Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026888/cv2246sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026888/cv2246Isup2.hkl |
CCDC reference: 654883
Key indicators
- Single-crystal X-ray study
- T = 103 K
- Mean (C-C) = 0.001 Å
- R factor = 0.041
- wR factor = 0.114
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
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Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 20
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ...Each of the authors listed made significant contributions to this paper. Thank you for your consideration. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004). For hydrogen-bonding interactions and related structures, see: Girija et al. (2004) and Butcher et al. (2006). For related literature, see: Author? (1989).
The title compound was synthesized with a yield of 75% according to the method reported in Author? (1989). The compound was purified by recrystallization from ethanol. The crystal was grown in acetone:toluene [50:50] solvent by the slow evaporation technique (m.p.:368–373 K). Analysis for C21H22O5: Found (Calculated): C: 71.20 (71.17%); H: 6.18 (6.22%).
The H atoms were included in calculated positions (C—H 0.95–0.98 Å) and refined in riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).
The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related 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 at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.
For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004). For hydrogen-bonding interactions and related structures, see: Girija et al. (2004) and Butcher et al. (2006). For related literature, see: Author? (1989).
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).
C21H22O5 | F(000) = 1504 |
Mr = 354.39 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.1646 (13) Å | Cell parameters from 7695 reflections |
b = 7.7488 (5) Å | θ = 2.8–29.6° |
c = 24.8495 (17) Å | µ = 0.09 mm−1 |
β = 100.414 (1)° | T = 103 K |
V = 3629.4 (4) Å3 | Prism, colourless |
Z = 8 | 0.56 × 0.35 × 0.24 mm |
CCD area-detector diffractometer | 10146 independent reflections |
Radiation source: fine-focus sealed tube | 8569 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 29.7°, θmin = 1.7° |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | h = −26→26 |
Tmin = 0.950, Tmax = 0.988 | k = −10→10 |
40342 measured reflections | l = −33→34 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.9436P] where P = (Fo2 + 2Fc2)/3 |
10146 reflections | (Δ/σ)max = 0.002 |
477 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C21H22O5 | V = 3629.4 (4) Å3 |
Mr = 354.39 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.1646 (13) Å | µ = 0.09 mm−1 |
b = 7.7488 (5) Å | T = 103 K |
c = 24.8495 (17) Å | 0.56 × 0.35 × 0.24 mm |
β = 100.414 (1)° |
CCD area-detector diffractometer | 10146 independent reflections |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | 8569 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.988 | Rint = 0.027 |
40342 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.34 e Å−3 |
10146 reflections | Δρmin = −0.29 e Å−3 |
477 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 | ||
O1A | 0.70296 (4) | 0.41530 (11) | 0.25313 (3) | 0.02419 (17) | |
O2A | 0.70709 (4) | 0.51375 (11) | 0.35211 (3) | 0.02445 (17) | |
O3A | 0.35878 (4) | 0.45882 (11) | 0.07001 (3) | 0.02442 (17) | |
O4A | 0.07684 (4) | 0.86400 (10) | 0.20454 (3) | 0.02421 (17) | |
O5A | −0.02272 (4) | 0.63640 (10) | 0.18184 (3) | 0.02352 (16) | |
O1B | 0.96885 (4) | 0.17449 (11) | 0.03878 (3) | 0.02650 (17) | |
O2B | 0.93567 (4) | 0.07348 (11) | 0.13096 (3) | 0.02318 (16) | |
O3B | 0.55536 (4) | 0.26262 (11) | 0.10438 (3) | 0.02574 (17) | |
O4B | 0.22391 (4) | 0.28208 (11) | −0.09563 (3) | 0.02277 (16) | |
O5B | 0.23280 (4) | 0.19771 (11) | −0.19409 (3) | 0.02292 (16) | |
C1A | 0.51544 (5) | 0.55102 (12) | 0.24296 (4) | 0.01736 (18) | |
C2A | 0.57740 (5) | 0.48719 (13) | 0.22675 (4) | 0.01750 (18) | |
H2AA | 0.5761 | 0.4518 | 0.1900 | 0.021* | |
C3A | 0.63995 (5) | 0.47606 (13) | 0.26423 (4) | 0.01795 (19) | |
C4A | 0.64228 (5) | 0.52836 (13) | 0.31906 (4) | 0.01887 (19) | |
C5A | 0.58134 (6) | 0.58896 (13) | 0.33525 (4) | 0.0203 (2) | |
H5AA | 0.5824 | 0.6228 | 0.3721 | 0.024* | |
C6A | 0.51839 (5) | 0.60011 (13) | 0.29714 (4) | 0.01938 (19) | |
H6AA | 0.4767 | 0.6420 | 0.3084 | 0.023* | |
C7A | 0.70226 (6) | 0.35031 (15) | 0.19927 (4) | 0.0241 (2) | |
H7AA | 0.7499 | 0.3101 | 0.1962 | 0.036* | |
H7AB | 0.6877 | 0.4422 | 0.1725 | 0.036* | |
H7AC | 0.6687 | 0.2540 | 0.1921 | 0.036* | |
C8A | 0.70952 (7) | 0.54299 (16) | 0.40909 (5) | 0.0300 (3) | |
H8AA | 0.7580 | 0.5249 | 0.4289 | 0.045* | |
H8AB | 0.6774 | 0.4624 | 0.4228 | 0.045* | |
H8AC | 0.6948 | 0.6618 | 0.4148 | 0.045* | |
C9A | 0.44789 (5) | 0.56426 (13) | 0.20514 (4) | 0.01823 (19) | |
H9AA | 0.4086 | 0.6059 | 0.2198 | 0.022* | |
C10A | 0.43560 (5) | 0.52354 (13) | 0.15173 (4) | 0.01880 (19) | |
H10A | 0.4753 | 0.4958 | 0.1354 | 0.023* | |
C11A | 0.36532 (5) | 0.51882 (13) | 0.11681 (4) | 0.01848 (19) | |
C12A | 0.30154 (5) | 0.57637 (13) | 0.13791 (4) | 0.01858 (19) | |
H12A | 0.3056 | 0.6593 | 0.1665 | 0.022* | |
C13A | 0.23810 (5) | 0.50987 (13) | 0.11618 (4) | 0.01900 (19) | |
H13A | 0.2375 | 0.4299 | 0.0871 | 0.023* | |
C14A | 0.16988 (5) | 0.54584 (13) | 0.13193 (4) | 0.01782 (19) | |
C15A | 0.15812 (5) | 0.69605 (13) | 0.16107 (4) | 0.01781 (19) | |
H15A | 0.1948 | 0.7794 | 0.1698 | 0.021* | |
C16A | 0.09345 (5) | 0.72227 (13) | 0.17689 (4) | 0.01791 (19) | |
C17A | 0.03876 (5) | 0.59741 (13) | 0.16468 (4) | 0.01875 (19) | |
C18A | 0.05038 (5) | 0.44979 (14) | 0.13599 (4) | 0.0204 (2) | |
H18A | 0.0143 | 0.3649 | 0.1279 | 0.024* | |
C19A | 0.11532 (5) | 0.42641 (14) | 0.11907 (4) | 0.0204 (2) | |
H19A | 0.1224 | 0.3269 | 0.0984 | 0.025* | |
C20A | 0.11770 (6) | 1.01596 (15) | 0.20083 (6) | 0.0313 (3) | |
H20A | 0.0951 | 1.1144 | 0.2156 | 0.047* | |
H20B | 0.1204 | 1.0380 | 0.1624 | 0.047* | |
H20C | 0.1656 | 0.9999 | 0.2219 | 0.047* | |
C21A | −0.08162 (6) | 0.52357 (15) | 0.16435 (5) | 0.0269 (2) | |
H21A | −0.1246 | 0.5741 | 0.1739 | 0.040* | |
H21B | −0.0723 | 0.4115 | 0.1825 | 0.040* | |
H21C | −0.0882 | 0.5079 | 0.1246 | 0.040* | |
C1B | 0.75664 (5) | 0.19846 (13) | 0.05722 (4) | 0.01803 (19) | |
C2B | 0.77562 (6) | 0.25613 (14) | 0.00882 (4) | 0.0209 (2) | |
H2BA | 0.7403 | 0.3014 | −0.0194 | 0.025* | |
C3B | 0.84584 (6) | 0.24834 (14) | 0.00126 (4) | 0.0225 (2) | |
H3BA | 0.8577 | 0.2864 | −0.0323 | 0.027* | |
C4B | 0.89870 (5) | 0.18555 (14) | 0.04228 (4) | 0.0205 (2) | |
C5B | 0.88064 (5) | 0.12898 (13) | 0.09200 (4) | 0.01874 (19) | |
C6B | 0.81052 (5) | 0.13416 (13) | 0.09856 (4) | 0.01809 (19) | |
H6BA | 0.7984 | 0.0934 | 0.1317 | 0.022* | |
C7B | 0.98831 (7) | 0.22779 (19) | −0.01151 (5) | 0.0341 (3) | |
H7BA | 1.0395 | 0.2129 | −0.0093 | 0.051* | |
H7BB | 0.9759 | 0.3496 | −0.0182 | 0.051* | |
H7BC | 0.9629 | 0.1575 | −0.0416 | 0.051* | |
C8B | 0.91785 (6) | 0.02067 (15) | 0.18211 (4) | 0.0234 (2) | |
H8BA | 0.9608 | −0.0180 | 0.2068 | 0.035* | |
H8BB | 0.8836 | −0.0743 | 0.1758 | 0.035* | |
H8BC | 0.8970 | 0.1182 | 0.1987 | 0.035* | |
C9B | 0.68407 (5) | 0.20273 (13) | 0.06781 (4) | 0.01842 (19) | |
H9BA | 0.6772 | 0.1543 | 0.1016 | 0.022* | |
C10B | 0.62599 (5) | 0.26665 (14) | 0.03565 (4) | 0.01972 (19) | |
H10B | 0.6289 | 0.3116 | 0.0006 | 0.024* | |
C11B | 0.55731 (5) | 0.26688 (13) | 0.05515 (4) | 0.01883 (19) | |
C12B | 0.49040 (5) | 0.27168 (14) | 0.01548 (4) | 0.0203 (2) | |
H12B | 0.4485 | 0.3035 | 0.0285 | 0.024* | |
C13B | 0.48442 (5) | 0.23422 (13) | −0.03785 (4) | 0.0198 (2) | |
H13B | 0.5272 | 0.2112 | −0.0507 | 0.024* | |
C14B | 0.41874 (5) | 0.22514 (13) | −0.07822 (4) | 0.01829 (19) | |
C15B | 0.35178 (5) | 0.26085 (13) | −0.06460 (4) | 0.01829 (19) | |
H15B | 0.3484 | 0.2924 | −0.0282 | 0.022* | |
C16B | 0.29111 (5) | 0.24990 (13) | −0.10418 (4) | 0.01745 (19) | |
C17B | 0.29605 (5) | 0.20299 (13) | −0.15844 (4) | 0.01816 (19) | |
C18B | 0.36156 (6) | 0.16712 (13) | −0.17167 (4) | 0.0200 (2) | |
H18B | 0.3650 | 0.1348 | −0.2080 | 0.024* | |
C19B | 0.42248 (5) | 0.17860 (14) | −0.13161 (4) | 0.0205 (2) | |
H19B | 0.4674 | 0.1542 | −0.1410 | 0.025* | |
C20B | 0.21431 (6) | 0.28988 (17) | −0.04009 (5) | 0.0278 (2) | |
H20D | 0.1639 | 0.3061 | −0.0390 | 0.042* | |
H20E | 0.2416 | 0.3868 | −0.0217 | 0.042* | |
H20F | 0.2309 | 0.1820 | −0.0215 | 0.042* | |
C21B | 0.23441 (6) | 0.13995 (15) | −0.24840 (4) | 0.0253 (2) | |
H21D | 0.1859 | 0.1326 | −0.2691 | 0.038* | |
H21E | 0.2567 | 0.0259 | −0.2470 | 0.038* | |
H21F | 0.2617 | 0.2217 | −0.2664 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0163 (3) | 0.0342 (4) | 0.0214 (4) | 0.0047 (3) | 0.0016 (3) | −0.0053 (3) |
O2A | 0.0222 (4) | 0.0294 (4) | 0.0191 (4) | 0.0030 (3) | −0.0033 (3) | −0.0023 (3) |
O3A | 0.0203 (4) | 0.0366 (4) | 0.0169 (3) | 0.0041 (3) | 0.0046 (3) | −0.0010 (3) |
O4A | 0.0183 (3) | 0.0207 (4) | 0.0351 (4) | −0.0012 (3) | 0.0089 (3) | −0.0060 (3) |
O5A | 0.0137 (3) | 0.0242 (4) | 0.0338 (4) | −0.0017 (3) | 0.0073 (3) | −0.0027 (3) |
O1B | 0.0181 (4) | 0.0362 (4) | 0.0271 (4) | −0.0012 (3) | 0.0092 (3) | −0.0004 (3) |
O2B | 0.0148 (3) | 0.0317 (4) | 0.0227 (4) | 0.0029 (3) | 0.0026 (3) | 0.0037 (3) |
O3B | 0.0219 (4) | 0.0383 (4) | 0.0172 (4) | 0.0051 (3) | 0.0040 (3) | 0.0003 (3) |
O4B | 0.0158 (3) | 0.0340 (4) | 0.0187 (3) | 0.0047 (3) | 0.0037 (3) | −0.0016 (3) |
O5B | 0.0203 (4) | 0.0321 (4) | 0.0153 (3) | −0.0008 (3) | 0.0004 (3) | −0.0028 (3) |
C1A | 0.0166 (4) | 0.0167 (4) | 0.0188 (4) | 0.0001 (3) | 0.0034 (3) | 0.0011 (3) |
C2A | 0.0176 (4) | 0.0192 (4) | 0.0158 (4) | 0.0001 (3) | 0.0033 (3) | 0.0003 (3) |
C3A | 0.0162 (4) | 0.0181 (4) | 0.0197 (5) | 0.0012 (3) | 0.0037 (4) | 0.0006 (4) |
C4A | 0.0201 (5) | 0.0173 (4) | 0.0178 (4) | −0.0005 (4) | 0.0000 (4) | 0.0013 (3) |
C5A | 0.0247 (5) | 0.0192 (4) | 0.0170 (4) | −0.0006 (4) | 0.0041 (4) | −0.0011 (4) |
C6A | 0.0203 (5) | 0.0191 (4) | 0.0199 (5) | 0.0007 (4) | 0.0067 (4) | 0.0000 (4) |
C7A | 0.0212 (5) | 0.0289 (5) | 0.0229 (5) | 0.0041 (4) | 0.0054 (4) | −0.0039 (4) |
C8A | 0.0350 (6) | 0.0329 (6) | 0.0187 (5) | 0.0019 (5) | −0.0041 (4) | −0.0009 (4) |
C9A | 0.0158 (4) | 0.0179 (4) | 0.0215 (5) | 0.0017 (3) | 0.0049 (4) | 0.0013 (4) |
C10A | 0.0145 (4) | 0.0220 (5) | 0.0204 (5) | 0.0029 (4) | 0.0046 (4) | 0.0011 (4) |
C11A | 0.0170 (4) | 0.0207 (4) | 0.0184 (4) | 0.0022 (4) | 0.0050 (4) | 0.0032 (4) |
C12A | 0.0172 (4) | 0.0218 (5) | 0.0173 (4) | 0.0036 (4) | 0.0045 (4) | 0.0013 (4) |
C13A | 0.0181 (4) | 0.0230 (5) | 0.0164 (4) | 0.0027 (4) | 0.0044 (3) | 0.0009 (4) |
C14A | 0.0152 (4) | 0.0227 (5) | 0.0156 (4) | 0.0019 (4) | 0.0027 (3) | 0.0027 (4) |
C15A | 0.0142 (4) | 0.0202 (4) | 0.0187 (4) | −0.0003 (3) | 0.0021 (3) | 0.0016 (4) |
C16A | 0.0158 (4) | 0.0189 (4) | 0.0188 (4) | 0.0010 (3) | 0.0027 (3) | 0.0005 (3) |
C17A | 0.0134 (4) | 0.0223 (5) | 0.0209 (5) | 0.0006 (3) | 0.0038 (3) | 0.0030 (4) |
C18A | 0.0167 (4) | 0.0216 (5) | 0.0222 (5) | −0.0025 (4) | 0.0018 (4) | −0.0001 (4) |
C19A | 0.0190 (5) | 0.0223 (5) | 0.0195 (5) | 0.0005 (4) | 0.0024 (4) | −0.0021 (4) |
C20A | 0.0262 (5) | 0.0203 (5) | 0.0491 (7) | −0.0033 (4) | 0.0111 (5) | −0.0044 (5) |
C21A | 0.0152 (4) | 0.0283 (5) | 0.0373 (6) | −0.0037 (4) | 0.0050 (4) | −0.0003 (5) |
C1B | 0.0166 (4) | 0.0194 (4) | 0.0179 (4) | 0.0002 (3) | 0.0026 (3) | −0.0019 (3) |
C2B | 0.0197 (5) | 0.0249 (5) | 0.0176 (5) | −0.0002 (4) | 0.0018 (4) | 0.0001 (4) |
C3B | 0.0234 (5) | 0.0272 (5) | 0.0181 (5) | −0.0021 (4) | 0.0065 (4) | −0.0006 (4) |
C4B | 0.0170 (4) | 0.0227 (5) | 0.0225 (5) | −0.0022 (4) | 0.0058 (4) | −0.0042 (4) |
C5B | 0.0167 (4) | 0.0192 (4) | 0.0197 (5) | 0.0008 (3) | 0.0018 (4) | −0.0015 (4) |
C6B | 0.0175 (4) | 0.0197 (4) | 0.0171 (4) | 0.0009 (3) | 0.0032 (3) | −0.0006 (3) |
C7B | 0.0270 (6) | 0.0455 (7) | 0.0339 (7) | −0.0015 (5) | 0.0167 (5) | 0.0033 (5) |
C8B | 0.0185 (5) | 0.0284 (5) | 0.0230 (5) | 0.0034 (4) | 0.0031 (4) | 0.0049 (4) |
C9B | 0.0182 (4) | 0.0204 (4) | 0.0169 (4) | 0.0007 (4) | 0.0039 (4) | −0.0006 (4) |
C10B | 0.0179 (4) | 0.0239 (5) | 0.0174 (4) | 0.0002 (4) | 0.0033 (4) | 0.0013 (4) |
C11B | 0.0174 (4) | 0.0207 (4) | 0.0183 (5) | 0.0025 (4) | 0.0029 (4) | 0.0002 (4) |
C12B | 0.0157 (4) | 0.0249 (5) | 0.0206 (5) | 0.0030 (4) | 0.0035 (4) | 0.0003 (4) |
C13B | 0.0156 (4) | 0.0229 (5) | 0.0214 (5) | 0.0016 (4) | 0.0048 (4) | −0.0006 (4) |
C14B | 0.0170 (4) | 0.0194 (4) | 0.0186 (5) | 0.0004 (3) | 0.0034 (4) | −0.0007 (4) |
C15B | 0.0180 (4) | 0.0214 (5) | 0.0155 (4) | 0.0018 (4) | 0.0031 (4) | −0.0009 (3) |
C16B | 0.0166 (4) | 0.0186 (4) | 0.0175 (4) | 0.0018 (3) | 0.0043 (4) | 0.0002 (3) |
C17B | 0.0191 (4) | 0.0186 (4) | 0.0161 (4) | −0.0013 (4) | 0.0015 (4) | 0.0005 (3) |
C18B | 0.0233 (5) | 0.0213 (5) | 0.0164 (4) | −0.0014 (4) | 0.0059 (4) | −0.0017 (4) |
C19B | 0.0181 (4) | 0.0239 (5) | 0.0207 (5) | −0.0003 (4) | 0.0067 (4) | −0.0021 (4) |
C20B | 0.0225 (5) | 0.0411 (6) | 0.0212 (5) | 0.0049 (5) | 0.0075 (4) | −0.0036 (5) |
C21B | 0.0302 (6) | 0.0287 (5) | 0.0156 (5) | −0.0008 (4) | 0.0005 (4) | −0.0035 (4) |
O1A—C3A | 1.3698 (12) | C18A—C19A | 1.3956 (15) |
O1A—C7A | 1.4277 (13) | C18A—H18A | 0.9500 |
O2A—C4A | 1.3642 (12) | C19A—H19A | 0.9500 |
O2A—C8A | 1.4265 (14) | C20A—H20A | 0.9800 |
O3A—C11A | 1.2375 (13) | C20A—H20B | 0.9800 |
O4A—C16A | 1.3633 (12) | C20A—H20C | 0.9800 |
O4A—C20A | 1.4262 (13) | C21A—H21A | 0.9800 |
O5A—C17A | 1.3574 (12) | C21A—H21B | 0.9800 |
O5A—C21A | 1.4319 (13) | C21A—H21C | 0.9800 |
O1B—C4B | 1.3654 (12) | C1B—C2B | 1.3917 (15) |
O1B—C7B | 1.4280 (14) | C1B—C6B | 1.4092 (13) |
O2B—C5B | 1.3657 (12) | C1B—C9B | 1.4619 (14) |
O2B—C8B | 1.4342 (13) | C2B—C3B | 1.3933 (15) |
O3B—C11B | 1.2310 (13) | C2B—H2BA | 0.9500 |
O4B—C16B | 1.3655 (12) | C3B—C4B | 1.3890 (15) |
O4B—C20B | 1.4261 (13) | C3B—H3BA | 0.9500 |
O5B—C17B | 1.3667 (12) | C4B—C5B | 1.4117 (15) |
O5B—C21B | 1.4273 (13) | C5B—C6B | 1.3833 (14) |
C1A—C6A | 1.3903 (14) | C6B—H6BA | 0.9500 |
C1A—C2A | 1.4105 (14) | C7B—H7BA | 0.9800 |
C1A—C9A | 1.4594 (13) | C7B—H7BB | 0.9800 |
C2A—C3A | 1.3815 (13) | C7B—H7BC | 0.9800 |
C2A—H2AA | 0.9500 | C8B—H8BA | 0.9800 |
C3A—C4A | 1.4142 (14) | C8B—H8BB | 0.9800 |
C4A—C5A | 1.3843 (15) | C8B—H8BC | 0.9800 |
C5A—C6A | 1.3952 (14) | C9B—C10B | 1.3420 (14) |
C5A—H5AA | 0.9500 | C9B—H9BA | 0.9500 |
C6A—H6AA | 0.9500 | C10B—C11B | 1.4824 (14) |
C7A—H7AA | 0.9800 | C10B—H10B | 0.9500 |
C7A—H7AB | 0.9800 | C11B—C12B | 1.4699 (14) |
C7A—H7AC | 0.9800 | C12B—C13B | 1.3411 (15) |
C8A—H8AA | 0.9800 | C12B—H12B | 0.9500 |
C8A—H8AB | 0.9800 | C13B—C14B | 1.4626 (14) |
C8A—H8AC | 0.9800 | C13B—H13B | 0.9500 |
C9A—C10A | 1.3429 (14) | C14B—C19B | 1.3893 (14) |
C9A—H9AA | 0.9500 | C14B—C15B | 1.4123 (14) |
C10A—C11A | 1.4649 (13) | C15B—C16B | 1.3833 (13) |
C10A—H10A | 0.9500 | C15B—H15B | 0.9500 |
C11A—C12A | 1.4832 (14) | C16B—C17B | 1.4159 (14) |
C12A—C13A | 1.3409 (14) | C17B—C18B | 1.3824 (14) |
C12A—H12A | 0.9500 | C18B—C19B | 1.3935 (14) |
C13A—C14A | 1.4578 (14) | C18B—H18B | 0.9500 |
C13A—H13A | 0.9500 | C19B—H19B | 0.9500 |
C14A—C19A | 1.3897 (14) | C20B—H20D | 0.9800 |
C14A—C15A | 1.4102 (14) | C20B—H20E | 0.9800 |
C15A—C16A | 1.3813 (14) | C20B—H20F | 0.9800 |
C15A—H15A | 0.9500 | C21B—H21D | 0.9800 |
C16A—C17A | 1.4184 (14) | C21B—H21E | 0.9800 |
C17A—C18A | 1.3870 (15) | C21B—H21F | 0.9800 |
C3A—O1A—C7A | 116.80 (8) | H21A—C21A—H21B | 109.5 |
C4A—O2A—C8A | 116.57 (9) | O5A—C21A—H21C | 109.5 |
C16A—O4A—C20A | 116.84 (9) | H21A—C21A—H21C | 109.5 |
C17A—O5A—C21A | 116.75 (9) | H21B—C21A—H21C | 109.5 |
C4B—O1B—C7B | 116.98 (9) | C2B—C1B—C6B | 118.16 (9) |
C5B—O2B—C8B | 116.16 (8) | C2B—C1B—C9B | 123.64 (9) |
C16B—O4B—C20B | 116.66 (8) | C6B—C1B—C9B | 118.19 (9) |
C17B—O5B—C21B | 117.00 (8) | C1B—C2B—C3B | 120.82 (10) |
C6A—C1A—C2A | 118.92 (9) | C1B—C2B—H2BA | 119.6 |
C6A—C1A—C9A | 118.71 (9) | C3B—C2B—H2BA | 119.6 |
C2A—C1A—C9A | 122.37 (9) | C4B—C3B—C2B | 120.69 (10) |
C3A—C2A—C1A | 120.14 (9) | C4B—C3B—H3BA | 119.7 |
C3A—C2A—H2AA | 119.9 | C2B—C3B—H3BA | 119.7 |
C1A—C2A—H2AA | 119.9 | O1B—C4B—C3B | 124.82 (10) |
O1A—C3A—C2A | 125.08 (9) | O1B—C4B—C5B | 115.87 (9) |
O1A—C3A—C4A | 114.65 (8) | C3B—C4B—C5B | 119.30 (9) |
C2A—C3A—C4A | 120.27 (9) | O2B—C5B—C6B | 124.61 (9) |
O2A—C4A—C5A | 125.26 (9) | O2B—C5B—C4B | 115.98 (9) |
O2A—C4A—C3A | 115.02 (9) | C6B—C5B—C4B | 119.42 (9) |
C5A—C4A—C3A | 119.71 (9) | C5B—C6B—C1B | 121.59 (10) |
C4A—C5A—C6A | 119.69 (9) | C5B—C6B—H6BA | 119.2 |
C4A—C5A—H5AA | 120.2 | C1B—C6B—H6BA | 119.2 |
C6A—C5A—H5AA | 120.2 | O1B—C7B—H7BA | 109.5 |
C1A—C6A—C5A | 121.27 (9) | O1B—C7B—H7BB | 109.5 |
C1A—C6A—H6AA | 119.4 | H7BA—C7B—H7BB | 109.5 |
C5A—C6A—H6AA | 119.4 | O1B—C7B—H7BC | 109.5 |
O1A—C7A—H7AA | 109.5 | H7BA—C7B—H7BC | 109.5 |
O1A—C7A—H7AB | 109.5 | H7BB—C7B—H7BC | 109.5 |
H7AA—C7A—H7AB | 109.5 | O2B—C8B—H8BA | 109.5 |
O1A—C7A—H7AC | 109.5 | O2B—C8B—H8BB | 109.5 |
H7AA—C7A—H7AC | 109.5 | H8BA—C8B—H8BB | 109.5 |
H7AB—C7A—H7AC | 109.5 | O2B—C8B—H8BC | 109.5 |
O2A—C8A—H8AA | 109.5 | H8BA—C8B—H8BC | 109.5 |
O2A—C8A—H8AB | 109.5 | H8BB—C8B—H8BC | 109.5 |
H8AA—C8A—H8AB | 109.5 | C10B—C9B—C1B | 127.94 (10) |
O2A—C8A—H8AC | 109.5 | C10B—C9B—H9BA | 116.0 |
H8AA—C8A—H8AC | 109.5 | C1B—C9B—H9BA | 116.0 |
H8AB—C8A—H8AC | 109.5 | C9B—C10B—C11B | 119.72 (9) |
C10A—C9A—C1A | 126.63 (9) | C9B—C10B—H10B | 120.1 |
C10A—C9A—H9AA | 116.7 | C11B—C10B—H10B | 120.1 |
C1A—C9A—H9AA | 116.7 | O3B—C11B—C12B | 119.19 (9) |
C9A—C10A—C11A | 124.72 (9) | O3B—C11B—C10B | 120.86 (9) |
C9A—C10A—H10A | 117.6 | C12B—C11B—C10B | 119.96 (9) |
C11A—C10A—H10A | 117.6 | C13B—C12B—C11B | 124.44 (9) |
O3A—C11A—C10A | 119.48 (9) | C13B—C12B—H12B | 117.8 |
O3A—C11A—C12A | 119.69 (9) | C11B—C12B—H12B | 117.8 |
C10A—C11A—C12A | 120.75 (9) | C12B—C13B—C14B | 126.68 (10) |
C13A—C12A—C11A | 119.16 (9) | C12B—C13B—H13B | 116.7 |
C13A—C12A—H12A | 120.4 | C14B—C13B—H13B | 116.7 |
C11A—C12A—H12A | 120.4 | C19B—C14B—C15B | 119.05 (9) |
C12A—C13A—C14A | 127.61 (10) | C19B—C14B—C13B | 118.75 (9) |
C12A—C13A—H13A | 116.2 | C15B—C14B—C13B | 122.20 (9) |
C14A—C13A—H13A | 116.2 | C16B—C15B—C14B | 120.08 (9) |
C19A—C14A—C15A | 118.97 (9) | C16B—C15B—H15B | 120.0 |
C19A—C14A—C13A | 119.01 (9) | C14B—C15B—H15B | 120.0 |
C15A—C14A—C13A | 122.00 (9) | O4B—C16B—C15B | 124.98 (9) |
C16A—C15A—C14A | 120.15 (9) | O4B—C16B—C17B | 114.99 (8) |
C16A—C15A—H15A | 119.9 | C15B—C16B—C17B | 120.03 (9) |
C14A—C15A—H15A | 119.9 | O5B—C17B—C18B | 125.24 (9) |
O4A—C16A—C15A | 124.41 (9) | O5B—C17B—C16B | 114.89 (9) |
O4A—C16A—C17A | 115.24 (9) | C18B—C17B—C16B | 119.88 (9) |
C15A—C16A—C17A | 120.35 (9) | C17B—C18B—C19B | 119.79 (9) |
O5A—C17A—C18A | 125.04 (9) | C17B—C18B—H18B | 120.1 |
O5A—C17A—C16A | 115.52 (9) | C19B—C18B—H18B | 120.1 |
C18A—C17A—C16A | 119.43 (9) | C14B—C19B—C18B | 121.17 (9) |
C17A—C18A—C19A | 119.79 (9) | C14B—C19B—H19B | 119.4 |
C17A—C18A—H18A | 120.1 | C18B—C19B—H19B | 119.4 |
C19A—C18A—H18A | 120.1 | O4B—C20B—H20D | 109.5 |
C14A—C19A—C18A | 121.27 (10) | O4B—C20B—H20E | 109.5 |
C14A—C19A—H19A | 119.4 | H20D—C20B—H20E | 109.5 |
C18A—C19A—H19A | 119.4 | O4B—C20B—H20F | 109.5 |
O4A—C20A—H20A | 109.5 | H20D—C20B—H20F | 109.5 |
O4A—C20A—H20B | 109.5 | H20E—C20B—H20F | 109.5 |
H20A—C20A—H20B | 109.5 | O5B—C21B—H21D | 109.5 |
O4A—C20A—H20C | 109.5 | O5B—C21B—H21E | 109.5 |
H20A—C20A—H20C | 109.5 | H21D—C21B—H21E | 109.5 |
H20B—C20A—H20C | 109.5 | O5B—C21B—H21F | 109.5 |
O5A—C21A—H21A | 109.5 | H21D—C21B—H21F | 109.5 |
O5A—C21A—H21B | 109.5 | H21E—C21B—H21F | 109.5 |
C6A—C1A—C2A—C3A | −0.78 (14) | C6B—C1B—C2B—C3B | 0.80 (15) |
C9A—C1A—C2A—C3A | −179.53 (9) | C9B—C1B—C2B—C3B | −179.93 (10) |
C7A—O1A—C3A—C2A | −3.51 (15) | C1B—C2B—C3B—C4B | −1.13 (16) |
C7A—O1A—C3A—C4A | 176.01 (9) | C7B—O1B—C4B—C3B | −1.64 (16) |
C1A—C2A—C3A—O1A | 179.57 (9) | C7B—O1B—C4B—C5B | 178.82 (10) |
C1A—C2A—C3A—C4A | 0.06 (15) | C2B—C3B—C4B—O1B | −179.40 (10) |
C8A—O2A—C4A—C5A | 8.28 (15) | C2B—C3B—C4B—C5B | 0.12 (16) |
C8A—O2A—C4A—C3A | −171.83 (9) | C8B—O2B—C5B—C6B | −1.15 (15) |
O1A—C3A—C4A—O2A | 1.32 (13) | C8B—O2B—C5B—C4B | 178.23 (9) |
C2A—C3A—C4A—O2A | −179.13 (9) | O1B—C4B—C5B—O2B | 1.32 (14) |
O1A—C3A—C4A—C5A | −178.78 (9) | C3B—C4B—C5B—O2B | −178.24 (9) |
C2A—C3A—C4A—C5A | 0.77 (15) | O1B—C4B—C5B—C6B | −179.26 (9) |
O2A—C4A—C5A—C6A | 179.01 (9) | C3B—C4B—C5B—C6B | 1.18 (15) |
C3A—C4A—C5A—C6A | −0.88 (15) | O2B—C5B—C6B—C1B | 177.85 (9) |
C2A—C1A—C6A—C5A | 0.67 (15) | C4B—C5B—C6B—C1B | −1.51 (15) |
C9A—C1A—C6A—C5A | 179.47 (9) | C2B—C1B—C6B—C5B | 0.52 (15) |
C4A—C5A—C6A—C1A | 0.16 (15) | C9B—C1B—C6B—C5B | −178.78 (9) |
C6A—C1A—C9A—C10A | 179.67 (10) | C2B—C1B—C9B—C10B | −3.14 (17) |
C2A—C1A—C9A—C10A | −1.58 (16) | C6B—C1B—C9B—C10B | 176.12 (10) |
C1A—C9A—C10A—C11A | 172.18 (9) | C1B—C9B—C10B—C11B | −176.83 (9) |
C9A—C10A—C11A—O3A | −170.90 (10) | C9B—C10B—C11B—O3B | 23.27 (15) |
C9A—C10A—C11A—C12A | 5.81 (16) | C9B—C10B—C11B—C12B | −156.53 (10) |
O3A—C11A—C12A—C13A | 23.71 (15) | O3B—C11B—C12B—C13B | −162.80 (11) |
C10A—C11A—C12A—C13A | −153.00 (10) | C10B—C11B—C12B—C13B | 17.01 (16) |
C11A—C12A—C13A—C14A | 178.36 (9) | C11B—C12B—C13B—C14B | 175.38 (10) |
C12A—C13A—C14A—C19A | −158.01 (11) | C12B—C13B—C14B—C19B | −177.88 (11) |
C12A—C13A—C14A—C15A | 20.32 (16) | C12B—C13B—C14B—C15B | 1.64 (17) |
C19A—C14A—C15A—C16A | 0.62 (14) | C19B—C14B—C15B—C16B | −0.23 (15) |
C13A—C14A—C15A—C16A | −177.70 (9) | C13B—C14B—C15B—C16B | −179.76 (9) |
C20A—O4A—C16A—C15A | 21.79 (15) | C20B—O4B—C16B—C15B | −14.48 (15) |
C20A—O4A—C16A—C17A | −158.30 (10) | C20B—O4B—C16B—C17B | 165.79 (9) |
C14A—C15A—C16A—O4A | −179.19 (9) | C14B—C15B—C16B—O4B | −179.77 (9) |
C14A—C15A—C16A—C17A | 0.91 (15) | C14B—C15B—C16B—C17B | −0.05 (15) |
C21A—O5A—C17A—C18A | −6.10 (15) | C21B—O5B—C17B—C18B | 4.18 (15) |
C21A—O5A—C17A—C16A | 172.56 (9) | C21B—O5B—C17B—C16B | −175.94 (9) |
O4A—C16A—C17A—O5A | 0.40 (13) | O4B—C16B—C17B—O5B | 0.25 (13) |
C15A—C16A—C17A—O5A | −179.69 (9) | C15B—C16B—C17B—O5B | −179.49 (9) |
O4A—C16A—C17A—C18A | 179.14 (9) | O4B—C16B—C17B—C18B | −179.85 (9) |
C15A—C16A—C17A—C18A | −0.94 (15) | C15B—C16B—C17B—C18B | 0.41 (15) |
O5A—C17A—C18A—C19A | 178.06 (10) | O5B—C17B—C18B—C19B | 179.41 (10) |
C16A—C17A—C18A—C19A | −0.56 (15) | C16B—C17B—C18B—C19B | −0.48 (15) |
C15A—C14A—C19A—C18A | −2.16 (15) | C15B—C14B—C19B—C18B | 0.16 (16) |
C13A—C14A—C19A—C18A | 176.22 (9) | C13B—C14B—C19B—C18B | 179.70 (9) |
C17A—C18A—C19A—C14A | 2.13 (16) | C17B—C18B—C19B—C14B | 0.20 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O3Bi | 0.95 | 2.54 | 3.2898 (13) | 137 |
C8A—H8AC···O3Ai | 0.98 | 2.58 | 3.5513 (15) | 173 |
C20A—H20C···O1Ai | 0.98 | 2.57 | 3.5085 (15) | 161 |
C8B—H8BA···O4Aii | 0.98 | 2.41 | 3.2334 (13) | 141 |
C8B—H8BB···O5Biii | 0.98 | 2.54 | 3.4056 (14) | 147 |
C10B—H10B···O3Aiv | 0.95 | 2.54 | 3.4325 (13) | 157 |
C12B—H12B···O3A | 0.95 | 2.47 | 3.3968 (13) | 164 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H22O5 |
Mr | 354.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 103 |
a, b, c (Å) | 19.1646 (13), 7.7488 (5), 24.8495 (17) |
β (°) | 100.414 (1) |
V (Å3) | 3629.4 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.56 × 0.35 × 0.24 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.950, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40342, 10146, 8569 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.697 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.114, 1.03 |
No. of reflections | 10146 |
No. of parameters | 477 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.29 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O3Bi | 0.95 | 2.54 | 3.2898 (13) | 136.5 |
C8A—H8AC···O3Ai | 0.98 | 2.58 | 3.5513 (15) | 173.1 |
C20A—H20C···O1Ai | 0.98 | 2.57 | 3.5085 (15) | 161.0 |
C8B—H8BA···O4Aii | 0.98 | 2.41 | 3.2334 (13) | 140.8 |
C8B—H8BB···O5Biii | 0.98 | 2.54 | 3.4056 (14) | 147.0 |
C10B—H10B···O3Aiv | 0.95 | 2.54 | 3.4325 (13) | 156.8 |
C12B—H12B···O3A | 0.95 | 2.47 | 3.3968 (13) | 164.2 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z. |
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The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related 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 at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.