Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029339/zl2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029339/zl2029Isup2.hkl |
CCDC reference: 655004
The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989). A solution of 25 g of NaOH in 250 ml of water and 200 ml of ethanol was placed in a 500 ml bolt head flask provided with a mechanical stirrer. The flask was immersed in a water bath and the temperature of the solution was maintained at 393–398 K. The solution was stirred vigorously and added to one half of a previously prepared mixture of 3,4-dimethoxybenzaldehyde (41.5 g, 0.25 mol) and cyclopentanone (10.5 g, 0.125 mol). A flocculent precipitate is formed within 5–10 minutes. After 25 minutes, the remainder of the aldehyde-cyclopentanone mixture was added and the stirring was continued for additional 45 minutes. The crude product obtained was filtered and washed with cold water to eliminate the NaOH as completely as possible. The compound was purified by crystallization from ethanol (yield: 65%). Single crystal were grown in a acetone-toluene mixture (2:8) by slow evaporation (m.p.: 398–403 K). Analysis for C23H24O5: Found (Calculated): C:72.55 (72.61); H: 6.29% (6.36%).
The H atoms were included in the riding model approximation with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.18–1.52Ueq(C).
The title compound, (I), 2,5-bis(3,4-dimethoxyphenyl)cyclopentanone, (synthesis; Fig. 3) is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely realted to the title compound is curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic in high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Certain curcumin analogs are described to be potent aldose reductase inhibitors (Du et al., 2006).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004), and related crystal and molecular structural studies of 2-(p-methylbenzyl)cyclopentanone and 2-(p-chlorobenzyl)-5-(p-bromobenzylidene)cyclopentanone (Theocharis et al., 1982) as well as one of the photodimerizable compound 5-benzylidene-2-(p-chlorobenzyl)cyclopentanone (Theocharis et al., 1981) and 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006) have been reported. In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound, (I), C23H24O5.
For the synthesis of the title compouund, see: Furniss et al. (1989). For biological activity of the title compound and curcumin, see: Du et al. (2006) and Reksohadiprodjo et al. (2004), respectively. For related structures, see: Girija et al. (2004); Theocharis et al. (1981, 1982); Butcher et al. (2006).
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C23H24O5 | F(000) = 808 |
Mr = 380.42 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9492 (9) Å | Cell parameters from 6322 reflections |
b = 8.8428 (10) Å | θ = 2.7–29.5° |
c = 27.603 (3) Å | µ = 0.09 mm−1 |
β = 92.421 (2)° | T = 173 K |
V = 1938.6 (4) Å3 | Plate, colorless |
Z = 4 | 0.50 × 0.48 × 0.27 mm |
Bruker APEX II CCD area-detector diffractometer | 5434 independent reflections |
Radiation source: fine-focus sealed tube | 4383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 30.1°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→10 |
Tmin = 0.861, Tmax = 1.000 | k = −9→12 |
21225 measured reflections | l = −37→37 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.4601P] where P = (Fo2 + 2Fc2)/3 |
5434 reflections | (Δ/σ)max = 0.001 |
257 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C23H24O5 | V = 1938.6 (4) Å3 |
Mr = 380.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.9492 (9) Å | µ = 0.09 mm−1 |
b = 8.8428 (10) Å | T = 173 K |
c = 27.603 (3) Å | 0.50 × 0.48 × 0.27 mm |
β = 92.421 (2)° |
Bruker APEX II CCD area-detector diffractometer | 5434 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 4383 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 1.000 | Rint = 0.025 |
21225 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.35 e Å−3 |
5434 reflections | Δρmin = −0.23 e Å−3 |
257 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 | 0.81476 (12) | 0.25378 (12) | 0.56791 (4) | 0.0441 (3) | |
O1A | 0.63787 (11) | −0.20756 (11) | 0.30071 (3) | 0.0363 (2) | |
O2A | 0.38946 (10) | −0.05138 (11) | 0.32971 (3) | 0.0360 (2) | |
O1B | 0.11569 (11) | 0.80398 (12) | 0.71096 (3) | 0.0394 (2) | |
O2B | 0.00659 (11) | 0.69043 (12) | 0.62888 (4) | 0.0416 (2) | |
C1 | 0.67617 (15) | 0.27066 (14) | 0.54724 (4) | 0.0292 (2) | |
C2 | 0.62053 (14) | 0.20262 (13) | 0.50019 (4) | 0.0264 (2) | |
C3 | 0.44328 (14) | 0.25268 (13) | 0.48725 (4) | 0.0263 (2) | |
H3A | 0.3677 | 0.1640 | 0.4836 | 0.032* | |
H3B | 0.4394 | 0.3096 | 0.4563 | 0.032* | |
C4 | 0.38814 (14) | 0.35517 (14) | 0.52927 (4) | 0.0264 (2) | |
H4A | 0.3577 | 0.4572 | 0.5170 | 0.032* | |
H4B | 0.2894 | 0.3112 | 0.5448 | 0.032* | |
C5 | 0.53647 (14) | 0.36409 (13) | 0.56496 (4) | 0.0264 (2) | |
C1A | 0.72554 (14) | 0.11349 (14) | 0.47582 (4) | 0.0289 (2) | |
H1AA | 0.8338 | 0.1006 | 0.4912 | 0.035* | |
C2A | 0.70094 (14) | 0.03375 (13) | 0.42997 (4) | 0.0261 (2) | |
C3A | 0.83432 (14) | −0.05166 (14) | 0.41327 (4) | 0.0300 (2) | |
H3AA | 0.9381 | −0.0537 | 0.4316 | 0.036* | |
C4A | 0.81865 (14) | −0.13364 (15) | 0.37044 (4) | 0.0305 (3) | |
H4AA | 0.9110 | −0.1913 | 0.3599 | 0.037* | |
C5A | 0.66858 (14) | −0.13152 (14) | 0.34312 (4) | 0.0282 (2) | |
C6A | 0.53173 (13) | −0.04561 (14) | 0.35913 (4) | 0.0270 (2) | |
C7A | 0.54844 (14) | 0.03504 (13) | 0.40180 (4) | 0.0269 (2) | |
H7AA | 0.4559 | 0.0924 | 0.4124 | 0.032* | |
C8A | 0.77269 (18) | −0.29440 (18) | 0.28243 (5) | 0.0421 (3) | |
H8AA | 0.7333 | −0.3476 | 0.2529 | 0.063* | |
H8AB | 0.8114 | −0.3682 | 0.3069 | 0.063* | |
H8AC | 0.8659 | −0.2270 | 0.2749 | 0.063* | |
C9A | 0.24621 (15) | 0.02963 (17) | 0.34540 (5) | 0.0369 (3) | |
H9AA | 0.1519 | 0.0158 | 0.3218 | 0.055* | |
H9AB | 0.2736 | 0.1374 | 0.3481 | 0.055* | |
H9AC | 0.2148 | −0.0088 | 0.3771 | 0.055* | |
C1B | 0.55581 (14) | 0.43827 (14) | 0.60739 (4) | 0.0287 (2) | |
H1BA | 0.6626 | 0.4251 | 0.6236 | 0.034* | |
C2B | 0.44034 (14) | 0.53533 (14) | 0.63258 (4) | 0.0270 (2) | |
C3B | 0.49604 (15) | 0.59992 (15) | 0.67642 (4) | 0.0321 (3) | |
H3BA | 0.6086 | 0.5825 | 0.6880 | 0.039* | |
C4B | 0.39165 (16) | 0.68903 (15) | 0.70360 (4) | 0.0332 (3) | |
H4BA | 0.4324 | 0.7299 | 0.7337 | 0.040* | |
C5B | 0.22851 (15) | 0.71848 (14) | 0.68699 (4) | 0.0301 (2) | |
C6B | 0.16958 (14) | 0.65609 (14) | 0.64237 (4) | 0.0291 (2) | |
C7B | 0.27334 (14) | 0.56639 (14) | 0.61594 (4) | 0.0278 (2) | |
H7BA | 0.2321 | 0.5247 | 0.5860 | 0.033* | |
C8B | 0.18210 (19) | 0.88207 (18) | 0.75296 (5) | 0.0444 (3) | |
H8BA | 0.0956 | 0.9491 | 0.7653 | 0.067* | |
H8BB | 0.2800 | 0.9421 | 0.7443 | 0.067* | |
H8BC | 0.2162 | 0.8085 | 0.7780 | 0.067* | |
C9B | −0.05314 (17) | 0.6372 (2) | 0.58261 (6) | 0.0497 (4) | |
H9BA | −0.1684 | 0.6733 | 0.5760 | 0.075* | |
H9BB | −0.0519 | 0.5264 | 0.5824 | 0.075* | |
H9BC | 0.0198 | 0.6754 | 0.5576 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0382 (5) | 0.0514 (6) | 0.0414 (5) | 0.0209 (4) | −0.0143 (4) | −0.0106 (5) |
O1A | 0.0337 (4) | 0.0433 (6) | 0.0320 (4) | 0.0100 (4) | 0.0021 (3) | −0.0113 (4) |
O2A | 0.0249 (4) | 0.0460 (6) | 0.0366 (5) | 0.0072 (4) | −0.0038 (3) | −0.0109 (4) |
O1B | 0.0330 (4) | 0.0439 (6) | 0.0415 (5) | −0.0023 (4) | 0.0055 (4) | −0.0180 (4) |
O2B | 0.0237 (4) | 0.0534 (6) | 0.0471 (5) | 0.0050 (4) | −0.0058 (4) | −0.0182 (5) |
C1 | 0.0311 (5) | 0.0274 (6) | 0.0287 (5) | 0.0075 (4) | −0.0035 (4) | 0.0006 (4) |
C2 | 0.0289 (5) | 0.0232 (5) | 0.0268 (5) | 0.0038 (4) | −0.0018 (4) | 0.0024 (4) |
C3 | 0.0252 (5) | 0.0264 (6) | 0.0272 (5) | 0.0014 (4) | −0.0003 (4) | −0.0008 (4) |
C4 | 0.0244 (5) | 0.0271 (6) | 0.0277 (5) | 0.0012 (4) | 0.0002 (4) | −0.0009 (4) |
C5 | 0.0275 (5) | 0.0246 (6) | 0.0269 (5) | 0.0039 (4) | −0.0015 (4) | 0.0034 (4) |
C1A | 0.0271 (5) | 0.0287 (6) | 0.0304 (6) | 0.0039 (4) | −0.0031 (4) | 0.0012 (5) |
C2A | 0.0251 (5) | 0.0243 (6) | 0.0290 (5) | 0.0032 (4) | 0.0014 (4) | 0.0018 (4) |
C3A | 0.0240 (5) | 0.0324 (6) | 0.0336 (6) | 0.0043 (4) | −0.0004 (4) | 0.0009 (5) |
C4A | 0.0253 (5) | 0.0336 (6) | 0.0330 (6) | 0.0063 (4) | 0.0055 (4) | −0.0005 (5) |
C5A | 0.0284 (5) | 0.0291 (6) | 0.0276 (5) | 0.0017 (4) | 0.0043 (4) | −0.0020 (4) |
C6A | 0.0221 (5) | 0.0288 (6) | 0.0300 (5) | 0.0015 (4) | 0.0003 (4) | 0.0002 (4) |
C7A | 0.0234 (5) | 0.0274 (6) | 0.0301 (5) | 0.0042 (4) | 0.0035 (4) | −0.0013 (4) |
C8A | 0.0437 (7) | 0.0458 (8) | 0.0373 (7) | 0.0151 (6) | 0.0081 (6) | −0.0077 (6) |
C9A | 0.0234 (5) | 0.0486 (8) | 0.0386 (7) | 0.0070 (5) | 0.0001 (5) | −0.0015 (6) |
C1B | 0.0287 (5) | 0.0302 (6) | 0.0267 (5) | 0.0056 (4) | −0.0050 (4) | 0.0023 (4) |
C2B | 0.0278 (5) | 0.0287 (6) | 0.0242 (5) | 0.0025 (4) | −0.0028 (4) | 0.0012 (4) |
C3B | 0.0305 (6) | 0.0374 (7) | 0.0276 (5) | 0.0040 (5) | −0.0078 (4) | −0.0016 (5) |
C4B | 0.0364 (6) | 0.0373 (7) | 0.0255 (5) | −0.0013 (5) | −0.0052 (5) | −0.0060 (5) |
C5B | 0.0303 (5) | 0.0296 (6) | 0.0305 (6) | −0.0031 (5) | 0.0027 (4) | −0.0054 (5) |
C6B | 0.0231 (5) | 0.0319 (6) | 0.0322 (6) | −0.0016 (4) | −0.0019 (4) | −0.0034 (5) |
C7B | 0.0271 (5) | 0.0303 (6) | 0.0257 (5) | −0.0008 (4) | −0.0027 (4) | −0.0036 (4) |
C8B | 0.0472 (8) | 0.0455 (8) | 0.0413 (7) | −0.0106 (6) | 0.0103 (6) | −0.0193 (6) |
C9B | 0.0262 (6) | 0.0704 (11) | 0.0513 (8) | 0.0032 (6) | −0.0120 (6) | −0.0175 (8) |
O1—C1 | 1.2282 (14) | C4A—H4AA | 0.9500 |
O1A—C5A | 1.3631 (14) | C5A—C6A | 1.4129 (15) |
O1A—C8A | 1.4278 (15) | C6A—C7A | 1.3787 (16) |
O2A—C6A | 1.3652 (14) | C7A—H7AA | 0.9500 |
O2A—C9A | 1.4280 (14) | C8A—H8AA | 0.9800 |
O1B—C5B | 1.3652 (15) | C8A—H8AB | 0.9800 |
O1B—C8B | 1.4310 (16) | C8A—H8AC | 0.9800 |
O2B—C6B | 1.3671 (14) | C9A—H9AA | 0.9800 |
O2B—C9B | 1.4236 (17) | C9A—H9AB | 0.9800 |
C1—C2 | 1.4819 (16) | C9A—H9AC | 0.9800 |
C1—C5 | 1.4836 (16) | C1B—C2B | 1.4548 (16) |
C2—C1A | 1.3483 (16) | C1B—H1BA | 0.9500 |
C2—C3 | 1.5054 (15) | C2B—C3B | 1.3933 (16) |
C3—C4 | 1.5498 (16) | C2B—C7B | 1.4133 (15) |
C3—H3A | 0.9900 | C3B—C4B | 1.3876 (18) |
C3—H3B | 0.9900 | C3B—H3BA | 0.9500 |
C4—C5 | 1.5064 (15) | C4B—C5B | 1.3819 (17) |
C4—H4A | 0.9900 | C4B—H4BA | 0.9500 |
C4—H4B | 0.9900 | C5B—C6B | 1.4114 (16) |
C5—C1B | 1.3454 (16) | C6B—C7B | 1.3758 (17) |
C1A—C2A | 1.4546 (16) | C7B—H7BA | 0.9500 |
C1A—H1AA | 0.9500 | C8B—H8BA | 0.9800 |
C2A—C3A | 1.3959 (16) | C8B—H8BB | 0.9800 |
C2A—C7A | 1.4123 (15) | C8B—H8BC | 0.9800 |
C3A—C4A | 1.3881 (17) | C9B—H9BA | 0.9800 |
C3A—H3AA | 0.9500 | C9B—H9BB | 0.9800 |
C4A—C5A | 1.3842 (16) | C9B—H9BC | 0.9800 |
C5A—O1A—C8A | 117.32 (10) | O1A—C8A—H8AA | 109.5 |
C6A—O2A—C9A | 116.87 (9) | O1A—C8A—H8AB | 109.5 |
C5B—O1B—C8B | 115.62 (10) | H8AA—C8A—H8AB | 109.5 |
C6B—O2B—C9B | 116.58 (10) | O1A—C8A—H8AC | 109.5 |
O1—C1—C2 | 125.91 (11) | H8AA—C8A—H8AC | 109.5 |
O1—C1—C5 | 125.71 (11) | H8AB—C8A—H8AC | 109.5 |
C2—C1—C5 | 108.38 (9) | O2A—C9A—H9AA | 109.5 |
C1A—C2—C1 | 120.43 (10) | O2A—C9A—H9AB | 109.5 |
C1A—C2—C3 | 130.28 (11) | H9AA—C9A—H9AB | 109.5 |
C1—C2—C3 | 109.29 (9) | O2A—C9A—H9AC | 109.5 |
C2—C3—C4 | 106.61 (9) | H9AA—C9A—H9AC | 109.5 |
C2—C3—H3A | 110.4 | H9AB—C9A—H9AC | 109.5 |
C4—C3—H3A | 110.4 | C5—C1B—C2B | 130.72 (10) |
C2—C3—H3B | 110.4 | C5—C1B—H1BA | 114.6 |
C4—C3—H3B | 110.4 | C2B—C1B—H1BA | 114.6 |
H3A—C3—H3B | 108.6 | C3B—C2B—C7B | 117.53 (10) |
C5—C4—C3 | 106.37 (9) | C3B—C2B—C1B | 118.24 (10) |
C5—C4—H4A | 110.5 | C7B—C2B—C1B | 124.22 (10) |
C3—C4—H4A | 110.5 | C4B—C3B—C2B | 121.82 (11) |
C5—C4—H4B | 110.5 | C4B—C3B—H3BA | 119.1 |
C3—C4—H4B | 110.5 | C2B—C3B—H3BA | 119.1 |
H4A—C4—H4B | 108.6 | C5B—C4B—C3B | 120.12 (11) |
C1B—C5—C1 | 119.93 (10) | C5B—C4B—H4BA | 119.9 |
C1B—C5—C4 | 130.72 (10) | C3B—C4B—H4BA | 119.9 |
C1—C5—C4 | 109.34 (10) | O1B—C5B—C4B | 124.75 (11) |
C2—C1A—C2A | 130.85 (11) | O1B—C5B—C6B | 116.03 (11) |
C2—C1A—H1AA | 114.6 | C4B—C5B—C6B | 119.22 (11) |
C2A—C1A—H1AA | 114.6 | O2B—C6B—C7B | 124.47 (11) |
C3A—C2A—C7A | 117.96 (10) | O2B—C6B—C5B | 115.27 (10) |
C3A—C2A—C1A | 118.26 (10) | C7B—C6B—C5B | 120.26 (10) |
C7A—C2A—C1A | 123.76 (10) | C6B—C7B—C2B | 121.04 (10) |
C4A—C3A—C2A | 121.45 (11) | C6B—C7B—H7BA | 119.5 |
C4A—C3A—H3AA | 119.3 | C2B—C7B—H7BA | 119.5 |
C2A—C3A—H3AA | 119.3 | O1B—C8B—H8BA | 109.5 |
C5A—C4A—C3A | 120.08 (10) | O1B—C8B—H8BB | 109.5 |
C5A—C4A—H4AA | 120.0 | H8BA—C8B—H8BB | 109.5 |
C3A—C4A—H4AA | 120.0 | O1B—C8B—H8BC | 109.5 |
O1A—C5A—C4A | 125.46 (10) | H8BA—C8B—H8BC | 109.5 |
O1A—C5A—C6A | 114.93 (10) | H8BB—C8B—H8BC | 109.5 |
C4A—C5A—C6A | 119.61 (11) | O2B—C9B—H9BA | 109.5 |
O2A—C6A—C7A | 125.11 (10) | O2B—C9B—H9BB | 109.5 |
O2A—C6A—C5A | 115.04 (10) | H9BA—C9B—H9BB | 109.5 |
C7A—C6A—C5A | 119.85 (10) | O2B—C9B—H9BC | 109.5 |
C6A—C7A—C2A | 121.04 (10) | H9BA—C9B—H9BC | 109.5 |
C6A—C7A—H7AA | 119.5 | H9BB—C9B—H9BC | 109.5 |
C2A—C7A—H7AA | 119.5 | ||
O1—C1—C2—C1A | −0.3 (2) | O1A—C5A—C6A—C7A | 179.55 (11) |
C5—C1—C2—C1A | 179.10 (11) | C4A—C5A—C6A—C7A | −0.16 (18) |
O1—C1—C2—C3 | −179.31 (13) | O2A—C6A—C7A—C2A | 179.80 (11) |
C5—C1—C2—C3 | 0.12 (13) | C5A—C6A—C7A—C2A | 0.17 (18) |
C1A—C2—C3—C4 | −179.60 (12) | C3A—C2A—C7A—C6A | 0.02 (17) |
C1—C2—C3—C4 | −0.75 (13) | C1A—C2A—C7A—C6A | −178.56 (11) |
C2—C3—C4—C5 | 1.09 (12) | C1—C5—C1B—C2B | −179.78 (12) |
O1—C1—C5—C1B | −0.6 (2) | C4—C5—C1B—C2B | −0.6 (2) |
C2—C1—C5—C1B | 179.94 (11) | C5—C1B—C2B—C3B | −179.06 (13) |
O1—C1—C5—C4 | −179.98 (13) | C5—C1B—C2B—C7B | 2.2 (2) |
C2—C1—C5—C4 | 0.59 (13) | C7B—C2B—C3B—C4B | 1.34 (19) |
C3—C4—C5—C1B | 179.71 (12) | C1B—C2B—C3B—C4B | −177.47 (12) |
C3—C4—C5—C1 | −1.04 (13) | C2B—C3B—C4B—C5B | −1.3 (2) |
C1—C2—C1A—C2A | 179.44 (12) | C8B—O1B—C5B—C4B | 8.17 (19) |
C3—C2—C1A—C2A | −1.8 (2) | C8B—O1B—C5B—C6B | −172.51 (12) |
C2—C1A—C2A—C3A | −179.99 (13) | C3B—C4B—C5B—O1B | 179.72 (12) |
C2—C1A—C2A—C7A | −1.4 (2) | C3B—C4B—C5B—C6B | 0.4 (2) |
C7A—C2A—C3A—C4A | −0.23 (18) | C9B—O2B—C6B—C7B | −4.6 (2) |
C1A—C2A—C3A—C4A | 178.44 (11) | C9B—O2B—C6B—C5B | 176.11 (13) |
C2A—C3A—C4A—C5A | 0.24 (19) | O1B—C5B—C6B—O2B | 0.33 (17) |
C8A—O1A—C5A—C4A | −1.26 (19) | C4B—C5B—C6B—O2B | 179.69 (12) |
C8A—O1A—C5A—C6A | 179.05 (11) | O1B—C5B—C6B—C7B | −179.01 (11) |
C3A—C4A—C5A—O1A | −179.72 (12) | C4B—C5B—C6B—C7B | 0.35 (19) |
C3A—C4A—C5A—C6A | −0.04 (18) | O2B—C6B—C7B—C2B | −179.56 (12) |
C9A—O2A—C6A—C7A | −1.76 (18) | C5B—C6B—C7B—C2B | −0.28 (19) |
C9A—O2A—C6A—C5A | 177.88 (11) | C3B—C2B—C7B—C6B | −0.54 (18) |
O1A—C5A—C6A—O2A | −0.11 (16) | C1B—C2B—C7B—C6B | 178.18 (12) |
C4A—C5A—C6A—O2A | −179.82 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4BA···O1Ai | 0.95 | 2.42 | 3.2556 (15) | 146 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H24O5 |
Mr | 380.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 7.9492 (9), 8.8428 (10), 27.603 (3) |
β (°) | 92.421 (2) |
V (Å3) | 1938.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.48 × 0.27 |
Data collection | |
Diffractometer | Bruker APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.861, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21225, 5434, 4383 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.128, 1.02 |
No. of reflections | 5434 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.23 |
Computer programs: APEX2 (Bruker, 2006), APEX2, SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4BA···O1Ai | 0.95 | 2.42 | 3.2556 (15) | 146.1 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
The title compound, (I), 2,5-bis(3,4-dimethoxyphenyl)cyclopentanone, (synthesis; Fig. 3) is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely realted to the title compound is curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic in high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Certain curcumin analogs are described to be potent aldose reductase inhibitors (Du et al., 2006).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004), and related crystal and molecular structural studies of 2-(p-methylbenzyl)cyclopentanone and 2-(p-chlorobenzyl)-5-(p-bromobenzylidene)cyclopentanone (Theocharis et al., 1982) as well as one of the photodimerizable compound 5-benzylidene-2-(p-chlorobenzyl)cyclopentanone (Theocharis et al., 1981) and 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006) have been reported. In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound, (I), C23H24O5.