Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027559/wn2146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027559/wn2146Isup2.hkl |
CCDC reference: 654958
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.110
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. O3 .. 3.05 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
0 ALERT level A = In general: serious problem 1 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Du, Bao et al. (2006); Du, Liu et al. (2006); Sardjiman et al. (1997); Youssef et al. (2004).
The title compound was synthesized as previously described (Du, Liu et al., 2006). A mixture of 3-bromo-4-hydroxy-5-methoxybenzaldehyde (0.01 mol) and cyclohexanone (0.005 mol) was dissolved in glacial acetic acid (10 ml) saturated with anhydrous hydrogen chloride and heated in a water bath at 25–30 °C for 2 h. After standing for 2 days, the mixture was treated with cold water and filtered to obtain a yellow solid. Crystals were obtained by recrystallization from acetic acid and water (1:1) The compound identity was confirmed by the 1H NMR spectra and ESI-MS. 1H NMR (DMSO-d6, 300 MHz) δ, 9.94 (br, 2H, –OH), 7.50 (s, 2H, –CH=), 7.27 (2H, aromatic), 7.13 (2H, aromatic), 3.86 (s, 6H, OCH3), 2.88 (t, J = 6.7 Hz, 4H, –CH2—C—CH2–), 1.73 (q, J = 6.7 Hz, 2H, –C—CH2—C–). ESI-MS (m/z):523[M]-.
All H atoms were positioned geometrically and refined in a riding model, with C—H = 0.98 Å for methyl, C—H = 0.99 Å for methylene, Csp2—H = 0.95 Å and O—H = 0.84 Å. Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for other C; Uiso(H) = 1.5Ueq(O).
Curcumin analogs exhibit potential antioxidative properties (Sardjiman et al., 1997, Youssef et al., 2004) and inhibitory activities on α-glucosidase (Du, Liu et al., 2006) and on aldose reductase (Du, Bao et al., 2006). The title compound, C22H20Br2O5, is a synthesized curcumin analog and we report here its crystal structure.
The X-ray crystallographic study of the title compound confirms the previously proposed molecular structure based on spectroscopic data (Fig. 1). The C—C, C═C, C—O and C═O distances show no remarkable features.
A structural feature is the presence of intermolecular O—H···O hydrogen bonds between the hydroxy groups and the methoxy groups O of neighboring molecules (Table 2), resulting in infinite chains along the c axis (Fig. 2). Furthermore, there is a short intermolecular contact between the carbonyl O atom and a Br atom; Br2···O3 = 3.051 (3) Å.
For related literature, see: Du, Bao et al. (2006); Du, Liu et al. (2006); Sardjiman et al. (1997); Youssef et al. (2004).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C22H20Br2O5 | F(000) = 1048 |
Mr = 524.20 | Dx = 1.744 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2576 reflections |
a = 7.5550 (11) Å | θ = 2.3–26.7° |
b = 14.938 (2) Å | µ = 4.09 mm−1 |
c = 17.763 (3) Å | T = 173 K |
β = 95.201 (3)° | Needle, colorless |
V = 1996.4 (5) Å3 | 0.32 × 0.12 × 0.10 mm |
Z = 4 |
Bruker SMART 1000 CCD area-detector diffractometer | 4349 independent reflections |
Radiation source: fine-focus sealed tube | 2760 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 27.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.354, Tmax = 0.685 | k = −19→11 |
10131 measured reflections | l = −21→22 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3 |
4349 reflections | (Δ/σ)max = 0.001 |
266 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
C22H20Br2O5 | V = 1996.4 (5) Å3 |
Mr = 524.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.5550 (11) Å | µ = 4.09 mm−1 |
b = 14.938 (2) Å | T = 173 K |
c = 17.763 (3) Å | 0.32 × 0.12 × 0.10 mm |
β = 95.201 (3)° |
Bruker SMART 1000 CCD area-detector diffractometer | 4349 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2760 reflections with I > 2σ(I) |
Tmin = 0.354, Tmax = 0.685 | Rint = 0.052 |
10131 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.78 e Å−3 |
4349 reflections | Δρmin = −0.54 e Å−3 |
266 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 | ||
Br1 | 0.34530 (7) | 0.66581 (3) | −0.31408 (3) | 0.03229 (16) | |
Br2 | 0.52599 (7) | 0.71802 (3) | 0.39084 (3) | 0.02742 (15) | |
C1 | 0.1939 (6) | 0.4930 (3) | −0.3194 (2) | 0.0212 (10) | |
C2 | 0.1366 (6) | 0.4134 (3) | −0.2891 (2) | 0.0223 (11) | |
C3 | 0.1561 (6) | 0.3987 (3) | −0.2116 (2) | 0.0213 (10) | |
H3 | 0.1203 | 0.3434 | −0.1915 | 0.026* | |
C4 | 0.2296 (6) | 0.4667 (3) | −0.1626 (2) | 0.0190 (10) | |
C5 | 0.2868 (6) | 0.5456 (3) | −0.1942 (2) | 0.0209 (10) | |
H5 | 0.3390 | 0.5915 | −0.1624 | 0.025* | |
C6 | 0.2681 (6) | 0.5576 (3) | −0.2718 (2) | 0.0196 (10) | |
C7 | 0.2418 (6) | 0.4468 (3) | −0.0817 (2) | 0.0203 (10) | |
H7 | 0.2416 | 0.3849 | −0.0695 | 0.024* | |
C8 | 0.2534 (6) | 0.5023 (3) | −0.0219 (2) | 0.0174 (10) | |
C9 | 0.2528 (6) | 0.4578 (3) | 0.0543 (2) | 0.0219 (10) | |
C10 | 0.2709 (6) | 0.5150 (3) | 0.1238 (2) | 0.0196 (10) | |
C11 | 0.2874 (6) | 0.6152 (3) | 0.1154 (2) | 0.0214 (10) | |
H11A | 0.4147 | 0.6314 | 0.1168 | 0.026* | |
H11B | 0.2375 | 0.6451 | 0.1585 | 0.026* | |
C12 | 0.1907 (6) | 0.6488 (3) | 0.0415 (2) | 0.0222 (11) | |
H12A | 0.0618 | 0.6367 | 0.0415 | 0.027* | |
H12B | 0.2070 | 0.7143 | 0.0375 | 0.027* | |
C13 | 0.2619 (6) | 0.6028 (3) | −0.0258 (2) | 0.0209 (10) | |
H13A | 0.1927 | 0.6232 | −0.0726 | 0.025* | |
H13B | 0.3870 | 0.6211 | −0.0287 | 0.025* | |
C14 | 0.2704 (6) | 0.4718 (3) | 0.1901 (2) | 0.0213 (10) | |
H14 | 0.2517 | 0.4090 | 0.1859 | 0.026* | |
C15 | 0.2938 (6) | 0.5054 (3) | 0.2679 (2) | 0.0189 (10) | |
C16 | 0.2337 (6) | 0.4519 (3) | 0.3252 (2) | 0.0214 (10) | |
H16 | 0.1781 | 0.3962 | 0.3123 | 0.026* | |
C17 | 0.2540 (6) | 0.4787 (3) | 0.4005 (2) | 0.0212 (10) | |
C18 | 0.3355 (6) | 0.5595 (3) | 0.4206 (2) | 0.0230 (11) | |
C19 | 0.4016 (6) | 0.6104 (3) | 0.3643 (2) | 0.0205 (10) | |
C20 | 0.3827 (6) | 0.5844 (3) | 0.2892 (2) | 0.0207 (10) | |
H20 | 0.4304 | 0.6206 | 0.2520 | 0.025* | |
C21 | 0.0191 (6) | 0.2687 (3) | −0.3221 (3) | 0.0253 (11) | |
H21A | 0.1239 | 0.2395 | −0.2965 | 0.038* | |
H21B | −0.0219 | 0.2347 | −0.3676 | 0.038* | |
H21C | −0.0757 | 0.2710 | −0.2880 | 0.038* | |
C22 | 0.1460 (7) | 0.3418 (3) | 0.4464 (3) | 0.0317 (13) | |
H22A | 0.0396 | 0.3405 | 0.4105 | 0.048* | |
H22B | 0.1194 | 0.3140 | 0.4940 | 0.048* | |
H22C | 0.2420 | 0.3086 | 0.4252 | 0.048* | |
O1 | 0.1786 (5) | 0.5049 (2) | −0.39617 (16) | 0.0311 (8) | |
H1 | 0.1417 | 0.4573 | −0.4174 | 0.047* | |
O2 | 0.0631 (5) | 0.3551 (2) | −0.34238 (17) | 0.0318 (8) | |
O3 | 0.2381 (5) | 0.3768 (2) | 0.05909 (16) | 0.0324 (9) | |
O4 | 0.1989 (5) | 0.4304 (2) | 0.45967 (17) | 0.0320 (8) | |
O5 | 0.3565 (5) | 0.5901 (2) | 0.49255 (16) | 0.0345 (9) | |
H5A | 0.3062 | 0.5550 | 0.5208 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0472 (4) | 0.0255 (3) | 0.0249 (3) | −0.0022 (2) | 0.0072 (2) | 0.0048 (2) |
Br2 | 0.0337 (3) | 0.0243 (3) | 0.0237 (3) | −0.0030 (2) | −0.0007 (2) | −0.0040 (2) |
C1 | 0.019 (2) | 0.030 (3) | 0.014 (2) | 0.008 (2) | 0.0015 (18) | 0.003 (2) |
C2 | 0.019 (3) | 0.026 (3) | 0.023 (2) | 0.002 (2) | 0.003 (2) | −0.008 (2) |
C3 | 0.020 (2) | 0.023 (3) | 0.021 (2) | 0.003 (2) | 0.0027 (19) | −0.004 (2) |
C4 | 0.016 (2) | 0.026 (3) | 0.015 (2) | 0.006 (2) | 0.0057 (18) | −0.0016 (19) |
C5 | 0.024 (3) | 0.026 (3) | 0.012 (2) | 0.003 (2) | 0.0013 (18) | −0.0012 (19) |
C6 | 0.024 (3) | 0.015 (2) | 0.021 (2) | 0.0020 (19) | 0.0035 (19) | 0.0045 (19) |
C7 | 0.022 (3) | 0.020 (2) | 0.019 (2) | 0.001 (2) | 0.0006 (19) | 0.003 (2) |
C8 | 0.017 (2) | 0.019 (2) | 0.016 (2) | 0.0032 (19) | 0.0024 (18) | 0.0001 (19) |
C9 | 0.026 (3) | 0.020 (3) | 0.019 (2) | 0.004 (2) | −0.002 (2) | 0.003 (2) |
C10 | 0.024 (3) | 0.019 (2) | 0.016 (2) | 0.001 (2) | −0.0020 (19) | −0.0012 (19) |
C11 | 0.030 (3) | 0.020 (2) | 0.014 (2) | 0.002 (2) | 0.0021 (19) | −0.0030 (19) |
C12 | 0.032 (3) | 0.013 (2) | 0.022 (2) | 0.004 (2) | −0.001 (2) | 0.0020 (19) |
C13 | 0.026 (3) | 0.020 (2) | 0.016 (2) | 0.000 (2) | −0.0001 (19) | 0.002 (2) |
C14 | 0.026 (3) | 0.019 (2) | 0.018 (2) | −0.001 (2) | 0.001 (2) | 0.0001 (19) |
C15 | 0.024 (3) | 0.020 (2) | 0.012 (2) | 0.004 (2) | 0.0005 (18) | 0.0012 (19) |
C16 | 0.023 (3) | 0.019 (2) | 0.023 (2) | 0.001 (2) | 0.002 (2) | −0.002 (2) |
C17 | 0.016 (2) | 0.026 (3) | 0.020 (2) | 0.002 (2) | −0.0009 (19) | 0.005 (2) |
C18 | 0.025 (3) | 0.031 (3) | 0.014 (2) | 0.006 (2) | 0.0031 (19) | 0.003 (2) |
C19 | 0.019 (2) | 0.023 (3) | 0.019 (2) | 0.005 (2) | −0.0009 (19) | −0.001 (2) |
C20 | 0.021 (3) | 0.025 (3) | 0.017 (2) | 0.001 (2) | 0.0029 (19) | 0.001 (2) |
C21 | 0.027 (3) | 0.017 (3) | 0.033 (3) | −0.009 (2) | 0.005 (2) | −0.014 (2) |
C22 | 0.045 (3) | 0.034 (3) | 0.015 (2) | −0.011 (3) | −0.003 (2) | 0.010 (2) |
O1 | 0.041 (2) | 0.036 (2) | 0.0162 (16) | 0.0011 (18) | 0.0039 (15) | −0.0011 (15) |
O2 | 0.043 (2) | 0.030 (2) | 0.0216 (17) | −0.0027 (16) | −0.0006 (16) | −0.0059 (15) |
O3 | 0.064 (3) | 0.0154 (18) | 0.0175 (16) | 0.0019 (17) | −0.0005 (16) | 0.0017 (14) |
O4 | 0.043 (2) | 0.034 (2) | 0.0186 (17) | −0.0100 (17) | 0.0035 (15) | 0.0032 (15) |
O5 | 0.053 (2) | 0.036 (2) | 0.0152 (17) | −0.0095 (18) | 0.0047 (16) | −0.0047 (15) |
Br1—C6 | 1.896 (4) | C12—H12B | 0.9900 |
Br2—C19 | 1.899 (5) | C13—H13A | 0.9900 |
C1—C6 | 1.369 (6) | C13—H13B | 0.9900 |
C1—O1 | 1.369 (5) | C14—C15 | 1.465 (6) |
C1—C2 | 1.390 (6) | C14—H14 | 0.9500 |
C2—O2 | 1.365 (5) | C15—C20 | 1.393 (6) |
C2—C3 | 1.390 (6) | C15—C16 | 1.401 (6) |
C3—C4 | 1.417 (6) | C16—C17 | 1.392 (6) |
C3—H3 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.391 (6) | C17—O4 | 1.370 (5) |
C4—C7 | 1.462 (6) | C17—C18 | 1.387 (6) |
C5—C6 | 1.385 (6) | C18—O5 | 1.353 (5) |
C5—H5 | 0.9500 | C18—C19 | 1.385 (6) |
C7—C8 | 1.344 (6) | C19—C20 | 1.385 (6) |
C7—H7 | 0.9500 | C20—H20 | 0.9500 |
C8—C13 | 1.505 (6) | C21—O2 | 1.388 (5) |
C8—C9 | 1.508 (6) | C21—H21A | 0.9800 |
C9—O3 | 1.219 (5) | C21—H21B | 0.9800 |
C9—C10 | 1.498 (6) | C21—H21C | 0.9800 |
C10—C14 | 1.343 (6) | C22—O4 | 1.397 (5) |
C10—C11 | 1.511 (6) | C22—H22A | 0.9800 |
C11—C12 | 1.527 (6) | C22—H22B | 0.9800 |
C11—H11A | 0.9900 | C22—H22C | 0.9800 |
C11—H11B | 0.9900 | O1—H1 | 0.8400 |
C12—C13 | 1.520 (6) | O5—H5A | 0.8400 |
C12—H12A | 0.9900 | ||
C6—C1—O1 | 121.1 (4) | C8—C13—H13A | 108.9 |
C6—C1—C2 | 119.2 (4) | C12—C13—H13A | 108.9 |
O1—C1—C2 | 119.6 (4) | C8—C13—H13B | 108.9 |
O2—C2—C3 | 125.9 (4) | C12—C13—H13B | 108.9 |
O2—C2—C1 | 113.5 (4) | H13A—C13—H13B | 107.7 |
C3—C2—C1 | 120.6 (4) | C10—C14—C15 | 130.8 (4) |
C2—C3—C4 | 119.8 (4) | C10—C14—H14 | 114.6 |
C2—C3—H3 | 120.1 | C15—C14—H14 | 114.6 |
C4—C3—H3 | 120.1 | C20—C15—C16 | 117.8 (4) |
C5—C4—C3 | 118.6 (4) | C20—C15—C14 | 124.1 (4) |
C5—C4—C7 | 125.1 (4) | C16—C15—C14 | 118.0 (4) |
C3—C4—C7 | 116.4 (4) | C17—C16—C15 | 121.3 (4) |
C6—C5—C4 | 120.3 (4) | C17—C16—H16 | 119.4 |
C6—C5—H5 | 119.9 | C15—C16—H16 | 119.4 |
C4—C5—H5 | 119.9 | O4—C17—C18 | 114.8 (4) |
C1—C6—C5 | 121.5 (4) | O4—C17—C16 | 124.8 (4) |
C1—C6—Br1 | 118.7 (3) | C18—C17—C16 | 120.4 (4) |
C5—C6—Br1 | 119.8 (3) | O5—C18—C19 | 118.5 (4) |
C8—C7—C4 | 130.2 (4) | O5—C18—C17 | 123.3 (4) |
C8—C7—H7 | 114.9 | C19—C18—C17 | 118.3 (4) |
C4—C7—H7 | 114.9 | C18—C19—C20 | 121.9 (4) |
C7—C8—C13 | 125.4 (4) | C18—C19—Br2 | 119.3 (3) |
C7—C8—C9 | 115.6 (4) | C20—C19—Br2 | 118.8 (3) |
C13—C8—C9 | 119.0 (4) | C19—C20—C15 | 120.3 (4) |
O3—C9—C10 | 120.7 (4) | C19—C20—H20 | 119.8 |
O3—C9—C8 | 120.6 (4) | C15—C20—H20 | 119.8 |
C10—C9—C8 | 118.7 (4) | O2—C21—H21A | 109.5 |
C14—C10—C9 | 116.2 (4) | O2—C21—H21B | 109.5 |
C14—C10—C11 | 124.7 (4) | H21A—C21—H21B | 109.5 |
C9—C10—C11 | 119.1 (4) | O2—C21—H21C | 109.5 |
C10—C11—C12 | 111.9 (3) | H21A—C21—H21C | 109.5 |
C10—C11—H11A | 109.2 | H21B—C21—H21C | 109.5 |
C12—C11—H11A | 109.2 | O4—C22—H22A | 109.5 |
C10—C11—H11B | 109.2 | O4—C22—H22B | 109.5 |
C12—C11—H11B | 109.2 | H22A—C22—H22B | 109.5 |
H11A—C11—H11B | 107.9 | O4—C22—H22C | 109.5 |
C13—C12—C11 | 110.5 (4) | H22A—C22—H22C | 109.5 |
C13—C12—H12A | 109.5 | H22B—C22—H22C | 109.5 |
C11—C12—H12A | 109.5 | C1—O1—H1 | 109.5 |
C13—C12—H12B | 109.5 | C2—O2—C21 | 120.3 (4) |
C11—C12—H12B | 109.5 | C17—O4—C22 | 118.1 (4) |
H12A—C12—H12B | 108.1 | C18—O5—H5A | 109.5 |
C8—C13—C12 | 113.3 (4) | ||
C6—C1—C2—O2 | 179.2 (4) | C9—C10—C11—C12 | 29.9 (6) |
O1—C1—C2—O2 | −2.1 (6) | C10—C11—C12—C13 | −57.8 (5) |
C6—C1—C2—C3 | −0.8 (7) | C7—C8—C13—C12 | 153.4 (4) |
O1—C1—C2—C3 | 177.9 (4) | C9—C8—C13—C12 | −24.9 (6) |
O2—C2—C3—C4 | −177.8 (4) | C11—C12—C13—C8 | 55.5 (5) |
C1—C2—C3—C4 | 2.1 (7) | C9—C10—C14—C15 | 176.6 (5) |
C2—C3—C4—C5 | −2.4 (6) | C11—C10—C14—C15 | −3.7 (8) |
C2—C3—C4—C7 | 178.6 (4) | C10—C14—C15—C20 | −23.8 (8) |
C3—C4—C5—C6 | 1.4 (7) | C10—C14—C15—C16 | 160.6 (5) |
C7—C4—C5—C6 | −179.8 (4) | C20—C15—C16—C17 | 3.1 (7) |
O1—C1—C6—C5 | −178.9 (4) | C14—C15—C16—C17 | 179.0 (4) |
C2—C1—C6—C5 | −0.3 (7) | C15—C16—C17—O4 | 180.0 (4) |
O1—C1—C6—Br1 | 1.4 (6) | C15—C16—C17—C18 | −0.3 (7) |
C2—C1—C6—Br1 | −179.9 (3) | O4—C17—C18—O5 | −1.5 (7) |
C4—C5—C6—C1 | −0.1 (7) | C16—C17—C18—O5 | 178.8 (4) |
C4—C5—C6—Br1 | 179.6 (3) | O4—C17—C18—C19 | 177.3 (4) |
C5—C4—C7—C8 | 23.3 (8) | C16—C17—C18—C19 | −2.4 (7) |
C3—C4—C7—C8 | −157.9 (5) | O5—C18—C19—C20 | −178.8 (4) |
C4—C7—C8—C13 | −2.0 (8) | C17—C18—C19—C20 | 2.3 (7) |
C4—C7—C8—C9 | 176.4 (5) | O5—C18—C19—Br2 | 2.4 (6) |
C7—C8—C9—O3 | −1.7 (7) | C17—C18—C19—Br2 | −176.4 (3) |
C13—C8—C9—O3 | 176.8 (4) | C18—C19—C20—C15 | 0.6 (7) |
C7—C8—C9—C10 | 178.1 (4) | Br2—C19—C20—C15 | 179.3 (3) |
C13—C8—C9—C10 | −3.3 (6) | C16—C15—C20—C19 | −3.2 (6) |
O3—C9—C10—C14 | 0.2 (7) | C14—C15—C20—C19 | −178.8 (4) |
C8—C9—C10—C14 | −179.7 (4) | C3—C2—O2—C21 | −7.8 (7) |
O3—C9—C10—C11 | −179.6 (4) | C1—C2—O2—C21 | 172.3 (4) |
C8—C9—C10—C11 | 0.6 (6) | C18—C17—O4—C22 | −168.4 (4) |
C14—C10—C11—C12 | −149.8 (5) | C16—C17—O4—C22 | 11.4 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.15 | 2.613 (5) | 115 |
O5—H5A···O1i | 0.84 | 1.98 | 2.796 (5) | 163 |
O1—H1···O4ii | 0.84 | 2.30 | 2.809 (4) | 120 |
O5—H5A···O4 | 0.84 | 2.27 | 2.706 (5) | 113 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C22H20Br2O5 |
Mr | 524.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 7.5550 (11), 14.938 (2), 17.763 (3) |
β (°) | 95.201 (3) |
V (Å3) | 1996.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.09 |
Crystal size (mm) | 0.32 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.354, 0.685 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10131, 4349, 2760 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.110, 1.02 |
No. of reflections | 4349 |
No. of parameters | 266 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −0.54 |
Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.15 | 2.613 (5) | 114.9 |
O5—H5A···O1i | 0.84 | 1.98 | 2.796 (5) | 163.3 |
O1—H1···O4ii | 0.84 | 2.30 | 2.809 (4) | 119.5 |
O5—H5A···O4 | 0.84 | 2.27 | 2.706 (5) | 112.8 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
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Curcumin analogs exhibit potential antioxidative properties (Sardjiman et al., 1997, Youssef et al., 2004) and inhibitory activities on α-glucosidase (Du, Liu et al., 2006) and on aldose reductase (Du, Bao et al., 2006). The title compound, C22H20Br2O5, is a synthesized curcumin analog and we report here its crystal structure.
The X-ray crystallographic study of the title compound confirms the previously proposed molecular structure based on spectroscopic data (Fig. 1). The C—C, C═C, C—O and C═O distances show no remarkable features.
A structural feature is the presence of intermolecular O—H···O hydrogen bonds between the hydroxy groups and the methoxy groups O of neighboring molecules (Table 2), resulting in infinite chains along the c axis (Fig. 2). Furthermore, there is a short intermolecular contact between the carbonyl O atom and a Br atom; Br2···O3 = 3.051 (3) Å.