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In the title compound, C
27H
25NO, all three rings in the azabicyclo[2.2.2]octane unit adopt a boat conformation. An intermolecular C—H
O interaction forms a characteristic
R22(14) motif dimer in the crystal packing.
Supporting information
CCDC reference: 640287
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.108
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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: DIAMOND (Brandenburg & Putz, 2005) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
(3
Z)-2-Benzyl-3-benzylidene-6-phenyl-2-azabicyclo[2.2.2]octan-5-one
top
Crystal data top
C27H25NO | F(000) = 808 |
Mr = 379.48 | Dx = 1.218 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7271 reflections |
a = 9.5155 (7) Å | θ = 2.3–25.1° |
b = 17.6544 (13) Å | µ = 0.07 mm−1 |
c = 12.4242 (9) Å | T = 293 K |
β = 97.464 (1)° | Block, colorless |
V = 2069.5 (3) Å3 | 0.19 × 0.14 × 0.11 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3121 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −11→11 |
19631 measured reflections | k = −20→20 |
3639 independent reflections | l = −14→14 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3 |
3639 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 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 | 0.76411 (16) | 0.18454 (8) | 0.71092 (12) | 0.0516 (4) | |
H1 | 0.8671 | 0.1855 | 0.7315 | 0.062* | |
C2 | 0.72152 (18) | 0.10155 (9) | 0.68501 (13) | 0.0603 (4) | |
H2 | 0.7631 | 0.0837 | 0.6215 | 0.072* | |
C3 | 0.77793 (18) | 0.05664 (9) | 0.78422 (14) | 0.0625 (4) | |
C4 | 0.71438 (15) | 0.08203 (8) | 0.88117 (12) | 0.0520 (4) | |
C5 | 0.61838 (14) | 0.14911 (8) | 0.85152 (11) | 0.0483 (3) | |
H5 | 0.5796 | 0.1675 | 0.9160 | 0.058* | |
C6 | 0.49826 (16) | 0.12584 (10) | 0.76485 (13) | 0.0604 (4) | |
H6A | 0.4385 | 0.1692 | 0.7437 | 0.072* | |
H6B | 0.4405 | 0.0873 | 0.7935 | 0.072* | |
C7 | 0.56021 (19) | 0.09474 (10) | 0.66585 (14) | 0.0674 (4) | |
H7A | 0.5333 | 0.0421 | 0.6544 | 0.081* | |
H7B | 0.5231 | 0.1231 | 0.6015 | 0.081* | |
C8 | 0.73004 (15) | 0.23761 (8) | 0.61496 (11) | 0.0500 (3) | |
C9 | 0.79588 (17) | 0.22761 (10) | 0.52298 (13) | 0.0609 (4) | |
H9 | 0.8575 | 0.1870 | 0.5195 | 0.073* | |
C10 | 0.77167 (19) | 0.27671 (11) | 0.43677 (13) | 0.0689 (5) | |
H10 | 0.8158 | 0.2687 | 0.3752 | 0.083* | |
C11 | 0.68247 (19) | 0.33765 (10) | 0.44111 (13) | 0.0675 (5) | |
H11 | 0.6674 | 0.3714 | 0.3833 | 0.081* | |
C12 | 0.61632 (17) | 0.34804 (9) | 0.53119 (13) | 0.0622 (4) | |
H12 | 0.5556 | 0.3890 | 0.5344 | 0.075* | |
C13 | 0.63875 (16) | 0.29835 (8) | 0.61749 (12) | 0.0548 (4) | |
H13 | 0.5920 | 0.3058 | 0.6779 | 0.066* | |
C14 | 0.80089 (16) | 0.24824 (9) | 0.88608 (12) | 0.0573 (4) | |
H14A | 0.8654 | 0.2776 | 0.8482 | 0.069* | |
H14B | 0.8563 | 0.2103 | 0.9293 | 0.069* | |
C15 | 0.73330 (15) | 0.29988 (8) | 0.96063 (12) | 0.0517 (4) | |
C16 | 0.69091 (19) | 0.37183 (9) | 0.92757 (14) | 0.0687 (5) | |
H16 | 0.7011 | 0.3877 | 0.8576 | 0.082* | |
C17 | 0.6338 (2) | 0.42032 (10) | 0.99665 (18) | 0.0818 (6) | |
H17 | 0.6075 | 0.4690 | 0.9736 | 0.098* | |
C18 | 0.61515 (19) | 0.39747 (11) | 1.09925 (16) | 0.0763 (5) | |
H18 | 0.5762 | 0.4303 | 1.1459 | 0.092* | |
C19 | 0.65444 (18) | 0.32583 (11) | 1.13233 (13) | 0.0688 (5) | |
H19 | 0.6405 | 0.3095 | 1.2013 | 0.083* | |
C20 | 0.71440 (16) | 0.27776 (9) | 1.06415 (12) | 0.0587 (4) | |
H20 | 0.7426 | 0.2296 | 1.0882 | 0.070* | |
C21 | 0.75045 (16) | 0.04972 (8) | 0.97775 (13) | 0.0574 (4) | |
H21 | 0.8182 | 0.0116 | 0.9803 | 0.069* | |
C22 | 0.69700 (16) | 0.06670 (8) | 1.08043 (13) | 0.0544 (4) | |
C23 | 0.78968 (19) | 0.06525 (10) | 1.17672 (14) | 0.0703 (5) | |
H23 | 0.8835 | 0.0508 | 1.1756 | 0.084* | |
C24 | 0.7441 (2) | 0.08488 (12) | 1.27331 (16) | 0.0843 (6) | |
H24 | 0.8079 | 0.0852 | 1.3367 | 0.101* | |
C25 | 0.6052 (2) | 0.10399 (11) | 1.27717 (16) | 0.0818 (6) | |
H25 | 0.5751 | 0.1175 | 1.3428 | 0.098* | |
C26 | 0.5109 (2) | 0.10300 (10) | 1.18361 (15) | 0.0713 (5) | |
H26 | 0.4162 | 0.1148 | 1.1861 | 0.086* | |
C27 | 0.55611 (17) | 0.08461 (9) | 1.08638 (13) | 0.0586 (4) | |
H27 | 0.4914 | 0.0841 | 1.0235 | 0.070* | |
N1 | 0.69867 (12) | 0.20996 (6) | 0.80599 (9) | 0.0483 (3) | |
O1 | 0.86636 (15) | 0.00683 (7) | 0.78421 (11) | 0.0900 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0503 (8) | 0.0527 (8) | 0.0534 (8) | 0.0070 (6) | 0.0124 (6) | −0.0004 (6) |
C2 | 0.0763 (11) | 0.0504 (9) | 0.0576 (9) | 0.0088 (8) | 0.0212 (8) | −0.0048 (7) |
C3 | 0.0692 (10) | 0.0471 (9) | 0.0749 (11) | 0.0099 (8) | 0.0232 (8) | 0.0011 (8) |
C4 | 0.0527 (8) | 0.0437 (8) | 0.0609 (9) | 0.0027 (6) | 0.0127 (7) | 0.0031 (7) |
C5 | 0.0486 (8) | 0.0483 (8) | 0.0494 (8) | 0.0052 (6) | 0.0116 (6) | 0.0010 (6) |
C6 | 0.0552 (9) | 0.0616 (10) | 0.0636 (10) | 0.0005 (7) | 0.0049 (7) | −0.0021 (8) |
C7 | 0.0823 (12) | 0.0582 (10) | 0.0614 (10) | −0.0095 (8) | 0.0080 (8) | −0.0081 (8) |
C8 | 0.0488 (8) | 0.0514 (8) | 0.0504 (8) | −0.0037 (6) | 0.0082 (6) | −0.0013 (6) |
C9 | 0.0601 (9) | 0.0673 (10) | 0.0571 (9) | 0.0019 (8) | 0.0144 (7) | −0.0012 (8) |
C10 | 0.0758 (11) | 0.0819 (12) | 0.0511 (9) | −0.0109 (10) | 0.0164 (8) | 0.0017 (8) |
C11 | 0.0797 (12) | 0.0651 (11) | 0.0554 (10) | −0.0124 (9) | −0.0003 (8) | 0.0095 (8) |
C12 | 0.0664 (10) | 0.0524 (9) | 0.0657 (10) | −0.0005 (7) | 0.0005 (8) | 0.0041 (8) |
C13 | 0.0576 (9) | 0.0527 (8) | 0.0549 (9) | 0.0000 (7) | 0.0100 (7) | −0.0009 (7) |
C14 | 0.0541 (8) | 0.0562 (9) | 0.0622 (9) | −0.0009 (7) | 0.0096 (7) | −0.0032 (7) |
C15 | 0.0515 (8) | 0.0493 (8) | 0.0532 (8) | −0.0034 (6) | 0.0031 (6) | −0.0028 (7) |
C16 | 0.0857 (12) | 0.0546 (9) | 0.0681 (11) | 0.0031 (8) | 0.0187 (9) | 0.0061 (8) |
C17 | 0.0956 (14) | 0.0512 (10) | 0.1017 (15) | 0.0095 (9) | 0.0242 (12) | −0.0048 (10) |
C18 | 0.0711 (11) | 0.0761 (13) | 0.0835 (13) | −0.0043 (9) | 0.0165 (10) | −0.0312 (10) |
C19 | 0.0686 (10) | 0.0866 (13) | 0.0501 (9) | −0.0093 (9) | 0.0036 (8) | −0.0114 (9) |
C20 | 0.0623 (9) | 0.0583 (9) | 0.0528 (9) | −0.0017 (7) | −0.0025 (7) | 0.0001 (7) |
C21 | 0.0569 (9) | 0.0438 (8) | 0.0726 (10) | 0.0070 (7) | 0.0122 (8) | 0.0075 (7) |
C22 | 0.0602 (9) | 0.0410 (8) | 0.0618 (9) | 0.0031 (6) | 0.0078 (7) | 0.0116 (7) |
C23 | 0.0696 (11) | 0.0677 (11) | 0.0716 (11) | 0.0134 (9) | 0.0018 (9) | 0.0163 (9) |
C24 | 0.1012 (15) | 0.0853 (13) | 0.0621 (11) | 0.0124 (11) | −0.0056 (10) | 0.0093 (9) |
C25 | 0.1064 (16) | 0.0762 (12) | 0.0653 (11) | 0.0123 (11) | 0.0208 (11) | 0.0043 (9) |
C26 | 0.0726 (11) | 0.0681 (11) | 0.0767 (12) | 0.0061 (9) | 0.0225 (9) | 0.0090 (9) |
C27 | 0.0589 (9) | 0.0550 (9) | 0.0622 (10) | −0.0021 (7) | 0.0087 (7) | 0.0094 (7) |
N1 | 0.0520 (7) | 0.0458 (6) | 0.0483 (6) | 0.0037 (5) | 0.0110 (5) | −0.0005 (5) |
O1 | 0.1083 (10) | 0.0706 (8) | 0.0984 (10) | 0.0417 (8) | 0.0415 (8) | 0.0118 (7) |
Geometric parameters (Å, º) top
C1—N1 | 1.4750 (17) | C13—H13 | 0.9300 |
C1—C8 | 1.518 (2) | C14—N1 | 1.4633 (18) |
C1—C2 | 1.543 (2) | C14—C15 | 1.502 (2) |
C1—H1 | 0.9800 | C14—H14A | 0.9700 |
C2—C3 | 1.505 (2) | C14—H14B | 0.9700 |
C2—C7 | 1.527 (2) | C15—C20 | 1.378 (2) |
C2—H2 | 0.9800 | C15—C16 | 1.379 (2) |
C3—O1 | 1.2171 (19) | C16—C17 | 1.373 (2) |
C3—C4 | 1.485 (2) | C16—H16 | 0.9300 |
C4—C21 | 1.333 (2) | C17—C18 | 1.370 (3) |
C4—C5 | 1.5116 (19) | C17—H17 | 0.9300 |
C5—N1 | 1.4732 (18) | C18—C19 | 1.367 (3) |
C5—C6 | 1.522 (2) | C18—H18 | 0.9300 |
C5—H5 | 0.9800 | C19—C20 | 1.374 (2) |
C6—C7 | 1.533 (2) | C19—H19 | 0.9300 |
C6—H6A | 0.9700 | C20—H20 | 0.9300 |
C6—H6B | 0.9700 | C21—C22 | 1.464 (2) |
C7—H7A | 0.9700 | C21—H21 | 0.9300 |
C7—H7B | 0.9700 | C22—C27 | 1.389 (2) |
C8—C13 | 1.383 (2) | C22—C23 | 1.391 (2) |
C8—C9 | 1.384 (2) | C23—C24 | 1.373 (3) |
C9—C10 | 1.374 (2) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—C25 | 1.370 (3) |
C10—C11 | 1.376 (3) | C24—H24 | 0.9300 |
C10—H10 | 0.9300 | C25—C26 | 1.373 (3) |
C11—C12 | 1.366 (2) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—C27 | 1.373 (2) |
C12—C13 | 1.380 (2) | C26—H26 | 0.9300 |
C12—H12 | 0.9300 | C27—H27 | 0.9300 |
| | | |
N1—C1—C8 | 111.83 (11) | C12—C13—C8 | 120.61 (15) |
N1—C1—C2 | 109.22 (12) | C12—C13—H13 | 119.7 |
C8—C1—C2 | 113.50 (12) | C8—C13—H13 | 119.7 |
N1—C1—H1 | 107.3 | N1—C14—C15 | 113.54 (12) |
C8—C1—H1 | 107.3 | N1—C14—H14A | 108.9 |
C2—C1—H1 | 107.3 | C15—C14—H14A | 108.9 |
C3—C2—C7 | 109.30 (14) | N1—C14—H14B | 108.9 |
C3—C2—C1 | 105.86 (13) | C15—C14—H14B | 108.9 |
C7—C2—C1 | 109.80 (13) | H14A—C14—H14B | 107.7 |
C3—C2—H2 | 110.6 | C20—C15—C16 | 118.06 (15) |
C7—C2—H2 | 110.6 | C20—C15—C14 | 121.44 (14) |
C1—C2—H2 | 110.6 | C16—C15—C14 | 120.49 (14) |
O1—C3—C4 | 124.92 (16) | C17—C16—C15 | 120.81 (17) |
O1—C3—C2 | 123.61 (15) | C17—C16—H16 | 119.6 |
C4—C3—C2 | 111.46 (13) | C15—C16—H16 | 119.6 |
C21—C4—C3 | 121.10 (14) | C18—C17—C16 | 120.49 (17) |
C21—C4—C5 | 129.16 (14) | C18—C17—H17 | 119.8 |
C3—C4—C5 | 109.61 (13) | C16—C17—H17 | 119.8 |
N1—C5—C4 | 109.74 (11) | C19—C18—C17 | 119.26 (16) |
N1—C5—C6 | 107.73 (11) | C19—C18—H18 | 120.4 |
C4—C5—C6 | 109.61 (12) | C17—C18—H18 | 120.4 |
N1—C5—H5 | 109.9 | C18—C19—C20 | 120.35 (17) |
C4—C5—H5 | 109.9 | C18—C19—H19 | 119.8 |
C6—C5—H5 | 109.9 | C20—C19—H19 | 119.8 |
C5—C6—C7 | 109.43 (13) | C19—C20—C15 | 121.01 (16) |
C5—C6—H6A | 109.8 | C19—C20—H20 | 119.5 |
C7—C6—H6A | 109.8 | C15—C20—H20 | 119.5 |
C5—C6—H6B | 109.8 | C4—C21—C22 | 128.23 (14) |
C7—C6—H6B | 109.8 | C4—C21—H21 | 115.9 |
H6A—C6—H6B | 108.2 | C22—C21—H21 | 115.9 |
C2—C7—C6 | 109.28 (13) | C27—C22—C23 | 117.83 (15) |
C2—C7—H7A | 109.8 | C27—C22—C21 | 122.68 (14) |
C6—C7—H7A | 109.8 | C23—C22—C21 | 119.49 (15) |
C2—C7—H7B | 109.8 | C24—C23—C22 | 120.67 (17) |
C6—C7—H7B | 109.8 | C24—C23—H23 | 119.7 |
H7A—C7—H7B | 108.3 | C22—C23—H23 | 119.7 |
C13—C8—C9 | 118.09 (14) | C25—C24—C23 | 120.57 (18) |
C13—C8—C1 | 122.10 (13) | C25—C24—H24 | 119.7 |
C9—C8—C1 | 119.76 (13) | C23—C24—H24 | 119.7 |
C10—C9—C8 | 121.00 (16) | C24—C25—C26 | 119.62 (18) |
C10—C9—H9 | 119.5 | C24—C25—H25 | 120.2 |
C8—C9—H9 | 119.5 | C26—C25—H25 | 120.2 |
C9—C10—C11 | 120.31 (16) | C27—C26—C25 | 120.19 (18) |
C9—C10—H10 | 119.8 | C27—C26—H26 | 119.9 |
C11—C10—H10 | 119.8 | C25—C26—H26 | 119.9 |
C12—C11—C10 | 119.31 (16) | C26—C27—C22 | 121.04 (16) |
C12—C11—H11 | 120.3 | C26—C27—H27 | 119.5 |
C10—C11—H11 | 120.3 | C22—C27—H27 | 119.5 |
C11—C12—C13 | 120.66 (16) | C14—N1—C5 | 114.06 (11) |
C11—C12—H12 | 119.7 | C14—N1—C1 | 111.87 (11) |
C13—C12—H12 | 119.7 | C5—N1—C1 | 112.30 (11) |
| | | |
N1—C1—C2—C3 | −60.82 (15) | N1—C14—C15—C20 | 100.28 (16) |
C8—C1—C2—C3 | 173.66 (12) | N1—C14—C15—C16 | −81.06 (18) |
N1—C1—C2—C7 | 57.06 (16) | C20—C15—C16—C17 | 1.1 (3) |
C8—C1—C2—C7 | −68.46 (16) | C14—C15—C16—C17 | −177.62 (16) |
C7—C2—C3—O1 | 124.13 (18) | C15—C16—C17—C18 | −1.3 (3) |
C1—C2—C3—O1 | −117.66 (18) | C16—C17—C18—C19 | 0.2 (3) |
C7—C2—C3—C4 | −57.07 (17) | C17—C18—C19—C20 | 1.2 (3) |
C1—C2—C3—C4 | 61.14 (17) | C18—C19—C20—C15 | −1.5 (2) |
O1—C3—C4—C21 | −1.0 (3) | C16—C15—C20—C19 | 0.3 (2) |
C2—C3—C4—C21 | −179.76 (14) | C14—C15—C20—C19 | 178.99 (14) |
O1—C3—C4—C5 | 175.27 (17) | C3—C4—C21—C22 | −178.90 (15) |
C2—C3—C4—C5 | −3.52 (18) | C5—C4—C21—C22 | 5.7 (3) |
C21—C4—C5—N1 | 119.45 (17) | C4—C21—C22—C27 | 38.0 (2) |
C3—C4—C5—N1 | −56.39 (16) | C4—C21—C22—C23 | −141.88 (17) |
C21—C4—C5—C6 | −122.43 (17) | C27—C22—C23—C24 | −3.4 (2) |
C3—C4—C5—C6 | 61.72 (16) | C21—C22—C23—C24 | 176.48 (16) |
N1—C5—C6—C7 | 62.06 (16) | C22—C23—C24—C25 | 2.1 (3) |
C4—C5—C6—C7 | −57.30 (16) | C23—C24—C25—C26 | 0.4 (3) |
C3—C2—C7—C6 | 60.09 (17) | C24—C25—C26—C27 | −1.4 (3) |
C1—C2—C7—C6 | −55.63 (17) | C25—C26—C27—C22 | 0.0 (3) |
C5—C6—C7—C2 | −3.05 (18) | C23—C22—C27—C26 | 2.3 (2) |
N1—C1—C8—C13 | −4.8 (2) | C21—C22—C27—C26 | −177.51 (15) |
C2—C1—C8—C13 | 119.32 (15) | C15—C14—N1—C5 | −73.20 (16) |
N1—C1—C8—C9 | 172.48 (13) | C15—C14—N1—C1 | 157.96 (12) |
C2—C1—C8—C9 | −63.40 (18) | C4—C5—N1—C14 | −71.76 (15) |
C13—C8—C9—C10 | 0.2 (2) | C6—C5—N1—C14 | 168.96 (11) |
C1—C8—C9—C10 | −177.19 (15) | C4—C5—N1—C1 | 56.85 (15) |
C8—C9—C10—C11 | 0.9 (3) | C6—C5—N1—C1 | −62.42 (14) |
C9—C10—C11—C12 | −1.2 (3) | C8—C1—N1—C14 | −101.10 (14) |
C10—C11—C12—C13 | 0.3 (2) | C2—C1—N1—C14 | 132.42 (13) |
C11—C12—C13—C8 | 0.8 (2) | C8—C1—N1—C5 | 129.15 (12) |
C9—C8—C13—C12 | −1.1 (2) | C2—C1—N1—C5 | 2.66 (16) |
C1—C8—C13—C12 | 176.27 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O1i | 0.93 | 2.58 | 3.486 (2) | 166 |
Symmetry code: (i) −x+2, −y, −z+2. |
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