Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028849/cv6565sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028849/cv6565Isup2.hkl |
CCDC reference: 287535
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C)= 0.002 Å
- R factor = 0.049
- wR factor = 0.134
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
To a solution of N-benzylideneaniline (5.5 mmol) in CH2Cl2 (5 ml) at room temperature were sequentially added ZrCl4 (10 mol%) and cyclohexen-2-one (5.5 mmol), and the mixture was stirred for 6 h. After completion of the reaction as indicated by thin-layer chromatography, the reaction was quenched with water, diluted with CH2Cl2 (20 ml) and washed with water (10 ml). The aqueous layer was extracted with CH2Cl2 (2 C 10 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to yield a dark -brown residue, which was purified by column chromatography using 2–10% ethyl acetate in hexane as eluant to obtain the pure product.
H atoms were included in calculated positions and refined as riding, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = 1.2–1.5 Ueq of the parent atom.
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: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C32H28N2 | F(000) = 936 |
Mr = 440.56 | Dx = 1.220 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4667 reflections |
a = 14.6209 (13) Å | θ = 2.4–27.4° |
b = 9.5899 (9) Å | µ = 0.07 mm−1 |
c = 17.9541 (16) Å | T = 273 K |
β = 107.701 (2)° | Needle, colourless |
V = 2398.2 (4) Å3 | 0.19 × 0.11 × 0.09 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4256 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.0°, θmin = 2.4° |
ω scans | h = −18→19 |
14781 measured reflections | k = −7→12 |
5570 independent reflections | l = −23→23 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0634P)2 + 0.3708P] where P = (Fo2 + 2Fc2)/3 |
5570 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C32H28N2 | V = 2398.2 (4) Å3 |
Mr = 440.56 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.6209 (13) Å | µ = 0.07 mm−1 |
b = 9.5899 (9) Å | T = 273 K |
c = 17.9541 (16) Å | 0.19 × 0.11 × 0.09 mm |
β = 107.701 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 4256 reflections with I > 2σ(I) |
14781 measured reflections | Rint = 0.021 |
5570 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.22 e Å−3 |
5570 reflections | Δρmin = −0.20 e Å−3 |
307 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.20593 (7) | 0.03442 (12) | 0.29660 (6) | 0.0376 (3) | |
N3 | 0.45718 (8) | 0.00292 (15) | 0.25162 (7) | 0.0512 (3) | |
C1 | 0.21337 (9) | 0.12376 (14) | 0.23192 (7) | 0.0393 (3) | |
H1 | 0.1516 | 0.1266 | 0.1905 | 0.047* | |
C3 | 0.29596 (9) | 0.02325 (13) | 0.36151 (7) | 0.0338 (3) | |
H3 | 0.2855 | 0.0657 | 0.4079 | 0.041* | |
C4 | 0.37305 (9) | 0.10938 (13) | 0.33955 (7) | 0.0355 (3) | |
H4 | 0.4347 | 0.1027 | 0.3809 | 0.043* | |
C5 | 0.38225 (9) | 0.05212 (13) | 0.26385 (7) | 0.0375 (3) | |
C6 | 0.28961 (9) | 0.06220 (14) | 0.20068 (7) | 0.0376 (3) | |
C7 | 0.24379 (11) | 0.27157 (15) | 0.26173 (8) | 0.0475 (3) | |
H7A | 0.1956 | 0.3130 | 0.2819 | 0.057* | |
H7B | 0.2504 | 0.3295 | 0.2194 | 0.057* | |
C8 | 0.34053 (11) | 0.26202 (14) | 0.32702 (8) | 0.0458 (3) | |
H8A | 0.3885 | 0.3166 | 0.3127 | 0.055* | |
H8B | 0.3338 | 0.2998 | 0.3752 | 0.055* | |
C9 | 0.11982 (9) | 0.03119 (15) | 0.31567 (8) | 0.0419 (3) | |
C10 | 0.03930 (10) | 0.10950 (19) | 0.27615 (9) | 0.0552 (4) | |
H10 | 0.0421 | 0.1695 | 0.2362 | 0.066* | |
C11 | −0.04472 (11) | 0.0985 (2) | 0.29600 (11) | 0.0719 (6) | |
H11 | −0.0979 | 0.1508 | 0.2688 | 0.086* | |
C12 | −0.05102 (13) | 0.0121 (3) | 0.35492 (12) | 0.0787 (6) | |
H12 | −0.1080 | 0.0051 | 0.3675 | 0.094* | |
C13 | 0.02768 (13) | −0.0636 (2) | 0.39490 (11) | 0.0722 (5) | |
H13 | 0.0243 | −0.1215 | 0.4356 | 0.087* | |
C14 | 0.11214 (11) | −0.05574 (18) | 0.37588 (9) | 0.0553 (4) | |
H14 | 0.1646 | −0.1090 | 0.4035 | 0.066* | |
C15 | 0.33078 (9) | −0.12452 (13) | 0.38210 (7) | 0.0362 (3) | |
C16 | 0.39373 (10) | −0.15106 (15) | 0.45586 (8) | 0.0442 (3) | |
H16 | 0.4110 | −0.0793 | 0.4923 | 0.053* | |
C17 | 0.43094 (12) | −0.28273 (17) | 0.47565 (10) | 0.0606 (4) | |
H17 | 0.4728 | −0.2997 | 0.5253 | 0.073* | |
C18 | 0.40612 (14) | −0.38906 (17) | 0.42184 (11) | 0.0695 (5) | |
H18 | 0.4319 | −0.4777 | 0.4349 | 0.083* | |
C19 | 0.34342 (14) | −0.36447 (16) | 0.34890 (10) | 0.0625 (5) | |
H19 | 0.3262 | −0.4368 | 0.3128 | 0.075* | |
C20 | 0.30581 (11) | −0.23289 (15) | 0.32888 (8) | 0.0478 (3) | |
H20 | 0.2634 | −0.2169 | 0.2793 | 0.057* | |
C21 | 0.54531 (10) | −0.00095 (17) | 0.31271 (8) | 0.0476 (3) | |
C22 | 0.57350 (11) | −0.12182 (18) | 0.35546 (9) | 0.0543 (4) | |
H22 | 0.5328 | −0.1986 | 0.3465 | 0.065* | |
C23 | 0.66219 (12) | −0.1283 (2) | 0.41149 (10) | 0.0630 (5) | |
H23 | 0.6801 | −0.2090 | 0.4411 | 0.076* | |
C24 | 0.72403 (12) | −0.0176 (2) | 0.42404 (10) | 0.0667 (5) | |
H24 | 0.7843 | −0.0236 | 0.4611 | 0.080* | |
C25 | 0.69645 (13) | 0.1024 (2) | 0.38157 (11) | 0.0695 (5) | |
H25 | 0.7383 | 0.1779 | 0.3900 | 0.083* | |
C26 | 0.60721 (12) | 0.1121 (2) | 0.32648 (10) | 0.0609 (4) | |
H26 | 0.5886 | 0.1944 | 0.2986 | 0.073* | |
C27 | 0.28157 (10) | 0.02401 (15) | 0.12750 (8) | 0.0440 (3) | |
H27 | 0.3358 | −0.0192 | 0.1214 | 0.053* | |
C28 | 0.20171 (10) | 0.03870 (15) | 0.05507 (8) | 0.0440 (3) | |
C29 | 0.13521 (11) | 0.14620 (16) | 0.04082 (8) | 0.0510 (4) | |
H29 | 0.1374 | 0.2103 | 0.0802 | 0.061* | |
C30 | 0.06598 (13) | 0.15967 (19) | −0.03064 (9) | 0.0619 (4) | |
H30 | 0.0222 | 0.2327 | −0.0389 | 0.074* | |
C31 | 0.06099 (14) | 0.0666 (2) | −0.08957 (10) | 0.0701 (5) | |
H31 | 0.0139 | 0.0759 | −0.1376 | 0.084* | |
C32 | 0.12573 (16) | −0.0398 (2) | −0.07714 (10) | 0.0814 (6) | |
H32 | 0.1226 | −0.1036 | −0.1168 | 0.098* | |
C33 | 0.19572 (14) | −0.0532 (2) | −0.00612 (9) | 0.0695 (5) | |
H33 | 0.2400 | −0.1254 | 0.0011 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0319 (5) | 0.0444 (6) | 0.0351 (5) | 0.0020 (4) | 0.0081 (4) | 0.0040 (4) |
N3 | 0.0391 (6) | 0.0715 (9) | 0.0429 (6) | 0.0072 (6) | 0.0124 (5) | −0.0023 (6) |
C1 | 0.0357 (7) | 0.0446 (7) | 0.0350 (6) | 0.0066 (5) | 0.0071 (5) | 0.0041 (5) |
C3 | 0.0330 (6) | 0.0351 (6) | 0.0327 (6) | 0.0017 (5) | 0.0090 (5) | −0.0004 (5) |
C4 | 0.0331 (6) | 0.0336 (6) | 0.0369 (6) | −0.0005 (5) | 0.0063 (5) | −0.0002 (5) |
C5 | 0.0372 (7) | 0.0373 (7) | 0.0383 (7) | −0.0002 (5) | 0.0118 (5) | 0.0031 (5) |
C6 | 0.0366 (7) | 0.0392 (7) | 0.0361 (6) | 0.0013 (5) | 0.0096 (5) | 0.0034 (5) |
C7 | 0.0536 (8) | 0.0401 (7) | 0.0479 (8) | 0.0115 (6) | 0.0140 (6) | 0.0070 (6) |
C8 | 0.0523 (8) | 0.0326 (7) | 0.0501 (8) | −0.0009 (6) | 0.0121 (6) | −0.0003 (6) |
C9 | 0.0347 (7) | 0.0517 (8) | 0.0387 (7) | −0.0040 (6) | 0.0102 (5) | −0.0097 (6) |
C10 | 0.0386 (8) | 0.0805 (11) | 0.0438 (8) | 0.0066 (7) | 0.0083 (6) | −0.0078 (7) |
C11 | 0.0338 (8) | 0.1176 (16) | 0.0598 (10) | 0.0055 (9) | 0.0078 (7) | −0.0215 (11) |
C12 | 0.0431 (9) | 0.1252 (18) | 0.0745 (12) | −0.0230 (10) | 0.0281 (9) | −0.0323 (12) |
C13 | 0.0601 (11) | 0.0953 (14) | 0.0696 (11) | −0.0240 (10) | 0.0325 (9) | −0.0060 (10) |
C14 | 0.0462 (8) | 0.0661 (10) | 0.0559 (9) | −0.0088 (7) | 0.0192 (7) | 0.0006 (7) |
C15 | 0.0351 (6) | 0.0342 (7) | 0.0393 (7) | 0.0005 (5) | 0.0116 (5) | 0.0020 (5) |
C16 | 0.0462 (8) | 0.0394 (7) | 0.0423 (7) | 0.0031 (6) | 0.0066 (6) | −0.0011 (6) |
C17 | 0.0660 (10) | 0.0466 (9) | 0.0547 (9) | 0.0108 (8) | −0.0033 (7) | 0.0062 (7) |
C18 | 0.0855 (13) | 0.0349 (8) | 0.0755 (11) | 0.0135 (8) | 0.0060 (10) | 0.0047 (8) |
C19 | 0.0826 (12) | 0.0345 (8) | 0.0624 (10) | −0.0016 (7) | 0.0100 (9) | −0.0076 (7) |
C20 | 0.0550 (9) | 0.0385 (7) | 0.0440 (7) | −0.0026 (6) | 0.0063 (6) | −0.0013 (6) |
C21 | 0.0357 (7) | 0.0677 (10) | 0.0420 (7) | 0.0067 (7) | 0.0154 (6) | −0.0056 (7) |
C22 | 0.0474 (8) | 0.0618 (10) | 0.0531 (8) | 0.0079 (7) | 0.0146 (7) | −0.0064 (7) |
C23 | 0.0555 (10) | 0.0795 (12) | 0.0518 (9) | 0.0258 (9) | 0.0128 (7) | −0.0058 (8) |
C24 | 0.0382 (8) | 0.1091 (16) | 0.0495 (9) | 0.0112 (9) | 0.0086 (7) | −0.0188 (10) |
C25 | 0.0469 (9) | 0.0960 (15) | 0.0671 (11) | −0.0145 (9) | 0.0194 (8) | −0.0160 (10) |
C26 | 0.0504 (9) | 0.0744 (11) | 0.0593 (9) | −0.0005 (8) | 0.0191 (7) | 0.0014 (8) |
C27 | 0.0404 (7) | 0.0503 (8) | 0.0414 (7) | 0.0056 (6) | 0.0127 (6) | 0.0000 (6) |
C28 | 0.0462 (8) | 0.0500 (8) | 0.0352 (7) | 0.0008 (6) | 0.0114 (6) | −0.0010 (6) |
C29 | 0.0595 (9) | 0.0500 (8) | 0.0396 (7) | 0.0058 (7) | 0.0095 (6) | −0.0027 (6) |
C30 | 0.0665 (10) | 0.0631 (10) | 0.0482 (9) | 0.0154 (8) | 0.0056 (7) | 0.0028 (8) |
C31 | 0.0784 (12) | 0.0746 (12) | 0.0413 (8) | 0.0070 (10) | −0.0059 (8) | −0.0032 (8) |
C32 | 0.1044 (16) | 0.0809 (14) | 0.0438 (9) | 0.0205 (12) | −0.0001 (9) | −0.0199 (9) |
C33 | 0.0815 (12) | 0.0735 (12) | 0.0472 (9) | 0.0273 (10) | 0.0102 (8) | −0.0094 (8) |
N2—C9 | 1.4020 (17) | C16—C17 | 1.378 (2) |
N2—C3 | 1.4729 (15) | C16—H16 | 0.9300 |
N2—C1 | 1.4735 (17) | C17—C18 | 1.375 (2) |
N3—C5 | 1.2717 (17) | C17—H17 | 0.9300 |
N3—C21 | 1.4160 (18) | C18—C19 | 1.372 (2) |
C1—C6 | 1.5119 (18) | C18—H18 | 0.9300 |
C1—C7 | 1.533 (2) | C19—C20 | 1.380 (2) |
C1—H1 | 0.9800 | C19—H19 | 0.9300 |
C3—C15 | 1.5131 (17) | C20—H20 | 0.9300 |
C3—C4 | 1.5422 (17) | C21—C22 | 1.382 (2) |
C3—H3 | 0.9800 | C21—C26 | 1.385 (2) |
C4—C5 | 1.5093 (18) | C22—C23 | 1.380 (2) |
C4—C8 | 1.5344 (18) | C22—H22 | 0.9300 |
C4—H4 | 0.9800 | C23—C24 | 1.369 (3) |
C5—C6 | 1.4819 (17) | C23—H23 | 0.9300 |
C6—C27 | 1.3343 (18) | C24—C25 | 1.372 (3) |
C7—C8 | 1.541 (2) | C24—H24 | 0.9300 |
C7—H7A | 0.9700 | C25—C26 | 1.380 (2) |
C7—H7B | 0.9700 | C25—H25 | 0.9300 |
C8—H8A | 0.9700 | C26—H26 | 0.9300 |
C8—H8B | 0.9700 | C27—C28 | 1.4666 (18) |
C9—C10 | 1.395 (2) | C27—H27 | 0.9300 |
C9—C14 | 1.396 (2) | C28—C29 | 1.386 (2) |
C10—C11 | 1.383 (2) | C28—C33 | 1.390 (2) |
C10—H10 | 0.9300 | C29—C30 | 1.378 (2) |
C11—C12 | 1.369 (3) | C29—H29 | 0.9300 |
C11—H11 | 0.9300 | C30—C31 | 1.369 (2) |
C12—C13 | 1.366 (3) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—C32 | 1.363 (3) |
C13—C14 | 1.380 (2) | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | C32—C33 | 1.377 (2) |
C14—H14 | 0.9300 | C32—H32 | 0.9300 |
C15—C20 | 1.3836 (18) | C33—H33 | 0.9300 |
C15—C16 | 1.3872 (18) | ||
C9—N2—C3 | 117.26 (10) | C20—C15—C16 | 118.72 (12) |
C9—N2—C1 | 119.49 (10) | C20—C15—C3 | 122.43 (11) |
C3—N2—C1 | 113.80 (10) | C16—C15—C3 | 118.78 (11) |
C5—N3—C21 | 120.31 (12) | C17—C16—C15 | 120.64 (13) |
N2—C1—C6 | 107.74 (10) | C17—C16—H16 | 119.7 |
N2—C1—C7 | 110.22 (10) | C15—C16—H16 | 119.7 |
C6—C1—C7 | 108.80 (11) | C18—C17—C16 | 119.94 (14) |
N2—C1—H1 | 110.0 | C18—C17—H17 | 120.0 |
C6—C1—H1 | 110.0 | C16—C17—H17 | 120.0 |
C7—C1—H1 | 110.0 | C19—C18—C17 | 120.01 (14) |
N2—C3—C15 | 114.51 (10) | C19—C18—H18 | 120.0 |
N2—C3—C4 | 107.79 (10) | C17—C18—H18 | 120.0 |
C15—C3—C4 | 110.26 (10) | C18—C19—C20 | 120.25 (15) |
N2—C3—H3 | 108.0 | C18—C19—H19 | 119.9 |
C15—C3—H3 | 108.0 | C20—C19—H19 | 119.9 |
C4—C3—H3 | 108.0 | C19—C20—C15 | 120.44 (13) |
C5—C4—C8 | 108.88 (11) | C19—C20—H20 | 119.8 |
C5—C4—C3 | 107.91 (10) | C15—C20—H20 | 119.8 |
C8—C4—C3 | 109.30 (10) | C22—C21—C26 | 119.26 (14) |
C5—C4—H4 | 110.2 | C22—C21—N3 | 119.98 (14) |
C8—C4—H4 | 110.2 | C26—C21—N3 | 120.59 (15) |
C3—C4—H4 | 110.2 | C23—C22—C21 | 119.89 (16) |
N3—C5—C6 | 121.80 (12) | C23—C22—H22 | 120.1 |
N3—C5—C4 | 127.43 (12) | C21—C22—H22 | 120.1 |
C6—C5—C4 | 110.76 (11) | C24—C23—C22 | 120.82 (17) |
C27—C6—C5 | 121.47 (12) | C24—C23—H23 | 119.6 |
C27—C6—C1 | 128.19 (12) | C22—C23—H23 | 119.6 |
C5—C6—C1 | 110.31 (11) | C23—C24—C25 | 119.46 (15) |
C1—C7—C8 | 108.21 (10) | C23—C24—H24 | 120.3 |
C1—C7—H7A | 110.1 | C25—C24—H24 | 120.3 |
C8—C7—H7A | 110.1 | C24—C25—C26 | 120.59 (18) |
C1—C7—H7B | 110.1 | C24—C25—H25 | 119.7 |
C8—C7—H7B | 110.1 | C26—C25—H25 | 119.7 |
H7A—C7—H7B | 108.4 | C25—C26—C21 | 119.97 (18) |
C4—C8—C7 | 109.88 (11) | C25—C26—H26 | 120.0 |
C4—C8—H8A | 109.7 | C21—C26—H26 | 120.0 |
C7—C8—H8A | 109.7 | C6—C27—C28 | 130.91 (13) |
C4—C8—H8B | 109.7 | C6—C27—H27 | 114.5 |
C7—C8—H8B | 109.7 | C28—C27—H27 | 114.5 |
H8A—C8—H8B | 108.2 | C29—C28—C33 | 116.96 (13) |
C10—C9—C14 | 117.47 (13) | C29—C28—C27 | 124.03 (13) |
C10—C9—N2 | 123.06 (13) | C33—C28—C27 | 118.80 (13) |
C14—C9—N2 | 119.46 (13) | C30—C29—C28 | 121.14 (14) |
C11—C10—C9 | 120.40 (17) | C30—C29—H29 | 119.4 |
C11—C10—H10 | 119.8 | C28—C29—H29 | 119.4 |
C9—C10—H10 | 119.8 | C31—C30—C29 | 120.67 (16) |
C12—C11—C10 | 121.28 (17) | C31—C30—H30 | 119.7 |
C12—C11—H11 | 119.4 | C29—C30—H30 | 119.7 |
C10—C11—H11 | 119.4 | C32—C31—C30 | 119.35 (15) |
C13—C12—C11 | 118.96 (16) | C32—C31—H31 | 120.3 |
C13—C12—H12 | 120.5 | C30—C31—H31 | 120.3 |
C11—C12—H12 | 120.5 | C31—C32—C33 | 120.33 (16) |
C12—C13—C14 | 121.02 (19) | C31—C32—H32 | 119.8 |
C12—C13—H13 | 119.5 | C33—C32—H32 | 119.8 |
C14—C13—H13 | 119.5 | C32—C33—C28 | 121.55 (16) |
C13—C14—C9 | 120.87 (17) | C32—C33—H33 | 119.2 |
C13—C14—H14 | 119.6 | C28—C33—H33 | 119.2 |
C9—C14—H14 | 119.6 | ||
C9—N2—C1—C6 | −154.80 (11) | C11—C12—C13—C14 | −1.0 (3) |
C3—N2—C1—C6 | 59.66 (13) | C12—C13—C14—C9 | 0.7 (3) |
C9—N2—C1—C7 | 86.62 (14) | C10—C9—C14—C13 | 0.3 (2) |
C3—N2—C1—C7 | −58.93 (13) | N2—C9—C14—C13 | −178.53 (15) |
C9—N2—C3—C15 | 89.29 (14) | N2—C3—C15—C20 | 24.50 (18) |
C1—N2—C3—C15 | −124.35 (11) | C4—C3—C15—C20 | −97.26 (14) |
C9—N2—C3—C4 | −147.61 (11) | N2—C3—C15—C16 | −158.66 (12) |
C1—N2—C3—C4 | −1.25 (14) | C4—C3—C15—C16 | 79.58 (15) |
N2—C3—C4—C5 | −58.23 (12) | C20—C15—C16—C17 | 0.2 (2) |
C15—C3—C4—C5 | 67.43 (12) | C3—C15—C16—C17 | −176.72 (14) |
N2—C3—C4—C8 | 60.03 (13) | C15—C16—C17—C18 | 0.4 (3) |
C15—C3—C4—C8 | −174.31 (10) | C16—C17—C18—C19 | −0.8 (3) |
C21—N3—C5—C6 | 177.92 (13) | C17—C18—C19—C20 | 0.7 (3) |
C21—N3—C5—C4 | −0.8 (2) | C18—C19—C20—C15 | −0.1 (3) |
C8—C4—C5—N3 | 120.09 (15) | C16—C15—C20—C19 | −0.4 (2) |
C3—C4—C5—N3 | −121.38 (15) | C3—C15—C20—C19 | 176.46 (14) |
C8—C4—C5—C6 | −58.72 (14) | C5—N3—C21—C22 | 96.93 (18) |
C3—C4—C5—C6 | 59.81 (13) | C5—N3—C21—C26 | −87.88 (18) |
N3—C5—C6—C27 | −2.1 (2) | C26—C21—C22—C23 | 0.5 (2) |
C4—C5—C6—C27 | 176.75 (13) | N3—C21—C22—C23 | 175.75 (13) |
N3—C5—C6—C1 | 179.76 (13) | C21—C22—C23—C24 | −1.7 (2) |
C4—C5—C6—C1 | −1.35 (15) | C22—C23—C24—C25 | 1.5 (3) |
N2—C1—C6—C27 | 124.37 (15) | C23—C24—C25—C26 | −0.1 (3) |
C7—C1—C6—C27 | −116.14 (15) | C24—C25—C26—C21 | −1.2 (3) |
N2—C1—C6—C5 | −57.69 (13) | C22—C21—C26—C25 | 0.9 (2) |
C7—C1—C6—C5 | 61.80 (13) | N3—C21—C26—C25 | −174.28 (14) |
N2—C1—C7—C8 | 58.07 (14) | C5—C6—C27—C28 | −172.43 (14) |
C6—C1—C7—C8 | −59.86 (14) | C1—C6—C27—C28 | 5.3 (3) |
C5—C4—C8—C7 | 58.81 (14) | C6—C27—C28—C29 | 30.1 (3) |
C3—C4—C8—C7 | −58.84 (14) | C6—C27—C28—C33 | −155.41 (17) |
C1—C7—C8—C4 | 0.14 (16) | C33—C28—C29—C30 | 0.7 (2) |
C3—N2—C9—C10 | 144.28 (13) | C27—C28—C29—C30 | 175.24 (15) |
C1—N2—C9—C10 | −0.10 (19) | C28—C29—C30—C31 | 0.1 (3) |
C3—N2—C9—C14 | −36.97 (18) | C29—C30—C31—C32 | −0.3 (3) |
C1—N2—C9—C14 | 178.64 (12) | C30—C31—C32—C33 | −0.3 (3) |
C14—C9—C10—C11 | −0.9 (2) | C31—C32—C33—C28 | 1.1 (3) |
N2—C9—C10—C11 | 177.88 (14) | C29—C28—C33—C32 | −1.3 (3) |
C9—C10—C11—C12 | 0.6 (3) | C27—C28—C33—C32 | −176.17 (18) |
C10—C11—C12—C13 | 0.4 (3) |
Experimental details
Crystal data | |
Chemical formula | C32H28N2 |
Mr | 440.56 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 14.6209 (13), 9.5899 (9), 17.9541 (16) |
β (°) | 107.701 (2) |
V (Å3) | 2398.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.19 × 0.11 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14781, 5570, 4256 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.134, 1.05 |
No. of reflections | 5570 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97.
N2—C1 | 1.4735 (17) | C5—C6 | 1.4819 (17) |
N3—C5 | 1.2717 (17) | C6—C27 | 1.3343 (18) |
C1—C6 | 1.5119 (18) | ||
N3—C5—C6 | 121.80 (12) | C26—C21—N3 | 120.59 (15) |
C27—C6—C5 | 121.47 (12) | C29—C28—C33 | 116.96 (13) |
C22—C21—N3 | 119.98 (14) | C29—C28—C27 | 124.03 (13) |
C1—N2—C9—C10 | −0.10 (19) | C5—N3—C21—C22 | 96.93 (18) |
C4—C3—C15—C16 | 79.58 (15) | C6—C27—C28—C29 | 30.1 (3) |
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The presence of an isoquinuclidine ring system in a molecule is frequently associated with significant pharmacological properties (Iriepa et al., 2002). In addition, it also acts as a precursor for the synthesis of naturally occurring piperidine alkaloids of the prosopis family (Birkinshaw et al., 1988). The structure of the title compound, (I), is reported here as a part of our ongoing structural study of this series of compounds (Ravikumar et al., 2005).
The molecule of (I) consists of four planar benzene rings, two of which are directly connected to the azabicyclic system while the other two are connected through a double-bond linkage as an extended `arm' (Fig. 1). All the bond lengths and angles (Table 1) are in a good agreement with those found in related structures (Sonar et al., 2003, 2004).
The geometrical isomerism around the double bonds C6═C27 and C5═N3 affords the possibility of E and Z isomers. The C27—C28 bond is in a trans configuration with respect to the C5—C6 bond [C5—C6—C27—C28 = −172.43 (14)°]. Similarly, the N3—C21 bond is also in a trans disposition with respect to the C5—C6 bond [C6—C5—N3—C21 = 177.92 (13) Å]. The bond angles around atoms C6, C21 and C28 are close to the ideal value of 120°, while the C1—C6—C27 [128.2 (1)°] and N3—C5—C4 [127.4 (1)°] angles are more distorted, as a consequence of the strain induced by the C6═C27 and C5═N3 double-bond linkages. Atom N2 is in pyramidal configuration and the sum of the angles around the atom is 350.6 (1)°.
All three six-membered rings of the azabicyclo[2.2.2] system adopt the expected boat conformation, with asymmetry parameters (Nardelli, 1983) ΔCs(C1) of 0.015 (1), 0.289 (1) and 0.002 (1) for the rings C3/N2/C1/C7/C8/C4, C1/C4–C8 and C1/N2/C3–C6, respectively. In the absence of H-atom-donating groups, the crystal packing (Fig. 2) is stabilized by van der Waals forces.