Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041773/hb2521sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041773/hb2521Isup2.hkl |
CCDC reference: 660378
Genistein (0.41 g, 1.5 mmol), iodomethane (0.62 ml, 6 mmol) and potassium carbonate (0.14 g, 1 mmol) in 50 ml of dry acetone were sonicated. After the completion of reaction, the mixture was cooled to room temperature and filtered. The filtrate was distilled to give a yellow solid, which was washed with aqueous saturated sodium bicarbonate twice. The solid was dissolved in acetone (15 ml) and stirred for about 10 min to give a clear solution. After keeping the solution in air for 10 d, colourless blocks of (I) were formed at the bottom of the vesssl on slow evaporation of the solvent. They were collected, washed three times with acetone and dried in a vacuum desiccator using CaCl2 (yield = 88%).
All H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Genistein derivatives show various biological activitites (Kim et al., 2004; Li et al., 2006). In the genistein-related title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angle between the least-squares planes of the two benzene rings (C2—C7 and C1—C15) is 59.25 (6) °. The crystal packing is stabilized by van der Waals forces.
For reference structural data, see: Allen et al. (1987). For background, see: Kim et al. (2004); Li et al. (2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms). |
C18H16O5 | Z = 2 |
Mr = 312.31 | F(000) = 328 |
Triclinic, P1 | Dx = 1.374 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5649 (10) Å | Cell parameters from 1220 reflections |
b = 10.3212 (13) Å | θ = 2.5–25.5° |
c = 10.5563 (13) Å | µ = 0.10 mm−1 |
α = 63.783 (2)° | T = 298 K |
β = 71.937 (2)° | Block, colorless |
γ = 65.953 (2)° | 0.20 × 0.15 × 0.15 mm |
V = 754.83 (16) Å3 |
Bruker SMART CCD diffractometer | 2855 independent reflections |
Radiation source: fine-focus sealed tube | 2134 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→10 |
Tmin = 0.980, Tmax = 0.985 | k = −12→12 |
4140 measured reflections | l = −13→12 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.0778P] where P = (Fo2 + 2Fc2)/3 |
2855 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C18H16O5 | γ = 65.953 (2)° |
Mr = 312.31 | V = 754.83 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5649 (10) Å | Mo Kα radiation |
b = 10.3212 (13) Å | µ = 0.10 mm−1 |
c = 10.5563 (13) Å | T = 298 K |
α = 63.783 (2)° | 0.20 × 0.15 × 0.15 mm |
β = 71.937 (2)° |
Bruker SMART CCD diffractometer | 2855 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2134 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.985 | Rint = 0.016 |
4140 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.16 e Å−3 |
2855 reflections | Δρmin = −0.24 e Å−3 |
211 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 | ||
C1 | 0.4469 (2) | 0.3920 (2) | 0.7581 (2) | 0.0375 (5) | |
C2 | 0.4112 (2) | 0.2474 (2) | 0.8110 (2) | 0.0338 (4) | |
C3 | 0.2547 (2) | 0.2205 (2) | 0.8986 (2) | 0.0365 (5) | |
C4 | 0.2282 (2) | 0.0844 (2) | 0.9375 (2) | 0.0408 (5) | |
H4 | 0.1239 | 0.0702 | 0.9921 | 0.049* | |
C5 | 0.3565 (3) | −0.0329 (2) | 0.8960 (2) | 0.0389 (5) | |
C6 | 0.5120 (3) | −0.0150 (2) | 0.8167 (2) | 0.0411 (5) | |
H6 | 0.5987 | −0.0931 | 0.7900 | 0.049* | |
C7 | 0.5355 (2) | 0.1237 (2) | 0.7778 (2) | 0.0359 (4) | |
C8 | 0.7358 (3) | 0.2583 (2) | 0.6647 (2) | 0.0485 (6) | |
H8 | 0.8475 | 0.2585 | 0.6183 | 0.058* | |
C9 | 0.6278 (2) | 0.3838 (2) | 0.6895 (2) | 0.0381 (5) | |
C10 | 0.6923 (2) | 0.5133 (2) | 0.6466 (2) | 0.0376 (5) | |
C11 | 0.8407 (3) | 0.4916 (2) | 0.6911 (2) | 0.0493 (5) | |
H11 | 0.8984 | 0.3953 | 0.7502 | 0.059* | |
C12 | 0.9041 (3) | 0.6105 (2) | 0.6491 (3) | 0.0497 (6) | |
H12 | 1.0027 | 0.5941 | 0.6810 | 0.060* | |
C13 | 0.8212 (2) | 0.7534 (2) | 0.5600 (2) | 0.0393 (5) | |
C14 | 0.6747 (2) | 0.7777 (2) | 0.5130 (2) | 0.0431 (5) | |
H14 | 0.6192 | 0.8736 | 0.4517 | 0.052* | |
C15 | 0.6110 (2) | 0.6575 (2) | 0.5581 (2) | 0.0422 (5) | |
H15 | 0.5108 | 0.6748 | 0.5278 | 0.051* | |
C16 | −0.0023 (3) | 0.3017 (3) | 1.0530 (3) | 0.0615 (7) | |
H16A | −0.0738 | 0.2767 | 1.0187 | 0.092* | |
H16B | −0.0698 | 0.3891 | 1.0792 | 0.092* | |
H16C | 0.0419 | 0.2170 | 1.1350 | 0.092* | |
C17 | 0.4422 (3) | −0.2884 (2) | 0.9073 (3) | 0.0600 (6) | |
H17A | 0.4685 | −0.2596 | 0.8052 | 0.090* | |
H17B | 0.3976 | −0.3725 | 0.9482 | 0.090* | |
H17C | 0.5455 | −0.3178 | 0.9445 | 0.090* | |
C18 | 0.8265 (3) | 1.0087 (3) | 0.4181 (3) | 0.0612 (7) | |
H18A | 0.8342 | 0.9953 | 0.3318 | 0.092* | |
H18B | 0.8923 | 1.0733 | 0.3992 | 0.092* | |
H18C | 0.7076 | 1.0548 | 0.4520 | 0.092* | |
O1 | 0.33992 (18) | 0.51091 (16) | 0.76789 (19) | 0.0600 (5) | |
O2 | 0.13918 (17) | 0.33485 (15) | 0.94267 (16) | 0.0493 (4) | |
O3 | 0.31532 (18) | −0.16221 (15) | 0.94307 (17) | 0.0519 (4) | |
O4 | 0.69615 (17) | 0.13026 (15) | 0.70162 (17) | 0.0510 (4) | |
O5 | 0.89364 (17) | 0.86501 (16) | 0.52360 (17) | 0.0500 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0365 (10) | 0.0374 (11) | 0.0389 (11) | −0.0124 (9) | 0.0012 (8) | −0.0184 (9) |
C2 | 0.0336 (10) | 0.0345 (10) | 0.0344 (10) | −0.0110 (8) | −0.0029 (8) | −0.0150 (8) |
C3 | 0.0348 (10) | 0.0345 (10) | 0.0413 (11) | −0.0104 (8) | −0.0028 (8) | −0.0175 (8) |
C4 | 0.0365 (11) | 0.0416 (11) | 0.0472 (12) | −0.0169 (9) | −0.0002 (9) | −0.0186 (9) |
C5 | 0.0462 (11) | 0.0334 (10) | 0.0402 (11) | −0.0154 (9) | −0.0079 (9) | −0.0128 (9) |
C6 | 0.0444 (12) | 0.0330 (10) | 0.0446 (12) | −0.0072 (9) | −0.0060 (9) | −0.0183 (9) |
C7 | 0.0349 (10) | 0.0359 (10) | 0.0353 (10) | −0.0110 (8) | −0.0012 (8) | −0.0146 (8) |
C8 | 0.0367 (11) | 0.0445 (12) | 0.0607 (14) | −0.0183 (9) | 0.0093 (10) | −0.0223 (11) |
C9 | 0.0361 (10) | 0.0395 (11) | 0.0377 (11) | −0.0145 (8) | −0.0006 (8) | −0.0145 (9) |
C10 | 0.0329 (10) | 0.0422 (11) | 0.0377 (11) | −0.0148 (8) | 0.0024 (8) | −0.0171 (9) |
C11 | 0.0435 (12) | 0.0431 (12) | 0.0543 (13) | −0.0127 (9) | −0.0129 (10) | −0.0092 (10) |
C12 | 0.0380 (11) | 0.0512 (13) | 0.0626 (14) | −0.0154 (10) | −0.0136 (10) | −0.0180 (11) |
C13 | 0.0331 (10) | 0.0434 (11) | 0.0434 (11) | −0.0174 (9) | 0.0033 (8) | −0.0188 (9) |
C14 | 0.0380 (11) | 0.0407 (11) | 0.0451 (12) | −0.0137 (9) | −0.0067 (9) | −0.0099 (9) |
C15 | 0.0345 (10) | 0.0483 (12) | 0.0445 (12) | −0.0159 (9) | −0.0065 (9) | −0.0149 (10) |
C16 | 0.0504 (13) | 0.0597 (15) | 0.0775 (17) | −0.0275 (11) | 0.0240 (12) | −0.0411 (13) |
C17 | 0.0688 (16) | 0.0355 (12) | 0.0774 (17) | −0.0156 (11) | −0.0080 (13) | −0.0253 (12) |
C18 | 0.0598 (14) | 0.0489 (13) | 0.0766 (18) | −0.0280 (11) | −0.0104 (13) | −0.0148 (12) |
O1 | 0.0452 (9) | 0.0401 (8) | 0.0895 (13) | −0.0177 (7) | 0.0184 (8) | −0.0344 (8) |
O2 | 0.0397 (8) | 0.0420 (8) | 0.0658 (10) | −0.0188 (6) | 0.0165 (7) | −0.0305 (7) |
O3 | 0.0555 (9) | 0.0361 (8) | 0.0683 (10) | −0.0195 (7) | −0.0031 (7) | −0.0225 (7) |
O4 | 0.0408 (8) | 0.0418 (8) | 0.0638 (10) | −0.0142 (6) | 0.0141 (7) | −0.0275 (7) |
O5 | 0.0423 (8) | 0.0452 (8) | 0.0665 (10) | −0.0205 (7) | −0.0061 (7) | −0.0194 (8) |
C1—O1 | 1.222 (2) | C11—H11 | 0.9300 |
C1—C2 | 1.471 (3) | C12—C13 | 1.378 (3) |
C1—C9 | 1.478 (3) | C12—H12 | 0.9300 |
C2—C7 | 1.393 (2) | C13—O5 | 1.379 (2) |
C2—C3 | 1.427 (3) | C13—C14 | 1.380 (3) |
C3—O2 | 1.355 (2) | C14—C15 | 1.390 (3) |
C3—C4 | 1.373 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.397 (3) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—O2 | 1.433 (3) |
C5—O3 | 1.357 (2) | C16—H16A | 0.9600 |
C5—C6 | 1.372 (3) | C16—H16B | 0.9600 |
C6—C7 | 1.386 (3) | C16—H16C | 0.9600 |
C6—H6 | 0.9300 | C17—O3 | 1.430 (2) |
C7—O4 | 1.374 (2) | C17—H17A | 0.9600 |
C8—C9 | 1.332 (3) | C17—H17B | 0.9600 |
C8—O4 | 1.358 (2) | C17—H17C | 0.9600 |
C8—H8 | 0.9300 | C18—O5 | 1.419 (3) |
C9—C10 | 1.486 (3) | C18—H18A | 0.9600 |
C10—C15 | 1.380 (3) | C18—H18B | 0.9600 |
C10—C11 | 1.390 (3) | C18—H18C | 0.9600 |
C11—C12 | 1.382 (3) | ||
O1—C1—C2 | 124.71 (17) | C13—C12—H12 | 120.0 |
O1—C1—C9 | 121.14 (18) | C11—C12—H12 | 120.0 |
C2—C1—C9 | 114.15 (15) | C12—C13—O5 | 116.05 (17) |
C7—C2—C3 | 115.23 (17) | C12—C13—C14 | 119.94 (18) |
C7—C2—C1 | 120.16 (17) | O5—C13—C14 | 124.01 (18) |
C3—C2—C1 | 124.60 (16) | C13—C14—C15 | 119.33 (18) |
O2—C3—C4 | 123.17 (18) | C13—C14—H14 | 120.3 |
O2—C3—C2 | 115.90 (16) | C15—C14—H14 | 120.3 |
C4—C3—C2 | 120.91 (17) | C10—C15—C14 | 121.74 (18) |
C3—C4—C5 | 120.67 (18) | C10—C15—H15 | 119.1 |
C3—C4—H4 | 119.7 | C14—C15—H15 | 119.1 |
C5—C4—H4 | 119.7 | O2—C16—H16A | 109.5 |
O3—C5—C6 | 124.45 (17) | O2—C16—H16B | 109.5 |
O3—C5—C4 | 114.90 (18) | H16A—C16—H16B | 109.5 |
C6—C5—C4 | 120.63 (18) | O2—C16—H16C | 109.5 |
C5—C6—C7 | 117.72 (17) | H16A—C16—H16C | 109.5 |
C5—C6—H6 | 121.1 | H16B—C16—H16C | 109.5 |
C7—C6—H6 | 121.1 | O3—C17—H17A | 109.5 |
O4—C7—C6 | 113.70 (16) | O3—C17—H17B | 109.5 |
O4—C7—C2 | 121.58 (17) | H17A—C17—H17B | 109.5 |
C6—C7—C2 | 124.72 (18) | O3—C17—H17C | 109.5 |
C9—C8—O4 | 125.33 (18) | H17A—C17—H17C | 109.5 |
C9—C8—H8 | 117.3 | H17B—C17—H17C | 109.5 |
O4—C8—H8 | 117.3 | O5—C18—H18A | 109.5 |
C8—C9—C1 | 119.66 (18) | O5—C18—H18B | 109.5 |
C8—C9—C10 | 118.99 (17) | H18A—C18—H18B | 109.5 |
C1—C9—C10 | 121.35 (16) | O5—C18—H18C | 109.5 |
C15—C10—C11 | 117.72 (18) | H18A—C18—H18C | 109.5 |
C15—C10—C9 | 121.51 (17) | H18B—C18—H18C | 109.5 |
C11—C10—C9 | 120.74 (18) | C3—O2—C16 | 117.51 (16) |
C12—C11—C10 | 121.22 (19) | C5—O3—C17 | 117.94 (17) |
C12—C11—H11 | 119.4 | C8—O4—C7 | 118.44 (14) |
C10—C11—H11 | 119.4 | C13—O5—C18 | 118.07 (16) |
C13—C12—C11 | 120.04 (19) | ||
O1—C1—C2—C7 | 171.3 (2) | C2—C1—C9—C10 | −172.17 (16) |
C9—C1—C2—C7 | −8.5 (3) | C8—C9—C10—C15 | 124.8 (2) |
O1—C1—C2—C3 | −9.5 (3) | C1—C9—C10—C15 | −54.9 (3) |
C9—C1—C2—C3 | 170.60 (17) | C8—C9—C10—C11 | −53.1 (3) |
C7—C2—C3—O2 | 174.17 (16) | C1—C9—C10—C11 | 127.1 (2) |
C1—C2—C3—O2 | −5.0 (3) | C15—C10—C11—C12 | 0.5 (3) |
C7—C2—C3—C4 | −4.1 (3) | C9—C10—C11—C12 | 178.5 (2) |
C1—C2—C3—C4 | 176.71 (18) | C10—C11—C12—C13 | −0.8 (3) |
O2—C3—C4—C5 | −176.06 (18) | C11—C12—C13—O5 | −179.94 (19) |
C2—C3—C4—C5 | 2.1 (3) | C11—C12—C13—C14 | 0.1 (3) |
C3—C4—C5—O3 | 179.07 (17) | C12—C13—C14—C15 | 0.9 (3) |
C3—C4—C5—C6 | 0.6 (3) | O5—C13—C14—C15 | −179.00 (18) |
O3—C5—C6—C7 | −179.33 (18) | C11—C10—C15—C14 | 0.6 (3) |
C4—C5—C6—C7 | −1.0 (3) | C9—C10—C15—C14 | −177.37 (18) |
C5—C6—C7—O4 | 178.55 (17) | C13—C14—C15—C10 | −1.3 (3) |
C5—C6—C7—C2 | −1.3 (3) | C4—C3—O2—C16 | 10.6 (3) |
C3—C2—C7—O4 | −176.04 (16) | C2—C3—O2—C16 | −167.67 (19) |
C1—C2—C7—O4 | 3.2 (3) | C6—C5—O3—C17 | −0.2 (3) |
C3—C2—C7—C6 | 3.8 (3) | C4—C5—O3—C17 | −178.62 (18) |
C1—C2—C7—C6 | −176.97 (17) | C9—C8—O4—C7 | −3.9 (3) |
O4—C8—C9—C1 | −2.2 (3) | C6—C7—O4—C8 | −176.59 (18) |
O4—C8—C9—C10 | 178.07 (19) | C2—C7—O4—C8 | 3.3 (3) |
O1—C1—C9—C8 | −171.8 (2) | C12—C13—O5—C18 | 172.12 (19) |
C2—C1—C9—C8 | 8.1 (3) | C14—C13—O5—C18 | −7.9 (3) |
O1—C1—C9—C10 | 8.0 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H16O5 |
Mr | 312.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.5649 (10), 10.3212 (13), 10.5563 (13) |
α, β, γ (°) | 63.783 (2), 71.937 (2), 65.953 (2) |
V (Å3) | 754.83 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.980, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4140, 2855, 2134 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.145, 1.03 |
No. of reflections | 2855 |
No. of parameters | 211 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.24 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXL97.
Genistein derivatives show various biological activitites (Kim et al., 2004; Li et al., 2006). In the genistein-related title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angle between the least-squares planes of the two benzene rings (C2—C7 and C1—C15) is 59.25 (6) °. The crystal packing is stabilized by van der Waals forces.