Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053032/cv2324sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053032/cv2324Isup2.hkl |
CCDC reference: 667486
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.008 Å
- R factor = 0.040
- wR factor = 0.115
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check
For details of structure–activity correlations in related 3,5-bis(arylidene)-4-piperidones, see: Dimmock et al. (2001). For details of highly active curcumin derivatives used as anti-cancer agents, see: Dimmock et al. (2005). For details of conformational analysis in organic molecules, see: Cremer & Pople (1975).
An aqueous solution of sodium hydroxide (10% w/v, 30 ml) was added to a solution of 1-naphthaldehyde (2.7 ml, 0.02 mol) and /g-methylcyclohexanone (1.3 mL, 0.01 mol) in ethanol (50 ml). The reaction mixture was stirred at 10–20 °C for 2 h and left overnight in an ice chest to get a yellow coloured solid. The product was filtered, washed with ice-cold water (100 ml) followed by ice-cold ethanol (20 ml), dried and recrystallized from DMF. Yield: 78%, m.p.: 172–173%C.
All H atoms were geometrically positioned (C—H 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C).
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).
In the title compound (Fig. 1), the six-membered cyclohexanone ring exists in an envelope conformation, the Cremer and Pople puckering parameters are Q(T) = 0.414 (6) Å, φ(2) = 166.2 (12)°, θ (2) = 40.8 (8)° (Cremer and Pople, 1975). Atom C4 deviates at -0.541 (6) Å from the least squares plane C1/C2/C3/C5/C6. Two bicycles make a dihedral angle of 46.1 (1)°.
The crystal structure is stabilized by van-der Waals interactions.
For details of structure–activity correlations in related 3,5-bis(arylidene)-4-piperidones, see: Dimmock et al. (2001). For details of highly active curcumin derivatives used as anti-cancer agents, see: Dimmock et al. (2005). For details of conformational analysis in organic molecules, see: 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: CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. Molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. |
C29H24O | F(000) = 824 |
Mr = 388.48 | Dx = 1.198 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4081 reflections |
a = 14.5282 (19) Å | θ = 1.8–20.8° |
b = 10.3604 (14) Å | µ = 0.07 mm−1 |
c = 14.708 (2) Å | T = 290 K |
β = 103.312 (3)° | Blocks, yellow |
V = 2154.3 (5) Å3 | 0.25 × 0.21 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2777 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 25.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −17→17 |
Tmin = 0.936, Tmax = 0.986 | k = −12→12 |
16027 measured reflections | l = −17→17 |
4081 independent reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.2955P] where P = (Fo2 + 2Fc2)/3 |
4081 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C29H24O | V = 2154.3 (5) Å3 |
Mr = 388.48 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.5282 (19) Å | µ = 0.07 mm−1 |
b = 10.3604 (14) Å | T = 290 K |
c = 14.708 (2) Å | 0.25 × 0.21 × 0.20 mm |
β = 103.312 (3)° |
Bruker SMART CCD area-detector diffractometer | 4081 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2777 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.986 | Rint = 0.060 |
16027 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.31 e Å−3 |
4081 reflections | Δρmin = −0.20 e Å−3 |
272 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 | ||
O1 | 0.3468 (3) | 0.0948 (3) | 0.0205 (3) | 0.0639 (11) | |
C1 | 0.4037 (3) | 0.0337 (5) | 0.0777 (3) | 0.0412 (12) | |
C2 | 0.4101 (3) | −0.1100 (5) | 0.0694 (3) | 0.0394 (11) | |
C3 | 0.4969 (4) | −0.1763 (5) | 0.1248 (4) | 0.0552 (14) | |
C4 | 0.5323 (4) | −0.1192 (5) | 0.2193 (4) | 0.0662 (17) | |
C5 | 0.5494 (4) | 0.0216 (5) | 0.2167 (4) | 0.0653 (17) | |
C6 | 0.4692 (3) | 0.0994 (5) | 0.1582 (3) | 0.0421 (12) | |
C7 | 0.3361 (3) | −0.1704 (5) | 0.0189 (3) | 0.0461 (13) | |
C8 | 0.3266 (4) | −0.3101 (5) | −0.0015 (3) | 0.0450 (13) | |
C9 | 0.3891 (4) | −0.3702 (6) | −0.0443 (4) | 0.0616 (15) | |
C10 | 0.3796 (5) | −0.4999 (6) | −0.0696 (4) | 0.0718 (18) | |
C11 | 0.3085 (5) | −0.5711 (5) | −0.0505 (4) | 0.0683 (18) | |
C12 | 0.2428 (4) | −0.5160 (5) | −0.0046 (3) | 0.0538 (15) | |
C13 | 0.1679 (5) | −0.5875 (6) | 0.0172 (4) | 0.0755 (19) | |
C14 | 0.1065 (6) | −0.5327 (7) | 0.0625 (5) | 0.088 (2) | |
C15 | 0.1150 (5) | −0.4025 (7) | 0.0865 (5) | 0.081 (2) | |
C16 | 0.1852 (4) | −0.3292 (6) | 0.0664 (4) | 0.0585 (15) | |
C17 | 0.2509 (4) | −0.3836 (5) | 0.0200 (3) | 0.0462 (13) | |
C18 | 0.4495 (3) | 0.2222 (5) | 0.1732 (3) | 0.0408 (12) | |
C19 | 0.4976 (4) | 0.3126 (5) | 0.2461 (3) | 0.0440 (12) | |
C20 | 0.5936 (4) | 0.3138 (5) | 0.2784 (4) | 0.0541 (14) | |
C21 | 0.6382 (4) | 0.4012 (6) | 0.3464 (4) | 0.0644 (16) | |
C22 | 0.5872 (5) | 0.4890 (6) | 0.3820 (4) | 0.0700 (18) | |
C23 | 0.4884 (4) | 0.4944 (5) | 0.3510 (4) | 0.0568 (15) | |
C24 | 0.4337 (5) | 0.5854 (7) | 0.3875 (5) | 0.084 (2) | |
C25 | 0.3390 (6) | 0.5889 (7) | 0.3578 (5) | 0.087 (2) | |
C26 | 0.2932 (5) | 0.5019 (6) | 0.2914 (5) | 0.0755 (19) | |
C27 | 0.3427 (4) | 0.4130 (5) | 0.2546 (4) | 0.0562 (14) | |
C28 | 0.4417 (4) | 0.4056 (5) | 0.2825 (3) | 0.0465 (13) | |
C29 | 0.6199 (5) | −0.1892 (6) | 0.2752 (5) | 0.095 (2) | |
H3A | 0.4827 | −0.2667 | 0.1315 | 0.066* | |
H3B | 0.5464 | −0.1713 | 0.0906 | 0.066* | |
H4 | 0.4823 | −0.1313 | 0.2532 | 0.079* | |
H5A | 0.6055 | 0.0357 | 0.1928 | 0.078* | |
H5B | 0.5626 | 0.0544 | 0.2801 | 0.078* | |
H7 | 0.2839 | −0.1195 | −0.0069 | 0.055* | |
H9 | 0.4392 | −0.3232 | −0.0569 | 0.074* | |
H10 | 0.4224 | −0.5376 | −0.0998 | 0.086* | |
H11 | 0.3028 | −0.6576 | −0.0678 | 0.082* | |
H13 | 0.1605 | −0.6739 | 0.0000 | 0.091* | |
H14 | 0.0586 | −0.5821 | 0.0775 | 0.106* | |
H15 | 0.0720 | −0.3653 | 0.1167 | 0.098* | |
H16 | 0.1901 | −0.2426 | 0.0833 | 0.070* | |
H18 | 0.3973 | 0.2560 | 0.1311 | 0.049* | |
H20 | 0.6301 | 0.2549 | 0.2544 | 0.065* | |
H21 | 0.7036 | 0.3991 | 0.3675 | 0.077* | |
H22 | 0.6179 | 0.5465 | 0.4275 | 0.084* | |
H24 | 0.4638 | 0.6437 | 0.4328 | 0.101* | |
H27 | 0.3103 | 0.3556 | 0.2099 | 0.067* | |
H25 | 0.3043 | 0.6500 | 0.3819 | 0.105* | |
H26 | 0.2277 | 0.5045 | 0.2717 | 0.091* | |
H29A | 0.6097 | −0.2808 | 0.2703 | 0.143* | |
H29B | 0.6313 | −0.1638 | 0.3396 | 0.143* | |
H29C | 0.6737 | −0.1671 | 0.2508 | 0.143* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.071 (3) | 0.040 (2) | 0.064 (2) | 0.0018 (19) | −0.019 (2) | 0.0077 (19) |
C1 | 0.042 (3) | 0.041 (3) | 0.041 (3) | −0.004 (2) | 0.011 (2) | 0.005 (2) |
C2 | 0.038 (3) | 0.042 (3) | 0.037 (3) | 0.002 (2) | 0.004 (2) | −0.002 (2) |
C3 | 0.059 (4) | 0.046 (3) | 0.058 (3) | −0.001 (3) | 0.009 (3) | −0.007 (3) |
C4 | 0.077 (4) | 0.046 (4) | 0.065 (4) | 0.007 (3) | −0.005 (3) | 0.001 (3) |
C5 | 0.066 (4) | 0.055 (4) | 0.062 (4) | 0.000 (3) | −0.010 (3) | −0.002 (3) |
C6 | 0.044 (3) | 0.035 (3) | 0.048 (3) | −0.002 (2) | 0.011 (2) | 0.000 (2) |
C7 | 0.042 (3) | 0.044 (3) | 0.049 (3) | 0.004 (2) | 0.005 (2) | 0.001 (2) |
C8 | 0.049 (3) | 0.037 (3) | 0.041 (3) | 0.002 (2) | −0.006 (2) | −0.001 (2) |
C9 | 0.058 (4) | 0.054 (4) | 0.071 (4) | 0.003 (3) | 0.011 (3) | −0.007 (3) |
C10 | 0.078 (5) | 0.058 (4) | 0.081 (4) | 0.009 (4) | 0.021 (4) | −0.019 (3) |
C11 | 0.096 (5) | 0.031 (3) | 0.069 (4) | 0.016 (3) | 0.000 (4) | −0.009 (3) |
C12 | 0.073 (4) | 0.037 (3) | 0.042 (3) | −0.008 (3) | −0.006 (3) | 0.000 (2) |
C13 | 0.103 (5) | 0.053 (4) | 0.062 (4) | −0.027 (4) | 0.001 (4) | 0.002 (3) |
C14 | 0.101 (6) | 0.085 (6) | 0.080 (5) | −0.047 (5) | 0.024 (4) | −0.001 (4) |
C15 | 0.083 (5) | 0.088 (5) | 0.080 (5) | −0.023 (4) | 0.032 (4) | −0.011 (4) |
C16 | 0.068 (4) | 0.056 (4) | 0.050 (3) | −0.010 (3) | 0.009 (3) | −0.009 (3) |
C17 | 0.056 (3) | 0.045 (3) | 0.030 (2) | −0.005 (3) | −0.008 (2) | −0.003 (2) |
C18 | 0.032 (3) | 0.043 (3) | 0.046 (3) | −0.004 (2) | 0.005 (2) | 0.002 (2) |
C19 | 0.051 (3) | 0.032 (3) | 0.046 (3) | −0.006 (2) | 0.006 (2) | 0.006 (2) |
C20 | 0.047 (3) | 0.046 (3) | 0.065 (4) | −0.002 (3) | 0.004 (3) | 0.002 (3) |
C21 | 0.052 (4) | 0.055 (4) | 0.073 (4) | −0.009 (3) | −0.011 (3) | −0.001 (3) |
C22 | 0.081 (5) | 0.053 (4) | 0.063 (4) | −0.019 (3) | −0.011 (3) | −0.015 (3) |
C23 | 0.070 (4) | 0.043 (3) | 0.054 (3) | −0.005 (3) | 0.006 (3) | −0.006 (3) |
C24 | 0.096 (6) | 0.071 (5) | 0.077 (5) | −0.003 (4) | 0.000 (4) | −0.029 (4) |
C25 | 0.104 (6) | 0.070 (5) | 0.087 (5) | 0.021 (4) | 0.021 (4) | −0.018 (4) |
C26 | 0.071 (4) | 0.073 (4) | 0.081 (4) | 0.014 (4) | 0.012 (4) | −0.008 (4) |
C27 | 0.064 (4) | 0.047 (3) | 0.055 (3) | 0.002 (3) | 0.008 (3) | −0.005 (3) |
C28 | 0.054 (3) | 0.036 (3) | 0.047 (3) | −0.004 (2) | 0.005 (2) | 0.008 (2) |
C29 | 0.109 (6) | 0.061 (4) | 0.085 (5) | 0.022 (4) | −0.039 (4) | 0.001 (4) |
O1—C1 | 1.213 (5) | C5—H5B | 0.9700 |
C28—C27 | 1.404 (7) | C3—C4 | 1.488 (7) |
C28—C23 | 1.416 (7) | C3—H3A | 0.9700 |
C28—C19 | 1.441 (7) | C3—H3B | 0.9700 |
C17—C16 | 1.412 (7) | C4—C29 | 1.530 (7) |
C17—C12 | 1.417 (7) | C4—H4 | 0.9800 |
C17—C8 | 1.432 (7) | C20—C21 | 1.394 (7) |
C1—C2 | 1.498 (7) | C20—H20 | 0.9300 |
C1—C6 | 1.501 (6) | C9—C10 | 1.392 (8) |
C7—C2 | 1.316 (6) | C9—H9 | 0.9300 |
C7—C8 | 1.478 (7) | C23—C22 | 1.403 (8) |
C7—H7 | 0.9300 | C23—C24 | 1.417 (8) |
C2—C3 | 1.502 (6) | C13—C14 | 1.355 (9) |
C8—C9 | 1.368 (7) | C13—H13 | 0.9300 |
C12—C11 | 1.411 (8) | C21—C22 | 1.353 (8) |
C12—C13 | 1.413 (8) | C21—H21 | 0.9300 |
C6—C18 | 1.334 (6) | C22—H22 | 0.9300 |
C6—C5 | 1.512 (7) | C24—C25 | 1.345 (9) |
C19—C20 | 1.365 (7) | C24—H24 | 0.9300 |
C19—C18 | 1.474 (6) | C14—C15 | 1.393 (9) |
C18—H18 | 0.9300 | C14—H14 | 0.9300 |
C16—C15 | 1.358 (8) | C25—C26 | 1.381 (9) |
C16—H16 | 0.9300 | C25—H25 | 0.9300 |
C11—C10 | 1.351 (8) | C26—H26 | 0.9300 |
C11—H11 | 0.9300 | C29—H29A | 0.9600 |
C27—C26 | 1.355 (8) | C29—H29B | 0.9600 |
C27—H27 | 0.9300 | C29—H29C | 0.9600 |
C5—C4 | 1.482 (8) | C15—H15 | 0.9300 |
C5—H5A | 0.9700 | C10—H10 | 0.9300 |
C27—C28—C23 | 117.6 (5) | H3A—C3—H3B | 107.8 |
C27—C28—C19 | 123.8 (5) | C5—C4—C3 | 113.0 (5) |
C23—C28—C19 | 118.6 (5) | C5—C4—C29 | 110.9 (5) |
C16—C17—C12 | 118.9 (5) | C3—C4—C29 | 112.3 (5) |
C16—C17—C8 | 122.3 (5) | C5—C4—H4 | 106.7 |
C12—C17—C8 | 118.8 (5) | C3—C4—H4 | 106.7 |
O1—C1—C2 | 120.5 (4) | C29—C4—H4 | 106.7 |
O1—C1—C6 | 121.1 (4) | C19—C20—C21 | 121.6 (5) |
C2—C1—C6 | 118.4 (4) | C19—C20—H20 | 119.2 |
C2—C7—C8 | 127.3 (5) | C21—C20—H20 | 119.2 |
C2—C7—H7 | 116.3 | C8—C9—C10 | 121.8 (6) |
C8—C7—H7 | 116.3 | C8—C9—H9 | 119.1 |
C7—C2—C1 | 117.5 (4) | C10—C9—H9 | 119.1 |
C7—C2—C3 | 124.3 (5) | C22—C23—C28 | 119.5 (5) |
C1—C2—C3 | 118.1 (4) | C22—C23—C24 | 121.6 (6) |
C9—C8—C17 | 119.0 (5) | C28—C23—C24 | 118.9 (6) |
C9—C8—C7 | 119.9 (5) | C14—C13—C12 | 121.4 (6) |
C17—C8—C7 | 121.0 (5) | C14—C13—H13 | 119.3 |
C11—C12—C13 | 122.6 (6) | C12—C13—H13 | 119.3 |
C11—C12—C17 | 119.2 (5) | C22—C21—C20 | 120.6 (5) |
C13—C12—C17 | 118.2 (6) | C22—C21—H21 | 119.7 |
C18—C6—C1 | 116.2 (4) | C20—C21—H21 | 119.7 |
C18—C6—C5 | 125.5 (5) | C21—C22—C23 | 120.8 (5) |
C1—C6—C5 | 118.2 (4) | C21—C22—H22 | 119.6 |
C20—C19—C28 | 118.9 (5) | C23—C22—H22 | 119.6 |
C20—C19—C18 | 122.3 (5) | C25—C24—C23 | 121.0 (6) |
C28—C19—C18 | 118.8 (4) | C25—C24—H24 | 119.5 |
C6—C18—C19 | 130.0 (5) | C23—C24—H24 | 119.5 |
C6—C18—H18 | 115.0 | C13—C14—C15 | 120.0 (6) |
C19—C18—H18 | 115.0 | C13—C14—H14 | 120.0 |
C15—C16—C17 | 120.5 (6) | C15—C14—H14 | 120.0 |
C15—C16—H16 | 119.8 | C24—C25—C26 | 120.2 (6) |
C17—C16—H16 | 119.8 | C24—C25—H25 | 119.9 |
C10—C11—C12 | 120.9 (5) | C26—C25—H25 | 119.9 |
C10—C11—H11 | 119.6 | C27—C26—C25 | 120.8 (6) |
C12—C11—H11 | 119.6 | C27—C26—H26 | 119.6 |
C26—C27—C28 | 121.5 (5) | C25—C26—H26 | 119.6 |
C26—C27—H27 | 119.3 | C4—C29—H29A | 109.5 |
C28—C27—H27 | 119.3 | C4—C29—H29B | 109.5 |
C4—C5—C6 | 115.3 (5) | H29A—C29—H29B | 109.5 |
C4—C5—H5A | 108.5 | C4—C29—H29C | 109.5 |
C6—C5—H5A | 108.5 | H29A—C29—H29C | 109.5 |
C4—C5—H5B | 108.5 | H29B—C29—H29C | 109.5 |
C6—C5—H5B | 108.5 | C16—C15—C14 | 120.9 (7) |
H5A—C5—H5B | 107.5 | C16—C15—H15 | 119.5 |
C4—C3—C2 | 113.1 (4) | C14—C15—H15 | 119.5 |
C4—C3—H3A | 109.0 | C11—C10—C9 | 120.3 (6) |
C2—C3—H3A | 109.0 | C11—C10—H10 | 119.8 |
C4—C3—H3B | 109.0 | C9—C10—H10 | 119.8 |
C2—C3—H3B | 109.0 | ||
C8—C7—C2—C1 | 178.2 (5) | C19—C28—C27—C26 | 179.6 (5) |
C8—C7—C2—C3 | −6.7 (8) | C18—C6—C5—C4 | 150.9 (5) |
O1—C1—C2—C7 | −20.8 (7) | C1—C6—C5—C4 | −27.3 (7) |
C6—C1—C2—C7 | 159.1 (4) | C7—C2—C3—C4 | −137.2 (5) |
O1—C1—C2—C3 | 163.7 (5) | C1—C2—C3—C4 | 37.9 (7) |
C6—C1—C2—C3 | −16.4 (6) | C6—C5—C4—C3 | 49.4 (8) |
C16—C17—C8—C9 | 178.2 (5) | C6—C5—C4—C29 | 176.5 (5) |
C12—C17—C8—C9 | −0.5 (7) | C2—C3—C4—C5 | −54.4 (7) |
C16—C17—C8—C7 | −3.9 (7) | C2—C3—C4—C29 | 179.1 (5) |
C12—C17—C8—C7 | 177.4 (4) | C28—C19—C20—C21 | 1.1 (8) |
C2—C7—C8—C9 | −57.8 (7) | C18—C19—C20—C21 | 179.0 (5) |
C2—C7—C8—C17 | 124.4 (6) | C17—C8—C9—C10 | 1.6 (8) |
C16—C17—C12—C11 | −179.7 (5) | C7—C8—C9—C10 | −176.3 (5) |
C8—C17—C12—C11 | −0.9 (7) | C27—C28—C23—C22 | 178.9 (5) |
C16—C17—C12—C13 | 1.1 (7) | C19—C28—C23—C22 | −0.4 (8) |
C8—C17—C12—C13 | 179.9 (5) | C27—C28—C23—C24 | −0.1 (8) |
O1—C1—C6—C18 | 12.2 (7) | C19—C28—C23—C24 | −179.5 (5) |
C2—C1—C6—C18 | −167.7 (4) | C11—C12—C13—C14 | 179.1 (6) |
O1—C1—C6—C5 | −169.4 (5) | C17—C12—C13—C14 | −1.7 (9) |
C2—C1—C6—C5 | 10.8 (7) | C19—C20—C21—C22 | −0.7 (9) |
C27—C28—C19—C20 | −179.8 (5) | C20—C21—C22—C23 | −0.3 (9) |
C23—C28—C19—C20 | −0.5 (7) | C28—C23—C22—C21 | 0.8 (9) |
C27—C28—C19—C18 | 2.2 (7) | C24—C23—C22—C21 | 179.9 (6) |
C23—C28—C19—C18 | −178.5 (4) | C22—C23—C24—C25 | −179.5 (7) |
C1—C6—C18—C19 | 178.7 (4) | C28—C23—C24—C25 | −0.4 (10) |
C5—C6—C18—C19 | 0.5 (8) | C12—C13—C14—C15 | 1.7 (10) |
C20—C19—C18—C6 | 36.9 (8) | C23—C24—C25—C26 | 0.8 (11) |
C28—C19—C18—C6 | −145.1 (5) | C28—C27—C26—C25 | 0.1 (9) |
C12—C17—C16—C15 | −0.5 (8) | C24—C25—C26—C27 | −0.7 (11) |
C8—C17—C16—C15 | −179.2 (5) | C17—C16—C15—C14 | 0.4 (10) |
C13—C12—C11—C10 | −179.6 (6) | C13—C14—C15—C16 | −1.0 (11) |
C17—C12—C11—C10 | 1.2 (8) | C12—C11—C10—C9 | −0.1 (9) |
C23—C28—C27—C26 | 0.3 (8) | C8—C9—C10—C11 | −1.3 (9) |
Experimental details
Crystal data | |
Chemical formula | C29H24O |
Mr | 388.48 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 290 |
a, b, c (Å) | 14.5282 (19), 10.3604 (14), 14.708 (2) |
β (°) | 103.312 (3) |
V (Å3) | 2154.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
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 | 0.936, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16027, 4081, 2777 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.115, 1.02 |
No. of reflections | 4081 |
No. of parameters | 272 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.20 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
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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).
In the title compound (Fig. 1), the six-membered cyclohexanone ring exists in an envelope conformation, the Cremer and Pople puckering parameters are Q(T) = 0.414 (6) Å, φ(2) = 166.2 (12)°, θ (2) = 40.8 (8)° (Cremer and Pople, 1975). Atom C4 deviates at -0.541 (6) Å from the least squares plane C1/C2/C3/C5/C6. Two bicycles make a dihedral angle of 46.1 (1)°.
The crystal structure is stabilized by van-der Waals interactions.