The title compound, C34H32N2, is formed as a result of the Diels-Alder reaction of N-benzylideneaniline and cyclohexen-2-one, catalyzed by zirconium tetrachloride. The molecule exists as the Z isomer. All three rings in the azabicyclo[2.2.2]octane system adopt boat conformations. The crystal packing is stabilized by van der Waals forces.
Supporting information
CCDC reference: 277243
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.03 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C28 - C33 .. 5.32 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C21 -C26 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
N-{3-(4-methylphenyl)-6-[(
Z)-(4-methylphenyl)methylidene]-2-phenyl- 2-azabicyclo[2.2.2]oct-5-ylidene}aniline
top
Crystal data top
C34H32N2 | F(000) = 1000 |
Mr = 468.62 | Dx = 1.174 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6129 reflections |
a = 14.1805 (8) Å | θ = 2.2–24.2° |
b = 10.1822 (5) Å | µ = 0.07 mm−1 |
c = 18.3636 (10) Å | T = 273 K |
β = 91.080 (1)° | Block, colourless |
V = 2651.0 (2) Å3 | 0.20 × 0.15 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3617 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −16→16 |
18613 measured reflections | k = −12→12 |
4659 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0649P)2 + 0.3061P] where P = (Fo2 + 2Fc2)/3 |
4659 reflections | (Δ/σ)max < 0.001 |
357 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.71505 (12) | 0.38772 (17) | 0.40618 (8) | 0.0734 (5) | |
H1 | 0.7604 | 0.3263 | 0.4284 | 0.071 (4)* | |
C3 | 0.66310 (10) | 0.48530 (14) | 0.28981 (7) | 0.0579 (4) | |
H3 | 0.6976 | 0.5588 | 0.2684 | 0.056 (4)* | |
C4 | 0.59598 (11) | 0.54247 (15) | 0.34694 (8) | 0.0651 (4) | |
H4 | 0.5499 | 0.6014 | 0.3236 | 0.071 (4)* | |
C5 | 0.54673 (12) | 0.42925 (15) | 0.38259 (7) | 0.0665 (4) | |
C6 | 0.61605 (12) | 0.33703 (16) | 0.41473 (7) | 0.0689 (4) | |
C7 | 0.72396 (15) | 0.52217 (19) | 0.44225 (9) | 0.0923 (6) | |
H7A | 0.7877 | 0.5552 | 0.4374 | 0.092 (5)* | |
H7B | 0.7105 | 0.5152 | 0.4937 | 0.100 (6)* | |
C8 | 0.65378 (15) | 0.61628 (19) | 0.40515 (10) | 0.0895 (6) | |
H8A | 0.6120 | 0.6528 | 0.4411 | 0.105 (6)* | |
H8B | 0.6876 | 0.6881 | 0.3828 | 0.089 (5)* | |
C9 | 0.82342 (10) | 0.39463 (13) | 0.30092 (8) | 0.0631 (4) | |
C10 | 0.90187 (13) | 0.36186 (16) | 0.34405 (11) | 0.0810 (5) | |
H10 | 0.8946 | 0.3441 | 0.3933 | 0.088 (6)* | |
C11 | 0.99038 (14) | 0.35556 (19) | 0.31406 (15) | 0.0991 (7) | |
H11 | 1.0418 | 0.3332 | 0.3437 | 0.114 (7)* | |
C12 | 1.00428 (15) | 0.3812 (2) | 0.24244 (15) | 0.1028 (7) | |
H12 | 1.0643 | 0.3766 | 0.2231 | 0.118 (7)* | |
C13 | 0.92841 (13) | 0.4138 (2) | 0.19973 (12) | 0.0933 (6) | |
H13 | 0.9370 | 0.4322 | 0.1507 | 0.124 (8)* | |
C14 | 0.83960 (12) | 0.42003 (16) | 0.22766 (9) | 0.0733 (4) | |
H14 | 0.7890 | 0.4417 | 0.1970 | 0.070 (4)* | |
C15 | 0.60893 (9) | 0.41726 (13) | 0.22888 (7) | 0.0540 (3) | |
C16 | 0.55872 (11) | 0.49098 (16) | 0.17852 (8) | 0.0710 (4) | |
H16 | 0.5603 | 0.5821 | 0.1817 | 0.089 (5)* | |
C17 | 0.50637 (12) | 0.4323 (2) | 0.12367 (9) | 0.0823 (5) | |
H17 | 0.4728 | 0.4846 | 0.0907 | 0.098 (6)* | |
C18 | 0.50268 (11) | 0.2980 (2) | 0.11656 (8) | 0.0766 (5) | |
C19 | 0.55261 (12) | 0.22529 (18) | 0.16675 (9) | 0.0798 (5) | |
H19 | 0.5514 | 0.1342 | 0.1634 | 0.096 (6)* | |
C20 | 0.60472 (11) | 0.28331 (15) | 0.22220 (8) | 0.0687 (4) | |
H20 | 0.6374 | 0.2308 | 0.2555 | 0.072 (4)* | |
C21 | 0.39163 (12) | 0.48831 (17) | 0.34999 (9) | 0.0724 (4) | |
C22 | 0.36100 (18) | 0.6039 (2) | 0.37983 (12) | 0.1000 (6) | |
H22 | 0.3895 | 0.6357 | 0.4223 | 0.113 (7)* | |
C23 | 0.2883 (2) | 0.6730 (3) | 0.34709 (19) | 0.1251 (9) | |
H23 | 0.2681 | 0.7518 | 0.3671 | 0.153 (10)* | |
C24 | 0.2460 (2) | 0.6256 (3) | 0.2854 (2) | 0.1343 (10) | |
H24 | 0.1944 | 0.6691 | 0.2648 | 0.173 (12)* | |
C25 | 0.27950 (19) | 0.5143 (3) | 0.25392 (17) | 0.1282 (9) | |
H25 | 0.2532 | 0.4852 | 0.2100 | 0.164 (11)* | |
C26 | 0.35083 (15) | 0.4457 (2) | 0.28599 (11) | 0.0962 (6) | |
H26 | 0.3723 | 0.3690 | 0.2644 | 0.121 (7)* | |
C27 | 0.58946 (12) | 0.22512 (16) | 0.44637 (7) | 0.0700 (4) | |
H27 | 0.5245 | 0.2141 | 0.4491 | 0.065 (4)* | |
C28 | 0.64467 (11) | 0.11731 (15) | 0.47740 (7) | 0.0661 (4) | |
C29 | 0.60943 (12) | 0.04931 (18) | 0.53685 (9) | 0.0748 (4) | |
H29 | 0.5524 | 0.0756 | 0.5564 | 0.093 (6)* | |
C30 | 0.65659 (12) | −0.05543 (18) | 0.56735 (9) | 0.0792 (5) | |
H30 | 0.6315 | −0.0973 | 0.6076 | 0.084 (5)* | |
C31 | 0.74014 (13) | −0.09967 (17) | 0.53953 (9) | 0.0773 (5) | |
C32 | 0.77434 (14) | −0.0349 (2) | 0.47935 (10) | 0.0858 (5) | |
H32 | 0.8302 | −0.0636 | 0.4589 | 0.090 (6)* | |
C33 | 0.72795 (13) | 0.07119 (18) | 0.44891 (9) | 0.0777 (5) | |
H33 | 0.7531 | 0.1125 | 0.4085 | 0.089 (5)* | |
C34 | 0.79197 (18) | −0.2143 (2) | 0.57324 (14) | 0.1087 (7) | |
H34A | 0.8396 | −0.2442 | 0.5407 | 0.148 (10)* | |
H34B | 0.7483 | −0.2844 | 0.5820 | 0.179 (12)* | |
H34C | 0.8210 | −0.1875 | 0.6185 | 0.162 (11)* | |
C35 | 0.44783 (17) | 0.2326 (3) | 0.05490 (13) | 0.1189 (8) | |
H35A | 0.4858 | 0.2301 | 0.0122 | 0.193 (13)* | |
H35B | 0.3913 | 0.2815 | 0.0446 | 0.173 (12)* | |
H35C | 0.4316 | 0.1446 | 0.0688 | 0.210 (17)* | |
N2 | 0.73230 (8) | 0.40051 (12) | 0.32742 (6) | 0.0629 (3) | |
N3 | 0.45867 (11) | 0.40624 (14) | 0.38483 (7) | 0.0797 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0849 (11) | 0.0818 (11) | 0.0528 (8) | −0.0278 (9) | −0.0132 (7) | 0.0146 (7) |
C3 | 0.0686 (8) | 0.0531 (8) | 0.0522 (8) | −0.0080 (6) | 0.0026 (6) | 0.0070 (6) |
C4 | 0.0809 (10) | 0.0593 (8) | 0.0553 (8) | −0.0107 (8) | 0.0074 (7) | −0.0026 (7) |
C5 | 0.0833 (11) | 0.0715 (10) | 0.0448 (7) | −0.0189 (8) | 0.0029 (7) | −0.0013 (7) |
C6 | 0.0850 (10) | 0.0774 (10) | 0.0441 (7) | −0.0252 (8) | −0.0051 (7) | 0.0064 (7) |
C7 | 0.1166 (15) | 0.1046 (14) | 0.0552 (9) | −0.0513 (12) | −0.0074 (9) | −0.0016 (9) |
C8 | 0.1159 (15) | 0.0820 (12) | 0.0711 (11) | −0.0306 (11) | 0.0104 (11) | −0.0175 (9) |
C9 | 0.0675 (9) | 0.0499 (8) | 0.0714 (9) | −0.0096 (7) | −0.0100 (7) | 0.0051 (7) |
C10 | 0.0787 (11) | 0.0685 (10) | 0.0948 (13) | −0.0097 (8) | −0.0202 (9) | 0.0200 (9) |
C11 | 0.0738 (12) | 0.0763 (12) | 0.146 (2) | 0.0026 (9) | −0.0267 (13) | 0.0174 (12) |
C12 | 0.0712 (13) | 0.0964 (14) | 0.141 (2) | 0.0080 (10) | 0.0126 (13) | 0.0024 (14) |
C13 | 0.0748 (12) | 0.1072 (15) | 0.0983 (14) | 0.0059 (10) | 0.0137 (10) | −0.0013 (11) |
C14 | 0.0686 (10) | 0.0804 (11) | 0.0708 (10) | 0.0022 (8) | −0.0008 (8) | 0.0032 (8) |
C15 | 0.0593 (8) | 0.0553 (8) | 0.0475 (7) | 0.0035 (6) | 0.0035 (6) | 0.0042 (6) |
C16 | 0.0874 (11) | 0.0658 (10) | 0.0598 (9) | 0.0124 (8) | −0.0015 (8) | 0.0074 (7) |
C17 | 0.0844 (11) | 0.1038 (14) | 0.0584 (9) | 0.0213 (10) | −0.0123 (8) | 0.0080 (9) |
C18 | 0.0645 (9) | 0.1054 (14) | 0.0598 (9) | 0.0044 (9) | −0.0044 (7) | −0.0124 (9) |
C19 | 0.0863 (11) | 0.0686 (11) | 0.0841 (11) | 0.0009 (8) | −0.0117 (9) | −0.0154 (9) |
C20 | 0.0780 (10) | 0.0582 (9) | 0.0691 (9) | 0.0066 (7) | −0.0156 (8) | 0.0016 (7) |
C21 | 0.0765 (10) | 0.0773 (11) | 0.0639 (9) | −0.0156 (8) | 0.0099 (8) | 0.0072 (8) |
C22 | 0.1258 (17) | 0.0968 (15) | 0.0784 (12) | −0.0113 (13) | 0.0287 (12) | −0.0152 (11) |
C23 | 0.122 (2) | 0.0964 (17) | 0.158 (2) | 0.0202 (16) | 0.0497 (19) | 0.0005 (17) |
C24 | 0.1055 (19) | 0.108 (2) | 0.189 (3) | 0.0154 (15) | −0.0125 (19) | 0.021 (2) |
C25 | 0.138 (2) | 0.0979 (17) | 0.147 (2) | 0.0088 (15) | −0.0525 (18) | 0.0029 (16) |
C26 | 0.1128 (15) | 0.0790 (12) | 0.0960 (14) | 0.0035 (11) | −0.0224 (12) | −0.0080 (11) |
C27 | 0.0784 (10) | 0.0813 (11) | 0.0502 (8) | −0.0228 (8) | −0.0017 (7) | 0.0057 (7) |
C28 | 0.0726 (9) | 0.0760 (10) | 0.0497 (8) | −0.0229 (8) | −0.0022 (7) | 0.0016 (7) |
C29 | 0.0715 (10) | 0.0875 (11) | 0.0656 (9) | −0.0134 (9) | 0.0037 (8) | 0.0165 (8) |
C30 | 0.0816 (11) | 0.0902 (12) | 0.0656 (10) | −0.0198 (10) | −0.0028 (8) | 0.0183 (9) |
C31 | 0.0827 (11) | 0.0774 (11) | 0.0714 (10) | −0.0136 (9) | −0.0098 (9) | −0.0033 (8) |
C32 | 0.0819 (12) | 0.0943 (13) | 0.0813 (12) | −0.0099 (10) | 0.0094 (9) | −0.0127 (10) |
C33 | 0.0920 (12) | 0.0850 (12) | 0.0564 (9) | −0.0214 (10) | 0.0090 (8) | −0.0004 (8) |
C34 | 0.1186 (17) | 0.0925 (15) | 0.1142 (17) | 0.0075 (14) | −0.0148 (15) | 0.0029 (13) |
C35 | 0.0978 (16) | 0.170 (3) | 0.0876 (15) | −0.0107 (17) | −0.0220 (12) | −0.0353 (15) |
N2 | 0.0664 (7) | 0.0692 (8) | 0.0527 (6) | −0.0119 (6) | −0.0084 (5) | 0.0115 (6) |
N3 | 0.0843 (10) | 0.0897 (10) | 0.0652 (8) | −0.0220 (8) | 0.0008 (7) | 0.0135 (7) |
Geometric parameters (Å, º) top
C1—N2 | 1.4770 (19) | C18—C19 | 1.369 (2) |
C1—C6 | 1.507 (2) | C18—C35 | 1.516 (2) |
C1—C7 | 1.525 (2) | C19—C20 | 1.380 (2) |
C1—H1 | 0.9800 | C19—H19 | 0.9300 |
C3—N2 | 1.4695 (18) | C20—H20 | 0.9300 |
C3—C15 | 1.5132 (19) | C21—C26 | 1.371 (2) |
C3—C4 | 1.544 (2) | C21—C22 | 1.372 (3) |
C3—H3 | 0.9800 | C21—N3 | 1.410 (2) |
C4—C5 | 1.504 (2) | C22—C23 | 1.377 (3) |
C4—C8 | 1.532 (2) | C22—H22 | 0.9300 |
C4—H4 | 0.9800 | C23—C24 | 1.359 (4) |
C5—N3 | 1.272 (2) | C23—H23 | 0.9300 |
C5—C6 | 1.475 (2) | C24—C25 | 1.362 (4) |
C6—C27 | 1.337 (2) | C24—H24 | 0.9300 |
C7—C8 | 1.532 (3) | C25—C26 | 1.355 (3) |
C7—H7A | 0.9700 | C25—H25 | 0.9300 |
C7—H7B | 0.9700 | C26—H26 | 0.9300 |
C8—H8A | 0.9700 | C27—C28 | 1.458 (2) |
C8—H8B | 0.9700 | C27—H27 | 0.9300 |
C9—N2 | 1.3907 (19) | C28—C33 | 1.383 (2) |
C9—C14 | 1.393 (2) | C28—C29 | 1.393 (2) |
C9—C10 | 1.394 (2) | C29—C30 | 1.373 (2) |
C10—C11 | 1.382 (3) | C29—H29 | 0.9300 |
C10—H10 | 0.9300 | C30—C31 | 1.375 (2) |
C11—C12 | 1.359 (3) | C30—H30 | 0.9300 |
C11—H11 | 0.9300 | C31—C32 | 1.383 (2) |
C12—C13 | 1.361 (3) | C31—C34 | 1.506 (3) |
C12—H12 | 0.9300 | C32—C33 | 1.377 (3) |
C13—C14 | 1.370 (2) | C32—H32 | 0.9300 |
C13—H13 | 0.9300 | C33—H33 | 0.9300 |
C14—H14 | 0.9300 | C34—H34A | 0.9600 |
C15—C20 | 1.371 (2) | C34—H34B | 0.9600 |
C15—C16 | 1.3787 (19) | C34—H34C | 0.9600 |
C16—C17 | 1.376 (2) | C35—H35A | 0.9600 |
C16—H16 | 0.9300 | C35—H35B | 0.9600 |
C17—C18 | 1.375 (3) | C35—H35C | 0.9600 |
C17—H17 | 0.9300 | | |
| | | |
N2—C1—C6 | 107.70 (11) | C19—C18—C35 | 121.1 (2) |
N2—C1—C7 | 109.41 (12) | C17—C18—C35 | 121.74 (19) |
C6—C1—C7 | 109.39 (16) | C18—C19—C20 | 121.90 (16) |
N2—C1—H1 | 110.1 | C18—C19—H19 | 119.1 |
C6—C1—H1 | 110.1 | C20—C19—H19 | 119.1 |
C7—C1—H1 | 110.1 | C15—C20—C19 | 120.93 (14) |
N2—C3—C15 | 113.82 (11) | C15—C20—H20 | 119.5 |
N2—C3—C4 | 108.47 (11) | C19—C20—H20 | 119.5 |
C15—C3—C4 | 111.36 (11) | C26—C21—C22 | 118.8 (2) |
N2—C3—H3 | 107.7 | C26—C21—N3 | 118.13 (16) |
C15—C3—H3 | 107.7 | C22—C21—N3 | 122.88 (18) |
C4—C3—H3 | 107.7 | C21—C22—C23 | 120.2 (2) |
C5—C4—C8 | 108.61 (13) | C21—C22—H22 | 119.9 |
C5—C4—C3 | 107.70 (12) | C23—C22—H22 | 119.9 |
C8—C4—C3 | 109.31 (13) | C24—C23—C22 | 119.8 (2) |
C5—C4—H4 | 110.4 | C24—C23—H23 | 120.1 |
C8—C4—H4 | 110.4 | C22—C23—H23 | 120.1 |
C3—C4—H4 | 110.4 | C23—C24—C25 | 119.8 (3) |
N3—C5—C6 | 121.14 (14) | C23—C24—H24 | 120.1 |
N3—C5—C4 | 128.27 (15) | C25—C24—H24 | 120.1 |
C6—C5—C4 | 110.53 (14) | C26—C25—C24 | 120.5 (3) |
C27—C6—C5 | 121.70 (15) | C26—C25—H25 | 119.7 |
C27—C6—C1 | 127.47 (16) | C24—C25—H25 | 119.7 |
C5—C6—C1 | 110.83 (13) | C25—C26—C21 | 120.6 (2) |
C1—C7—C8 | 108.69 (14) | C25—C26—H26 | 119.7 |
C1—C7—H7A | 110.0 | C21—C26—H26 | 119.7 |
C8—C7—H7A | 110.0 | C6—C27—C28 | 131.14 (16) |
C1—C7—H7B | 110.0 | C6—C27—H27 | 114.4 |
C8—C7—H7B | 110.0 | C28—C27—H27 | 114.4 |
H7A—C7—H7B | 108.3 | C33—C28—C29 | 116.69 (16) |
C4—C8—C7 | 109.76 (15) | C33—C28—C27 | 124.33 (14) |
C4—C8—H8A | 109.7 | C29—C28—C27 | 118.84 (15) |
C7—C8—H8A | 109.7 | C30—C29—C28 | 121.78 (17) |
C4—C8—H8B | 109.7 | C30—C29—H29 | 119.1 |
C7—C8—H8B | 109.7 | C28—C29—H29 | 119.1 |
H8A—C8—H8B | 108.2 | C29—C30—C31 | 121.30 (16) |
N2—C9—C14 | 120.06 (13) | C29—C30—H30 | 119.4 |
N2—C9—C10 | 123.26 (15) | C31—C30—H30 | 119.4 |
C14—C9—C10 | 116.68 (16) | C30—C31—C32 | 117.27 (17) |
C11—C10—C9 | 120.40 (19) | C30—C31—C34 | 121.22 (18) |
C11—C10—H10 | 119.8 | C32—C31—C34 | 121.50 (19) |
C9—C10—H10 | 119.8 | C33—C32—C31 | 121.77 (18) |
C12—C11—C10 | 121.75 (18) | C33—C32—H32 | 119.1 |
C12—C11—H11 | 119.1 | C31—C32—H32 | 119.1 |
C10—C11—H11 | 119.1 | C32—C33—C28 | 121.16 (15) |
C11—C12—C13 | 118.51 (19) | C32—C33—H33 | 119.4 |
C11—C12—H12 | 120.7 | C28—C33—H33 | 119.4 |
C13—C12—H12 | 120.7 | C31—C34—H34A | 109.5 |
C12—C13—C14 | 121.2 (2) | C31—C34—H34B | 109.5 |
C12—C13—H13 | 119.4 | H34A—C34—H34B | 109.5 |
C14—C13—H13 | 119.4 | C31—C34—H34C | 109.5 |
C13—C14—C9 | 121.47 (17) | H34A—C34—H34C | 109.5 |
C13—C14—H14 | 119.3 | H34B—C34—H34C | 109.5 |
C9—C14—H14 | 119.3 | C18—C35—H35A | 109.5 |
C20—C15—C16 | 117.43 (14) | C18—C35—H35B | 109.5 |
C20—C15—C3 | 122.85 (12) | H35A—C35—H35B | 109.5 |
C16—C15—C3 | 119.69 (13) | C18—C35—H35C | 109.5 |
C17—C16—C15 | 121.27 (16) | H35A—C35—H35C | 109.5 |
C17—C16—H16 | 119.4 | H35B—C35—H35C | 109.5 |
C15—C16—H16 | 119.4 | C9—N2—C3 | 118.52 (11) |
C18—C17—C16 | 121.36 (15) | C9—N2—C1 | 120.73 (12) |
C18—C17—H17 | 119.3 | C3—N2—C1 | 112.99 (12) |
C16—C17—H17 | 119.3 | C5—N3—C21 | 122.00 (13) |
C19—C18—C17 | 117.11 (15) | | |
| | | |
N2—C3—C4—C5 | −60.88 (15) | C3—C15—C20—C19 | 178.44 (14) |
C15—C3—C4—C5 | 65.12 (15) | C18—C19—C20—C15 | −0.4 (3) |
N2—C3—C4—C8 | 56.94 (16) | C26—C21—C22—C23 | 2.2 (3) |
C15—C3—C4—C8 | −177.06 (12) | N3—C21—C22—C23 | −173.09 (18) |
C8—C4—C5—N3 | 120.97 (18) | C21—C22—C23—C24 | 0.7 (4) |
C3—C4—C5—N3 | −120.76 (17) | C22—C23—C24—C25 | −3.9 (4) |
C8—C4—C5—C6 | −61.56 (16) | C23—C24—C25—C26 | 4.2 (4) |
C3—C4—C5—C6 | 56.71 (15) | C24—C25—C26—C21 | −1.2 (4) |
N3—C5—C6—C27 | 1.0 (2) | C22—C21—C26—C25 | −2.0 (3) |
C4—C5—C6—C27 | −176.64 (13) | N3—C21—C26—C25 | 173.5 (2) |
N3—C5—C6—C1 | −178.95 (14) | C5—C6—C27—C28 | 175.92 (14) |
C4—C5—C6—C1 | 3.36 (17) | C1—C6—C27—C28 | −4.1 (3) |
N2—C1—C6—C27 | 119.23 (16) | C6—C27—C28—C33 | −37.1 (2) |
C7—C1—C6—C27 | −121.95 (18) | C6—C27—C28—C29 | 147.31 (17) |
N2—C1—C6—C5 | −60.78 (17) | C33—C28—C29—C30 | 2.2 (2) |
C7—C1—C6—C5 | 58.04 (16) | C27—C28—C29—C30 | 178.16 (15) |
N2—C1—C7—C8 | 57.59 (19) | C28—C29—C30—C31 | −1.3 (3) |
C6—C1—C7—C8 | −60.17 (17) | C29—C30—C31—C32 | −0.4 (2) |
C5—C4—C8—C7 | 57.61 (18) | C29—C30—C31—C34 | 179.78 (17) |
C3—C4—C8—C7 | −59.63 (17) | C30—C31—C32—C33 | 1.1 (3) |
C1—C7—C8—C4 | 2.33 (19) | C34—C31—C32—C33 | −179.08 (18) |
N2—C9—C10—C11 | 178.88 (15) | C31—C32—C33—C28 | −0.1 (3) |
C14—C9—C10—C11 | 0.0 (2) | C29—C28—C33—C32 | −1.5 (2) |
C9—C10—C11—C12 | 0.3 (3) | C27—C28—C33—C32 | −177.21 (15) |
C10—C11—C12—C13 | 0.0 (3) | C14—C9—N2—C3 | −26.36 (19) |
C11—C12—C13—C14 | −0.4 (3) | C10—C9—N2—C3 | 154.75 (14) |
C12—C13—C14—C9 | 0.7 (3) | C14—C9—N2—C1 | −173.51 (14) |
N2—C9—C14—C13 | −179.37 (15) | C10—C9—N2—C1 | 7.6 (2) |
C10—C9—C14—C13 | −0.4 (2) | C15—C3—N2—C9 | 89.35 (15) |
N2—C3—C15—C20 | 17.26 (19) | C4—C3—N2—C9 | −146.09 (12) |
C4—C3—C15—C20 | −105.73 (16) | C15—C3—N2—C1 | −121.08 (12) |
N2—C3—C15—C16 | −164.80 (12) | C4—C3—N2—C1 | 3.48 (15) |
C4—C3—C15—C16 | 72.21 (16) | C6—C1—N2—C9 | −154.66 (13) |
C20—C15—C16—C17 | 0.0 (2) | C7—C1—N2—C9 | 86.53 (18) |
C3—C15—C16—C17 | −178.04 (14) | C6—C1—N2—C3 | 56.53 (16) |
C15—C16—C17—C18 | −0.5 (3) | C7—C1—N2—C3 | −62.29 (17) |
C16—C17—C18—C19 | 0.6 (3) | C6—C5—N3—C21 | −175.42 (14) |
C16—C17—C18—C35 | −177.96 (18) | C4—C5—N3—C21 | 1.8 (2) |
C17—C18—C19—C20 | −0.1 (3) | C26—C21—N3—C5 | 103.9 (2) |
C35—C18—C19—C20 | 178.44 (18) | C22—C21—N3—C5 | −80.8 (2) |
C16—C15—C20—C19 | 0.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20···N2 | 0.93 | 2.54 | 2.881 (2) | 102 |
C27—H27···N3 | 0.93 | 2.46 | 2.835 (2) | 104 |