Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051781/sj2382sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051781/sj2382Isup2.hkl |
CCDC reference: 667438
An aqueous solution of sodium hydroxide (10% w/v, 30 ml) was added to a solution of 3,4-dimethoxybenzaldehyde (3.32 g, 0.02 mol) and γ-ethylcyclohexanone (1.4 ml, 0.01 mol) in ethanol (50 ml). The reaction mixture was stirred at 10–20 ° for 2 hr and left overnight in an ice chest forming a yellow colored solid. The product was filtered, washed with ice-cold water (100 ml) followed by ice-cold ethanol (20 ml), dried and recrystallized from alcohol. The yield of product, m.p.138–139 °, was 81%.
All the H atoms were located in a difference Fourier map and refined isotropically with C—H bond lengths in the range 0.89 (4)–0.94 (3) Å.
Substituted 2,6-bis(benzylidenecyclohexanone) derivatives have been the subject of recent crystallographic investigations and have found useful applications as potent anti-cancer agents (Dimmock et al., 2001, 2005).
The six-membered cyclohexanone ring exists in an envelope conformation, the Cremer and Pople puckering parameters are Q(T) = 0.546 (2) Å, φ(2) = 172.5 (3)°, θ (2) = 57.3 (2)° (Cremer and Pople, 1975). The ring atom C24 deviates by +0.406 (6) Å from the least squares plane passing through C2/C4/C7/C8/C17. The C24 ring atom deviates by +0.406 (6) Å from the least squares plane passing through C2/C4/C7/C8/C17. Also the C6—C7—C8, 129.8 (2) and C2—C16—C17 130.2 (2) ° angles and the torsion angles about the C7—C8 24.4 (4) ° and C16—C17 - 31.9 (4)° bonds also deviate from planarity indicating significant steric repulsion between the aryl ring and the cyclohexanone ring, with repulsions in particular between the hydrogen atoms H18···H3B, 2.284 Å and H9···H5A 2.209 Å respectively. The crystal packing is stabilized by C—H···O intermolecular interactions forming C(7) molecular chains (Bernstein et al., 1995) along the crystallographic b axis.
For related structures, see: Dimmock et al. (2001, 2005)
For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. Molecular structure of (I), showing 50% ellipsoidal probability. | |
Fig. 2. Packing diagram of (I). The dotted lines show C—H···O hydrogen bonds. |
C26H30O5 | F(000) = 904 |
Mr = 422.5 | Dx = 1.269 Mg m−3 |
Monoclinic, P21/n | Melting point: 670.44 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3766 (10) Å | Cell parameters from 2836 reflections |
b = 8.6973 (9) Å | θ = 2.5–23.5° |
c = 24.555 (3) Å | µ = 0.09 mm−1 |
β = 93.500 (2)° | T = 273 K |
V = 2212.0 (4) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.21 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 5285 independent reflections |
Radiation source: fine-focus sealed tube | 3034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −13→11 |
Tmin = 0.983, Tmax = 0.986 | k = −11→11 |
18534 measured reflections | l = −31→32 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0842P)2 + 0.3153P] where P = (Fo2 + 2Fc2)/3 |
5285 reflections | (Δ/σ)max = 0.001 |
285 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C26H30O5 | V = 2212.0 (4) Å3 |
Mr = 422.5 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.3766 (10) Å | µ = 0.09 mm−1 |
b = 8.6973 (9) Å | T = 273 K |
c = 24.555 (3) Å | 0.25 × 0.21 × 0.20 mm |
β = 93.500 (2)° |
Bruker SMART CCD area-detector diffractometer | 5285 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 3034 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.986 | Rint = 0.055 |
18534 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.34 e Å−3 |
5285 reflections | Δρmin = −0.19 e Å−3 |
285 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 | ||
O3 | 0.25921 (17) | −0.51272 (18) | 1.18110 (6) | 0.0502 (5) | |
O4 | 0.08370 (19) | 0.64202 (18) | 0.69106 (7) | 0.0559 (5) | |
O2 | 0.25180 (18) | −0.21513 (17) | 1.17688 (6) | 0.0508 (5) | |
C10 | 0.2184 (2) | −0.2892 (2) | 1.12918 (8) | 0.0371 (5) | |
C11 | 0.2215 (2) | −0.4510 (2) | 1.13192 (8) | 0.0373 (5) | |
O1 | 0.0307 (2) | −0.1498 (2) | 0.87689 (8) | 0.0793 (7) | |
O5 | 0.0943 (2) | 0.36852 (19) | 0.64952 (7) | 0.0633 (6) | |
C8 | 0.1502 (2) | −0.3001 (3) | 1.03314 (9) | 0.0384 (6) | |
C21 | 0.0922 (3) | 0.3754 (3) | 0.70512 (9) | 0.0445 (6) | |
C2 | 0.1249 (2) | 0.0979 (3) | 0.88009 (9) | 0.0392 (6) | |
C9 | 0.1824 (2) | −0.2170 (3) | 1.08089 (9) | 0.0388 (6) | |
H9 | 0.1793 | −0.1102 | 1.0799 | 0.047* | |
C6 | 0.1473 (2) | −0.0922 (3) | 0.96042 (9) | 0.0405 (6) | |
C16 | 0.0823 (2) | 0.1245 (3) | 0.82837 (9) | 0.0435 (6) | |
H16 | 0.0433 | 0.0407 | 0.8105 | 0.052* | |
C7 | 0.1164 (2) | −0.2306 (3) | 0.97992 (9) | 0.0425 (6) | |
H7 | 0.0658 | −0.2916 | 0.9560 | 0.051* | |
C17 | 0.0875 (2) | 0.2643 (3) | 0.79554 (9) | 0.0410 (6) | |
C15 | 0.2665 (3) | −0.0521 (3) | 1.17406 (10) | 0.0536 (7) | |
H15A | 0.3298 | −0.0273 | 1.1485 | 0.080* | |
H15B | 0.2942 | −0.0131 | 1.2094 | 0.080* | |
H15C | 0.1854 | −0.0061 | 1.1623 | 0.080* | |
C22 | 0.0908 (2) | 0.2500 (3) | 0.73870 (9) | 0.0450 (6) | |
H22 | 0.0921 | 0.1522 | 0.7234 | 0.054* | |
C12 | 0.1847 (3) | −0.5342 (3) | 1.08564 (9) | 0.0454 (6) | |
H12 | 0.1831 | −0.6411 | 1.0871 | 0.054* | |
C3 | 0.2037 (2) | 0.2092 (3) | 0.91474 (9) | 0.0446 (6) | |
H3A | 0.1474 | 0.2671 | 0.9373 | 0.053* | |
H3B | 0.2458 | 0.2813 | 0.8914 | 0.053* | |
C20 | 0.0866 (2) | 0.5240 (3) | 0.72757 (9) | 0.0428 (6) | |
C13 | 0.1501 (2) | −0.4595 (3) | 1.03715 (9) | 0.0451 (6) | |
H13 | 0.1261 | −0.5176 | 1.0064 | 0.054* | |
C4 | 0.3058 (2) | 0.1258 (3) | 0.95126 (9) | 0.0439 (6) | |
H4 | 0.3560 | 0.0601 | 0.9280 | 0.053* | |
C1 | 0.0966 (3) | −0.0552 (3) | 0.90345 (9) | 0.0467 (6) | |
C18 | 0.0819 (2) | 0.4114 (3) | 0.81681 (9) | 0.0468 (6) | |
H18 | 0.0779 | 0.4244 | 0.8543 | 0.056* | |
C19 | 0.0819 (2) | 0.5396 (3) | 0.78330 (10) | 0.0458 (6) | |
H19 | 0.0788 | 0.6373 | 0.7986 | 0.055* | |
C25 | 0.3987 (3) | 0.2322 (3) | 0.98288 (10) | 0.0538 (7) | |
H25A | 0.3496 | 0.3000 | 1.0052 | 0.065* | |
H25B | 0.4549 | 0.1709 | 1.0073 | 0.065* | |
C5 | 0.2348 (2) | 0.0220 (3) | 0.98994 (9) | 0.0469 (6) | |
H5A | 0.2978 | −0.0330 | 1.0133 | 0.056* | |
H5B | 0.1840 | 0.0856 | 1.0130 | 0.056* | |
C23 | 0.1095 (3) | 0.2212 (3) | 0.62546 (10) | 0.0645 (8) | |
H23A | 0.1869 | 0.1738 | 0.6409 | 0.097* | |
H23B | 0.1153 | 0.2325 | 0.5868 | 0.097* | |
H23C | 0.0365 | 0.1579 | 0.6324 | 0.097* | |
C14 | 0.2557 (3) | −0.6761 (3) | 1.18519 (10) | 0.0549 (7) | |
H14A | 0.1693 | −0.7117 | 1.1766 | 0.082* | |
H14B | 0.2829 | −0.7065 | 1.2217 | 0.082* | |
H14C | 0.3126 | −0.7201 | 1.1600 | 0.082* | |
C24 | 0.0659 (3) | 0.7937 (3) | 0.71203 (12) | 0.0623 (8) | |
H24A | −0.0154 | 0.7991 | 0.7286 | 0.093* | |
H24B | 0.0667 | 0.8668 | 0.6827 | 0.093* | |
H24C | 0.1345 | 0.8170 | 0.7388 | 0.093* | |
C26 | 0.4803 (3) | 0.3281 (4) | 0.94805 (13) | 0.0776 (10) | |
H26A | 0.5198 | 0.2635 | 0.9221 | 0.116* | |
H26B | 0.5462 | 0.3786 | 0.9706 | 0.116* | |
H26C | 0.4274 | 0.4038 | 0.9290 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0763 (13) | 0.0321 (9) | 0.0405 (9) | −0.0047 (8) | −0.0098 (8) | 0.0072 (7) |
O4 | 0.0767 (14) | 0.0348 (10) | 0.0564 (11) | 0.0028 (9) | 0.0048 (9) | 0.0091 (8) |
O2 | 0.0826 (14) | 0.0329 (9) | 0.0354 (8) | −0.0086 (9) | −0.0088 (8) | −0.0009 (7) |
C10 | 0.0446 (15) | 0.0325 (12) | 0.0340 (11) | −0.0060 (11) | 0.0015 (10) | −0.0025 (9) |
C11 | 0.0442 (15) | 0.0307 (12) | 0.0370 (11) | −0.0031 (11) | 0.0022 (10) | 0.0050 (9) |
O1 | 0.1210 (19) | 0.0558 (12) | 0.0556 (11) | −0.0415 (12) | −0.0395 (12) | 0.0182 (9) |
O5 | 0.1096 (17) | 0.0416 (10) | 0.0383 (9) | 0.0034 (10) | 0.0019 (10) | 0.0059 (8) |
C8 | 0.0440 (15) | 0.0341 (13) | 0.0367 (11) | −0.0055 (11) | −0.0010 (10) | 0.0011 (9) |
C21 | 0.0544 (16) | 0.0406 (14) | 0.0381 (12) | 0.0009 (12) | −0.0001 (11) | 0.0034 (10) |
C2 | 0.0421 (15) | 0.0370 (13) | 0.0379 (12) | −0.0053 (11) | −0.0024 (10) | 0.0036 (10) |
C9 | 0.0467 (15) | 0.0297 (12) | 0.0399 (12) | −0.0039 (11) | 0.0016 (10) | 0.0019 (9) |
C6 | 0.0458 (15) | 0.0403 (13) | 0.0347 (11) | −0.0070 (11) | −0.0035 (10) | 0.0044 (10) |
C16 | 0.0499 (16) | 0.0379 (13) | 0.0422 (12) | −0.0054 (12) | −0.0020 (11) | 0.0003 (10) |
C7 | 0.0522 (16) | 0.0406 (14) | 0.0337 (11) | −0.0078 (12) | −0.0050 (10) | 0.0017 (10) |
C17 | 0.0415 (15) | 0.0405 (13) | 0.0402 (12) | −0.0008 (11) | −0.0037 (10) | 0.0040 (10) |
C15 | 0.078 (2) | 0.0309 (13) | 0.0502 (14) | −0.0101 (13) | −0.0094 (13) | −0.0047 (11) |
C22 | 0.0561 (17) | 0.0352 (13) | 0.0427 (13) | −0.0005 (12) | −0.0051 (11) | 0.0019 (10) |
C12 | 0.0659 (18) | 0.0269 (12) | 0.0429 (13) | −0.0043 (12) | 0.0008 (12) | 0.0004 (10) |
C3 | 0.0537 (17) | 0.0400 (14) | 0.0392 (12) | −0.0122 (12) | −0.0044 (11) | 0.0056 (10) |
C20 | 0.0465 (16) | 0.0339 (13) | 0.0474 (13) | −0.0002 (11) | −0.0026 (11) | 0.0078 (10) |
C13 | 0.0622 (18) | 0.0353 (13) | 0.0370 (12) | −0.0063 (12) | −0.0046 (11) | −0.0066 (10) |
C4 | 0.0526 (16) | 0.0398 (13) | 0.0385 (12) | −0.0080 (12) | −0.0035 (11) | −0.0001 (10) |
C1 | 0.0550 (17) | 0.0428 (14) | 0.0408 (13) | −0.0099 (12) | −0.0100 (11) | 0.0046 (11) |
C18 | 0.0528 (17) | 0.0500 (15) | 0.0370 (12) | 0.0004 (13) | −0.0019 (11) | 0.0000 (11) |
C19 | 0.0480 (16) | 0.0385 (14) | 0.0505 (14) | 0.0006 (12) | −0.0007 (11) | −0.0041 (11) |
C25 | 0.0548 (18) | 0.0519 (16) | 0.0538 (15) | −0.0122 (13) | −0.0032 (13) | −0.0014 (12) |
C5 | 0.0546 (17) | 0.0461 (14) | 0.0384 (12) | −0.0137 (12) | −0.0099 (11) | 0.0069 (11) |
C23 | 0.098 (3) | 0.0528 (17) | 0.0424 (14) | 0.0097 (16) | 0.0054 (15) | −0.0049 (12) |
C14 | 0.081 (2) | 0.0314 (13) | 0.0509 (15) | 0.0020 (13) | −0.0035 (14) | 0.0093 (11) |
C24 | 0.079 (2) | 0.0330 (14) | 0.0750 (19) | 0.0041 (14) | 0.0029 (16) | 0.0057 (13) |
C26 | 0.069 (2) | 0.087 (2) | 0.077 (2) | −0.0365 (19) | 0.0017 (17) | −0.0004 (18) |
O3—C11 | 1.357 (2) | C22—H22 | 0.9300 |
O3—C14 | 1.425 (3) | C12—C13 | 1.384 (3) |
O4—C20 | 1.362 (3) | C12—H12 | 0.9300 |
O4—C24 | 1.432 (3) | C3—C4 | 1.528 (3) |
O2—C10 | 1.363 (2) | C3—H3A | 0.9700 |
O2—C15 | 1.429 (3) | C3—H3B | 0.9700 |
C10—C9 | 1.373 (3) | C20—C19 | 1.379 (3) |
C10—C11 | 1.409 (3) | C13—H13 | 0.9300 |
C11—C12 | 1.382 (3) | C4—C25 | 1.516 (3) |
O1—C1 | 1.231 (3) | C4—C5 | 1.532 (3) |
O5—C21 | 1.368 (3) | C4—H4 | 0.9800 |
O5—C23 | 1.424 (3) | C18—C19 | 1.386 (3) |
C8—C13 | 1.390 (3) | C18—H18 | 0.9300 |
C8—C9 | 1.400 (3) | C19—H19 | 0.9300 |
C8—C7 | 1.463 (3) | C25—C26 | 1.494 (4) |
C21—C22 | 1.368 (3) | C25—H25A | 0.9700 |
C21—C20 | 1.407 (3) | C25—H25B | 0.9700 |
C2—C16 | 1.339 (3) | C5—H5A | 0.9700 |
C2—C1 | 1.486 (3) | C5—H5B | 0.9700 |
C2—C3 | 1.499 (3) | C23—H23A | 0.9600 |
C9—H9 | 0.9300 | C23—H23B | 0.9600 |
C6—C7 | 1.341 (3) | C23—H23C | 0.9600 |
C6—C1 | 1.499 (3) | C14—H14A | 0.9600 |
C6—C5 | 1.502 (3) | C14—H14B | 0.9600 |
C16—C17 | 1.462 (3) | C14—H14C | 0.9600 |
C16—H16 | 0.9300 | C24—H24A | 0.9600 |
C7—H7 | 0.9300 | C24—H24B | 0.9600 |
C17—C18 | 1.384 (3) | C24—H24C | 0.9600 |
C17—C22 | 1.404 (3) | C26—H26A | 0.9600 |
C15—H15A | 0.9600 | C26—H26B | 0.9600 |
C15—H15B | 0.9600 | C26—H26C | 0.9600 |
C15—H15C | 0.9600 | ||
C11—O3—C14 | 116.73 (18) | C12—C13—C8 | 121.9 (2) |
C20—O4—C24 | 117.13 (19) | C12—C13—H13 | 119.1 |
C10—O2—C15 | 116.75 (17) | C8—C13—H13 | 119.1 |
O2—C10—C9 | 124.6 (2) | C25—C4—C3 | 114.0 (2) |
O2—C10—C11 | 115.29 (19) | C25—C4—C5 | 110.94 (19) |
C9—C10—C11 | 120.1 (2) | C3—C4—C5 | 107.5 (2) |
O3—C11—C12 | 125.1 (2) | C25—C4—H4 | 108.1 |
O3—C11—C10 | 116.22 (19) | C3—C4—H4 | 108.1 |
C12—C11—C10 | 118.7 (2) | C5—C4—H4 | 108.1 |
C21—O5—C23 | 117.55 (18) | O1—C1—C2 | 120.7 (2) |
C13—C8—C9 | 117.2 (2) | O1—C1—C6 | 120.2 (2) |
C13—C8—C7 | 118.3 (2) | C2—C1—C6 | 119.1 (2) |
C9—C8—C7 | 124.5 (2) | C17—C18—C19 | 121.2 (2) |
O5—C21—C22 | 124.6 (2) | C17—C18—H18 | 119.4 |
O5—C21—C20 | 115.8 (2) | C19—C18—H18 | 119.4 |
C22—C21—C20 | 119.6 (2) | C20—C19—C18 | 120.7 (2) |
C16—C2—C1 | 117.3 (2) | C20—C19—H19 | 119.6 |
C16—C2—C3 | 124.3 (2) | C18—C19—H19 | 119.6 |
C1—C2—C3 | 118.26 (19) | C26—C25—C4 | 114.4 (2) |
C10—C9—C8 | 121.7 (2) | C26—C25—H25A | 108.7 |
C10—C9—H9 | 119.1 | C4—C25—H25A | 108.7 |
C8—C9—H9 | 119.1 | C26—C25—H25B | 108.7 |
C7—C6—C1 | 116.6 (2) | C4—C25—H25B | 108.7 |
C7—C6—C5 | 124.9 (2) | H25A—C25—H25B | 107.6 |
C1—C6—C5 | 118.41 (19) | C6—C5—C4 | 112.95 (18) |
C2—C16—C17 | 130.2 (2) | C6—C5—H5A | 109.0 |
C2—C16—H16 | 114.9 | C4—C5—H5A | 109.0 |
C17—C16—H16 | 114.9 | C6—C5—H5B | 109.0 |
C6—C7—C8 | 129.8 (2) | C4—C5—H5B | 109.0 |
C6—C7—H7 | 115.1 | H5A—C5—H5B | 107.8 |
C8—C7—H7 | 115.1 | O5—C23—H23A | 109.5 |
C18—C17—C22 | 117.5 (2) | O5—C23—H23B | 109.5 |
C18—C17—C16 | 123.8 (2) | H23A—C23—H23B | 109.5 |
C22—C17—C16 | 118.6 (2) | O5—C23—H23C | 109.5 |
O2—C15—H15A | 109.5 | H23A—C23—H23C | 109.5 |
O2—C15—H15B | 109.5 | H23B—C23—H23C | 109.5 |
H15A—C15—H15B | 109.5 | O3—C14—H14A | 109.5 |
O2—C15—H15C | 109.5 | O3—C14—H14B | 109.5 |
H15A—C15—H15C | 109.5 | H14A—C14—H14B | 109.5 |
H15B—C15—H15C | 109.5 | O3—C14—H14C | 109.5 |
C21—C22—C17 | 122.0 (2) | H14A—C14—H14C | 109.5 |
C21—C22—H22 | 119.0 | H14B—C14—H14C | 109.5 |
C17—C22—H22 | 119.0 | O4—C24—H24A | 109.5 |
C11—C12—C13 | 120.4 (2) | O4—C24—H24B | 109.5 |
C11—C12—H12 | 119.8 | H24A—C24—H24B | 109.5 |
C13—C12—H12 | 119.8 | O4—C24—H24C | 109.5 |
C2—C3—C4 | 111.17 (19) | H24A—C24—H24C | 109.5 |
C2—C3—H3A | 109.4 | H24B—C24—H24C | 109.5 |
C4—C3—H3A | 109.4 | C25—C26—H26A | 109.5 |
C2—C3—H3B | 109.4 | C25—C26—H26B | 109.5 |
C4—C3—H3B | 109.4 | H26A—C26—H26B | 109.5 |
H3A—C3—H3B | 108.0 | C25—C26—H26C | 109.5 |
O4—C20—C19 | 125.3 (2) | H26A—C26—H26C | 109.5 |
O4—C20—C21 | 115.7 (2) | H26B—C26—H26C | 109.5 |
C19—C20—C21 | 119.0 (2) | ||
C15—O2—C10—C9 | −8.7 (3) | C24—O4—C20—C19 | −4.3 (4) |
C15—O2—C10—C11 | 171.9 (2) | C24—O4—C20—C21 | 174.4 (2) |
C14—O3—C11—C12 | −2.3 (3) | O5—C21—C20—O4 | 0.1 (3) |
C14—O3—C11—C10 | 176.6 (2) | C22—C21—C20—O4 | −177.7 (2) |
O2—C10—C11—O3 | −1.1 (3) | O5—C21—C20—C19 | 178.9 (2) |
C9—C10—C11—O3 | 179.5 (2) | C22—C21—C20—C19 | 1.0 (4) |
O2—C10—C11—C12 | 177.8 (2) | C11—C12—C13—C8 | −0.4 (4) |
C9—C10—C11—C12 | −1.6 (4) | C9—C8—C13—C12 | −2.3 (4) |
C23—O5—C21—C22 | −6.8 (4) | C7—C8—C13—C12 | 178.1 (2) |
C23—O5—C21—C20 | 175.5 (2) | C2—C3—C4—C25 | 173.6 (2) |
O2—C10—C9—C8 | 179.5 (2) | C2—C3—C4—C5 | −63.0 (2) |
C11—C10—C9—C8 | −1.2 (4) | C16—C2—C1—O1 | −3.8 (4) |
C13—C8—C9—C10 | 3.1 (4) | C3—C2—C1—O1 | 178.9 (3) |
C7—C8—C9—C10 | −177.3 (2) | C16—C2—C1—C6 | 177.4 (2) |
C1—C2—C16—C17 | 175.7 (3) | C3—C2—C1—C6 | 0.2 (3) |
C3—C2—C16—C17 | −7.2 (4) | C7—C6—C1—O1 | −0.3 (4) |
C1—C6—C7—C8 | −180.0 (2) | C5—C6—C1—O1 | 175.9 (3) |
C5—C6—C7—C8 | 4.1 (4) | C7—C6—C1—C2 | 178.5 (2) |
C13—C8—C7—C6 | −156.0 (3) | C5—C6—C1—C2 | −5.3 (4) |
C9—C8—C7—C6 | 24.4 (4) | C22—C17—C18—C19 | −1.2 (4) |
C2—C16—C17—C18 | −31.9 (4) | C16—C17—C18—C19 | −177.3 (2) |
C2—C16—C17—C22 | 152.0 (3) | O4—C20—C19—C18 | 178.2 (2) |
O5—C21—C22—C17 | −179.4 (2) | C21—C20—C19—C18 | −0.4 (4) |
C20—C21—C22—C17 | −1.8 (4) | C17—C18—C19—C20 | 0.5 (4) |
C18—C17—C22—C21 | 1.9 (4) | C3—C4—C25—C26 | −63.4 (3) |
C16—C17—C22—C21 | 178.2 (2) | C5—C4—C25—C26 | 175.0 (3) |
O3—C11—C12—C13 | −178.8 (2) | C7—C6—C5—C4 | 151.2 (3) |
C10—C11—C12—C13 | 2.4 (4) | C1—C6—C5—C4 | −24.7 (3) |
C16—C2—C3—C4 | −142.5 (3) | C25—C4—C5—C6 | −176.5 (2) |
C1—C2—C3—C4 | 34.5 (3) | C3—C4—C5—C6 | 58.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14B···O2i | 0.96 | 2.54 | 3.410 (3) | 151 |
Symmetry code: (i) −x+1/2, y−1/2, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | C26H30O5 |
Mr | 422.5 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 10.3766 (10), 8.6973 (9), 24.555 (3) |
β (°) | 93.500 (2) |
V (Å3) | 2212.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.21 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.983, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18534, 5285, 3034 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.182, 1.02 |
No. of reflections | 5285 |
No. of parameters | 285 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.19 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14B···O2i | 0.96 | 2.54 | 3.410 (3) | 151 |
Symmetry code: (i) −x+1/2, y−1/2, −z+5/2. |
Substituted 2,6-bis(benzylidenecyclohexanone) derivatives have been the subject of recent crystallographic investigations and have found useful applications as potent anti-cancer agents (Dimmock et al., 2001, 2005).
The six-membered cyclohexanone ring exists in an envelope conformation, the Cremer and Pople puckering parameters are Q(T) = 0.546 (2) Å, φ(2) = 172.5 (3)°, θ (2) = 57.3 (2)° (Cremer and Pople, 1975). The ring atom C24 deviates by +0.406 (6) Å from the least squares plane passing through C2/C4/C7/C8/C17. The C24 ring atom deviates by +0.406 (6) Å from the least squares plane passing through C2/C4/C7/C8/C17. Also the C6—C7—C8, 129.8 (2) and C2—C16—C17 130.2 (2) ° angles and the torsion angles about the C7—C8 24.4 (4) ° and C16—C17 - 31.9 (4)° bonds also deviate from planarity indicating significant steric repulsion between the aryl ring and the cyclohexanone ring, with repulsions in particular between the hydrogen atoms H18···H3B, 2.284 Å and H9···H5A 2.209 Å respectively. The crystal packing is stabilized by C—H···O intermolecular interactions forming C(7) molecular chains (Bernstein et al., 1995) along the crystallographic b axis.