |
C15—C16—H16A | 119.1 | C47—C42—C43 | 121.32 (17) |
C17—C16—H16A | 119.1 | C47—C42—N3 | 122.39 (16) |
C16—C17—C12 | 118.31 (16) | C43—C42—N3 | 115.82 (16) |
C16—C17—C21 | 119.59 (16) | C44—C43—C42 | 118.41 (17) |
C12—C17—C21 | 122.08 (16) | C44—C43—C48 | 121.33 (17) |
C13—C18—C19 | 113.06 (15) | C42—C43—C48 | 120.08 (16) |
C13—C18—C20 | 109.72 (15) | C45—C44—C43 | 121.15 (19) |
C19—C18—C20 | 109.98 (16) | C45—C44—H44A | 119.4 |
C13—C18—H18A | 108.0 | C43—C44—H44A | 119.4 |
C19—C18—H18A | 108.0 | C44—C45—C46 | 119.97 (19) |
C20—C18—H18A | 108.0 | C44—C45—H45A | 120.0 |
C18—C19—H19A | 109.5 | C46—C45—H45A | 120.0 |
C18—C19—H19B | 109.5 | C45—C46—C47 | 121.60 (18) |
H19A—C19—H19B | 109.5 | C45—C46—H46A | 119.2 |
C18—C19—H19C | 109.5 | C47—C46—H46A | 119.2 |
H19A—C19—H19C | 109.5 | C46—C47—C42 | 117.30 (17) |
H19B—C19—H19C | 109.5 | C46—C47—C51 | 121.15 (17) |
C18—C20—H20A | 109.5 | C42—C47—C51 | 121.38 (17) |
C18—C20—H20B | 109.5 | C43—C48—C49 | 114.28 (17) |
H20A—C20—H20B | 109.5 | C43—C48—C50 | 108.98 (16) |
C18—C20—H20C | 109.5 | C49—C48—C50 | 111.21 (17) |
H20A—C20—H20C | 109.5 | C43—C48—H48A | 107.4 |
H20B—C20—H20C | 109.5 | C49—C48—H48A | 107.4 |
C17—C21—C23 | 109.73 (15) | C50—C48—H48A | 107.4 |
C17—C21—C22 | 112.30 (16) | C48—C49—H49A | 109.5 |
C23—C21—C22 | 111.16 (16) | C48—C49—H49B | 109.5 |
C17—C21—H21A | 107.8 | H49A—C49—H49B | 109.5 |
C23—C21—H21A | 107.8 | C48—C49—H49C | 109.5 |
C22—C21—H21A | 107.8 | H49A—C49—H49C | 109.5 |
C21—C22—H22A | 109.5 | H49B—C49—H49C | 109.5 |
C21—C22—H22B | 109.5 | C48—C50—H50A | 109.5 |
H22A—C22—H22B | 109.5 | C48—C50—H50B | 109.5 |
C21—C22—H22C | 109.5 | H50A—C50—H50B | 109.5 |
H22A—C22—H22C | 109.5 | C48—C50—H50C | 109.5 |
H22B—C22—H22C | 109.5 | H50A—C50—H50C | 109.5 |
C21—C23—H23A | 109.5 | H50B—C50—H50C | 109.5 |
C21—C23—H23B | 109.5 | C52—C51—C53 | 110.1 (2) |
H23A—C23—H23B | 109.5 | C52—C51—C47 | 113.73 (18) |
C21—C23—H23C | 109.5 | C53—C51—C47 | 110.67 (16) |
H23A—C23—H23C | 109.5 | C52—C51—H51A | 107.3 |
H23B—C23—H23C | 109.5 | C53—C51—H51A | 107.3 |
C25—C24—C29 | 121.44 (17) | C47—C51—H51A | 107.3 |
C25—C24—N2 | 118.97 (17) | C51—C52—H52A | 109.5 |
C29—C24—N2 | 119.33 (17) | C51—C52—H52B | 109.5 |
C26—C25—C24 | 117.80 (18) | H52A—C52—H52B | 109.5 |
C26—C25—C30 | 121.84 (18) | C51—C52—H52C | 109.5 |
C24—C25—C30 | 120.35 (17) | H52A—C52—H52C | 109.5 |
C27—C26—C25 | 121.3 (2) | H52B—C52—H52C | 109.5 |
C27—C26—H26A | 119.3 | C51—C53—H53A | 109.5 |
C25—C26—H26A | 119.3 | C51—C53—H53B | 109.5 |
C26—C27—C28 | 120.06 (19) | H53A—C53—H53B | 109.5 |
C26—C27—H27A | 120.0 | C51—C53—H53C | 109.5 |
C28—C27—H27A | 120.0 | H53A—C53—H53C | 109.5 |
C27—C28—C29 | 121.5 (2) | H53B—C53—H53C | 109.5 |
C12—N1—C5—C6 | 176.82 (16) | C30—C25—C26—C27 | −177.07 (18) |
C12—N1—C5—C1 | −0.9 (3) | C25—C26—C27—C28 | −0.3 (3) |
C2—C1—C5—N1 | 12.3 (3) | C26—C27—C28—C29 | −0.6 (3) |
C3—C1—C5—N1 | −108.6 (2) | C27—C28—C29—C24 | 0.1 (3) |
C4—C1—C5—N1 | 131.85 (19) | C27—C28—C29—C33 | 177.01 (18) |
C2—C1—C5—C6 | −165.54 (16) | C25—C24—C29—C28 | 1.4 (3) |
C3—C1—C5—C6 | 73.54 (19) | N2—C24—C29—C28 | 175.45 (16) |
C4—C1—C5—C6 | −46.0 (2) | C25—C24—C29—C33 | −175.49 (17) |
N1—C5—C6—C7 | 30.8 (3) | N2—C24—C29—C33 | −1.5 (3) |
C1—C5—C6—C7 | −151.06 (16) | C26—C25—C30—C31 | −20.9 (3) |
C24—N2—C7—C6 | −2.3 (3) | C24—C25—C30—C31 | 160.31 (17) |
C24—N2—C7—C8 | −175.07 (16) | C26—C25—C30—C32 | 103.5 (2) |
C5—C6—C7—N2 | 111.8 (2) | C24—C25—C30—C32 | −75.3 (2) |
C5—C6—C7—C8 | −75.8 (2) | C28—C29—C33—C34 | 29.1 (3) |
N2—C7—C8—C10 | 157.48 (16) | C24—C29—C33—C34 | −154.07 (18) |
C6—C7—C8—C10 | −15.4 (2) | C28—C29—C33—C35 | −95.5 (2) |
N2—C7—C8—C9 | −80.13 (19) | C24—C29—C33—C35 | 81.3 (2) |
C6—C7—C8—C9 | 106.97 (19) | C42—N3—C40—C41 | 9.2 (3) |
N2—C7—C8—C11 | 38.1 (2) | C42—N3—C40—C36 | 178.56 (16) |
C6—C7—C8—C11 | −134.76 (18) | C39—C36—C40—N3 | 142.66 (18) |
C5—N1—C12—C17 | 89.5 (2) | C37—C36—C40—N3 | 20.7 (2) |
C5—N1—C12—C13 | −98.8 (2) | C38—C36—C40—N3 | −96.9 (2) |
C17—C12—C13—C14 | −3.4 (2) | C39—C36—C40—C41 | −47.4 (2) |
N1—C12—C13—C14 | −175.06 (15) | C37—C36—C40—C41 | −169.35 (16) |
C17—C12—C13—C18 | 173.90 (15) | C38—C36—C40—C41 | 73.0 (2) |
N1—C12—C13—C18 | 2.3 (2) | N3—C40—C41—C40i | −120.68 (18) |
C12—C13—C14—C15 | 1.7 (3) | C36—C40—C41—C40i | 70.32 (14) |
C18—C13—C14—C15 | −175.68 (17) | C40—N3—C42—C47 | −73.6 (2) |
C13—C14—C15—C16 | 0.4 (3) | C40—N3—C42—C43 | 114.22 (19) |
C14—C15—C16—C17 | −0.8 (3) | C47—C42—C43—C44 | 5.7 (3) |
C15—C16—C17—C12 | −0.9 (3) | N3—C42—C43—C44 | 177.99 (15) |
C15—C16—C17—C21 | 177.67 (16) | C47—C42—C43—C48 | −169.53 (16) |
C13—C12—C17—C16 | 3.0 (2) | N3—C42—C43—C48 | 2.7 (2) |
N1—C12—C17—C16 | 174.57 (15) | C42—C43—C44—C45 | −2.3 (3) |
C13—C12—C17—C21 | −175.48 (15) | C48—C43—C44—C45 | 172.91 (17) |
N1—C12—C17—C21 | −3.9 (2) | C43—C44—C45—C46 | −1.3 (3) |
C14—C13—C18—C19 | −42.0 (2) | C44—C45—C46—C47 | 1.6 (3) |
C12—C13—C18—C19 | 140.75 (17) | C45—C46—C47—C42 | 1.7 (3) |
C14—C13—C18—C20 | 81.2 (2) | C45—C46—C47—C51 | −173.72 (17) |
C12—C13—C18—C20 | −96.1 (2) | C43—C42—C47—C46 | −5.4 (2) |
C16—C17—C21—C23 | −74.5 (2) | N3—C42—C47—C46 | −177.12 (15) |
C12—C17—C21—C23 | 103.95 (19) | C43—C42—C47—C51 | 170.00 (16) |
C16—C17—C21—C22 | 49.6 (2) | N3—C42—C47—C51 | −1.7 (3) |
C12—C17—C21—C22 | −131.89 (17) | C44—C43—C48—C49 | 32.5 (2) |
C7—N2—C24—C25 | −103.0 (2) | C42—C43—C48—C49 | −152.43 (17) |
C7—N2—C24—C29 | 82.8 (2) | C44—C43—C48—C50 | −92.6 (2) |
C29—C24—C25—C26 | −2.3 (3) | C42—C43—C48—C50 | 82.5 (2) |
N2—C24—C25—C26 | −176.36 (16) | C46—C47—C51—C52 | −28.7 (3) |
C29—C24—C25—C30 | 176.51 (17) | C42—C47—C51—C52 | 156.1 (2) |
N2—C24—C25—C30 | 2.5 (3) | C46—C47—C51—C53 | 95.9 (2) |
C24—C25—C26—C27 | 1.8 (3) | C42—C47—C51—C53 | −79.3 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C35H54N2 |
Mr | 502.80 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 41.471 (4), 9.3431 (9), 24.989 (3) |
β (°) | 102.077 (2) |
V (Å3) | 9468.0 (16) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.42 × 0.26 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.975, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33069, 8317, 5827 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.124, 1.02 |
No. of reflections | 8317 |
No. of parameters | 501 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.25 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999), SHELXTL.
N1—C5 | 1.270 (2) | C6—C7 | 1.509 (3) |
N1—C12 | 1.423 (2) | N3—C40 | 1.275 (2) |
N2—C7 | 1.283 (2) | N3—C42 | 1.416 (2) |
N2—C24 | 1.420 (2) | C40—C41 | 1.527 (2) |
C5—C6 | 1.530 (2) | ||
C5—N1—C12 | 128.60 (15) | N2—C7—C8 | 115.91 (15) |
C7—N2—C24 | 124.08 (15) | C6—C7—C8 | 121.23 (16) |
N1—C5—C6 | 117.63 (15) | C40—N3—C42 | 126.12 (15) |
N1—C5—C1 | 129.83 (15) | N3—C40—C41 | 124.14 (15) |
C6—C5—C1 | 112.51 (14) | N3—C40—C36 | 115.65 (15) |
C7—C6—C5 | 120.35 (16) | C41—C40—C36 | 119.37 (13) |
N2—C7—C6 | 122.46 (16) | C40—C41—C40i | 126.6 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
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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—N═C(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 C═N 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.