Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103008679/na1595sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008679/na1595Isup2.hkl |
CCDC reference: 214395
2-Hydroxy-4-methoxyacetophenone was dissolved in ethanol and crushed KOH was added. The flask was immersed in a bath of crushed ice and a solution of 2,3,4-trimethoxybenzaldehyde in ethanol was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 48 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel. Crystals of the title compound were obtained from a mixture of methanol and chlorofom (9:1) by slow evaporation.
All H atoms were fixed geometrically and allowed to ride on their parent atoms, with O—H = 0.82 Å and C—H = 0.93 or 0.96 Å, and Uiso = 1.5 and 1.2Ueq for methyl and other H atoms, respectively.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST(Nardelli, 1995).
C19H20O6 | F(000) = 728 |
Mr = 344.35 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.6025 (6) Å | Cell parameters from 5955 reflections |
b = 8.1908 (2) Å | θ = 3.0–28.3° |
c = 12.6432 (5) Å | µ = 0.10 mm−1 |
β = 92.303 (1)° | T = 293 K |
V = 1717.93 (10) Å3 | Rectangular slab, yellow |
Z = 4 | 0.32 × 0.28 × 0.20 mm |
Siemens SMART CCD area-detector diffractometer | 4236 independent reflections |
Radiation source: fine-focus sealed tube | 2285 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 3.0° |
ω scans | h = −22→22 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→5 |
Tmin = 0.969, Tmax = 0.980 | l = −16→15 |
11685 measured 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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
4236 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C19H20O6 | V = 1717.93 (10) Å3 |
Mr = 344.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.6025 (6) Å | µ = 0.10 mm−1 |
b = 8.1908 (2) Å | T = 293 K |
c = 12.6432 (5) Å | 0.32 × 0.28 × 0.20 mm |
β = 92.303 (1)° |
Siemens SMART CCD area-detector diffractometer | 4236 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2285 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.980 | Rint = 0.063 |
11685 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.20 e Å−3 |
4236 reflections | Δρmin = −0.31 e Å−3 |
226 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 | 0.41006 (8) | 0.45417 (18) | 0.90832 (11) | 0.0593 (4) | |
O2 | 0.44967 (8) | 0.57618 (18) | 0.72241 (12) | 0.0589 (4) | |
O3 | 0.34945 (8) | 0.53234 (17) | 0.54318 (10) | 0.0493 (4) | |
O4 | 0.10647 (9) | 0.4475 (2) | 0.37026 (11) | 0.0665 (5) | |
O5 | −0.01395 (10) | 0.4101 (2) | 0.24713 (11) | 0.0769 (5) | |
H5 | 0.0291 | 0.4490 | 0.2690 | 0.115* | |
O6 | −0.22266 (8) | 0.0603 (2) | 0.35541 (12) | 0.0704 (5) | |
C1 | −0.04430 (11) | 0.3158 (3) | 0.32211 (14) | 0.0482 (5) | |
C2 | −0.11761 (12) | 0.2396 (3) | 0.29813 (15) | 0.0529 (5) | |
H2 | −0.1431 | 0.2541 | 0.2319 | 0.063* | |
C3 | −0.15199 (11) | 0.1437 (3) | 0.37208 (16) | 0.0503 (5) | |
C4 | −0.11468 (11) | 0.1218 (3) | 0.47215 (16) | 0.0549 (5) | |
H4 | −0.1390 | 0.0579 | 0.5226 | 0.066* | |
C5 | −0.04217 (11) | 0.1952 (3) | 0.49522 (14) | 0.0488 (5) | |
H5A | −0.0178 | 0.1802 | 0.5620 | 0.059* | |
C6 | −0.00356 (10) | 0.2920 (2) | 0.42179 (13) | 0.0405 (4) | |
C7 | 0.07524 (11) | 0.3666 (2) | 0.44133 (14) | 0.0446 (5) | |
C8 | 0.12035 (11) | 0.3476 (3) | 0.54290 (15) | 0.0476 (5) | |
H8 | 0.0983 | 0.2888 | 0.5976 | 0.057* | |
C9 | 0.19256 (11) | 0.4146 (2) | 0.55622 (15) | 0.0471 (5) | |
H9 | 0.2114 | 0.4677 | 0.4971 | 0.057* | |
C10 | 0.24714 (11) | 0.4178 (2) | 0.64935 (14) | 0.0436 (5) | |
C11 | 0.22606 (12) | 0.3604 (3) | 0.74776 (16) | 0.0540 (5) | |
H11 | 0.1753 | 0.3145 | 0.7547 | 0.065* | |
C12 | 0.27806 (12) | 0.3694 (3) | 0.83582 (16) | 0.0563 (6) | |
H12 | 0.2624 | 0.3293 | 0.9007 | 0.068* | |
C13 | 0.35371 (11) | 0.4386 (2) | 0.82676 (16) | 0.0475 (5) | |
C14 | 0.37646 (10) | 0.4990 (2) | 0.72976 (15) | 0.0433 (5) | |
C15 | 0.32412 (11) | 0.4864 (2) | 0.64145 (14) | 0.0424 (5) | |
C16 | −0.26436 (13) | 0.0792 (4) | 0.25545 (19) | 0.0790 (8) | |
H16A | −0.3130 | 0.0158 | 0.2543 | 0.118* | |
H16B | −0.2307 | 0.0422 | 0.2003 | 0.118* | |
H16C | −0.2775 | 0.1922 | 0.2443 | 0.118* | |
C17 | 0.39444 (15) | 0.3741 (3) | 1.00528 (17) | 0.0697 (7) | |
H17A | 0.4380 | 0.3945 | 1.0557 | 0.105* | |
H17B | 0.3896 | 0.2587 | 0.9932 | 0.105* | |
H17C | 0.3451 | 0.4149 | 1.0323 | 0.105* | |
C18 | 0.51275 (14) | 0.4777 (4) | 0.6866 (3) | 0.0932 (9) | |
H18A | 0.5612 | 0.5413 | 0.6843 | 0.140* | |
H18B | 0.4986 | 0.4374 | 0.6170 | 0.140* | |
H18C | 0.5214 | 0.3874 | 0.7341 | 0.140* | |
C19 | 0.35802 (15) | 0.7019 (3) | 0.52485 (19) | 0.0710 (7) | |
H19A | 0.3756 | 0.7192 | 0.4543 | 0.107* | |
H19B | 0.3972 | 0.7462 | 0.5749 | 0.107* | |
H19C | 0.3071 | 0.7551 | 0.5330 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0602 (9) | 0.0626 (10) | 0.0537 (9) | −0.0087 (7) | −0.0162 (7) | 0.0054 (7) |
O2 | 0.0438 (8) | 0.0581 (10) | 0.0745 (10) | −0.0144 (7) | 0.0003 (7) | −0.0005 (7) |
O3 | 0.0524 (8) | 0.0481 (9) | 0.0480 (8) | −0.0037 (7) | 0.0098 (6) | 0.0002 (6) |
O4 | 0.0644 (9) | 0.0903 (13) | 0.0445 (8) | −0.0242 (9) | 0.0006 (7) | 0.0088 (8) |
O5 | 0.0924 (12) | 0.1003 (14) | 0.0370 (8) | −0.0345 (10) | −0.0100 (7) | 0.0097 (8) |
O6 | 0.0426 (8) | 0.0952 (13) | 0.0725 (10) | −0.0093 (8) | −0.0074 (7) | −0.0135 (9) |
C1 | 0.0559 (11) | 0.0544 (13) | 0.0340 (9) | −0.0020 (10) | −0.0014 (8) | −0.0057 (9) |
C2 | 0.0551 (12) | 0.0628 (15) | 0.0398 (10) | 0.0027 (11) | −0.0100 (9) | −0.0125 (10) |
C3 | 0.0353 (10) | 0.0589 (14) | 0.0564 (12) | 0.0027 (10) | −0.0004 (9) | −0.0155 (11) |
C4 | 0.0450 (11) | 0.0683 (15) | 0.0514 (11) | −0.0066 (10) | 0.0014 (9) | 0.0064 (11) |
C5 | 0.0437 (10) | 0.0617 (14) | 0.0406 (10) | 0.0000 (10) | −0.0037 (8) | 0.0010 (9) |
C6 | 0.0417 (10) | 0.0465 (12) | 0.0334 (9) | 0.0035 (9) | 0.0008 (7) | −0.0052 (8) |
C7 | 0.0463 (10) | 0.0503 (12) | 0.0373 (10) | −0.0015 (9) | 0.0042 (8) | −0.0041 (9) |
C8 | 0.0451 (10) | 0.0567 (13) | 0.0410 (10) | −0.0027 (10) | −0.0002 (8) | 0.0016 (9) |
C9 | 0.0445 (10) | 0.0532 (13) | 0.0439 (10) | −0.0035 (9) | 0.0033 (8) | −0.0023 (9) |
C10 | 0.0403 (10) | 0.0446 (12) | 0.0458 (10) | −0.0018 (8) | −0.0001 (8) | 0.0002 (9) |
C11 | 0.0440 (11) | 0.0638 (14) | 0.0540 (12) | −0.0144 (10) | 0.0003 (9) | 0.0072 (10) |
C12 | 0.0568 (12) | 0.0648 (15) | 0.0470 (11) | −0.0124 (11) | −0.0017 (9) | 0.0093 (10) |
C13 | 0.0472 (11) | 0.0425 (12) | 0.0519 (11) | −0.0026 (9) | −0.0068 (9) | −0.0003 (9) |
C14 | 0.0398 (10) | 0.0353 (11) | 0.0545 (11) | −0.0032 (8) | −0.0013 (8) | −0.0012 (9) |
C15 | 0.0431 (10) | 0.0378 (11) | 0.0468 (11) | −0.0005 (9) | 0.0075 (8) | 0.0005 (8) |
C16 | 0.0443 (12) | 0.118 (2) | 0.0738 (16) | 0.0003 (13) | −0.0091 (11) | −0.0365 (15) |
C17 | 0.0876 (17) | 0.0651 (16) | 0.0548 (13) | −0.0038 (14) | −0.0169 (12) | 0.0088 (12) |
C18 | 0.0425 (12) | 0.107 (2) | 0.130 (3) | 0.0047 (14) | 0.0032 (14) | 0.0010 (19) |
C19 | 0.0920 (17) | 0.0545 (15) | 0.0677 (14) | 0.0031 (13) | 0.0180 (13) | 0.0133 (12) |
O1—C13 | 1.370 (2) | C8—H8 | 0.9300 |
O1—C17 | 1.423 (2) | C9—C10 | 1.457 (3) |
O2—C14 | 1.376 (2) | C9—H9 | 0.9300 |
O2—C18 | 1.411 (3) | C10—C15 | 1.403 (2) |
O3—C15 | 1.380 (2) | C10—C11 | 1.388 (3) |
O3—C19 | 1.416 (3) | C11—C12 | 1.383 (3) |
O4—C7 | 1.246 (2) | C11—H11 | 0.9300 |
O5—C1 | 1.337 (2) | C12—C13 | 1.387 (3) |
O5—H5 | 0.8200 | C12—H12 | 0.9300 |
O6—C3 | 1.367 (2) | C13—C14 | 1.389 (3) |
O6—C16 | 1.425 (3) | C14—C15 | 1.391 (3) |
C1—C2 | 1.390 (3) | C16—H16A | 0.9600 |
C1—C6 | 1.420 (2) | C16—H16B | 0.9600 |
C2—C3 | 1.364 (3) | C16—H16C | 0.9600 |
C2—H2 | 0.9300 | C17—H17A | 0.9600 |
C3—C4 | 1.398 (3) | C17—H17B | 0.9600 |
C4—C5 | 1.366 (3) | C17—H17C | 0.9600 |
C4—H4 | 0.9300 | C18—H18A | 0.9600 |
C5—C6 | 1.396 (3) | C18—H18B | 0.9600 |
C5—H5A | 0.9300 | C18—H18C | 0.9600 |
C6—C7 | 1.456 (3) | C19—H19A | 0.9600 |
C7—C8 | 1.469 (3) | C19—H19B | 0.9600 |
C8—C9 | 1.323 (3) | C19—H19C | 0.9600 |
C13—O1—C17 | 117.6 (2) | C10—C11—H11 | 118.9 |
C14—O2—C18 | 115.4 (2) | C13—C12—C11 | 119.56 (18) |
C15—O3—C19 | 116.8 (2) | C13—C12—H12 | 120.2 |
C1—O5—H5 | 109.5 | C11—C12—H12 | 120.2 |
C3—O6—C16 | 117.8 (2) | O1—C13—C12 | 124.69 (18) |
O5—C1—C2 | 117.14 (17) | O1—C13—C14 | 115.45 (17) |
O5—C1—C6 | 121.94 (17) | C12—C13—C14 | 119.86 (18) |
C2—C1—C6 | 120.93 (18) | O2—C14—C15 | 120.32 (17) |
C1—C2—C3 | 119.72 (18) | O2—C14—C13 | 119.70 (17) |
C1—C2—H2 | 120.1 | C15—C14—C13 | 119.94 (17) |
C3—C2—H2 | 120.1 | O3—C15—C14 | 119.95 (16) |
O6—C3—C4 | 115.0 (2) | O3—C15—C10 | 119.00 (17) |
O6—C3—C2 | 124.2 (2) | C14—C15—C10 | 120.93 (17) |
C4—C3—C2 | 120.80 (18) | O6—C16—H16A | 109.5 |
C5—C4—C3 | 119.43 (19) | O6—C16—H16B | 109.5 |
C5—C4—H4 | 120.3 | H16A—C16—H16B | 109.5 |
C3—C4—H4 | 120.3 | O6—C16—H16C | 109.5 |
C4—C5—C6 | 122.13 (18) | H16A—C16—H16C | 109.5 |
C4—C5—H5A | 118.9 | H16B—C16—H16C | 109.5 |
C6—C5—H5A | 118.9 | O1—C17—H17A | 109.5 |
C5—C6—C1 | 116.9 (2) | O1—C17—H17B | 109.5 |
C5—C6—C7 | 124.0 (2) | H17A—C17—H17B | 109.5 |
C1—C6—C7 | 119.1 (2) | O1—C17—H17C | 109.5 |
O4—C7—C6 | 119.86 (17) | H17A—C17—H17C | 109.5 |
O4—C7—C8 | 118.34 (17) | H17B—C17—H17C | 109.5 |
C6—C7—C8 | 121.8 (2) | O2—C18—H18A | 109.5 |
C9—C8—C7 | 119.66 (18) | O2—C18—H18B | 109.5 |
C9—C8—H8 | 120.2 | H18A—C18—H18B | 109.5 |
C7—C8—H8 | 120.2 | O2—C18—H18C | 109.5 |
C8—C9—C10 | 129.9 (2) | H18A—C18—H18C | 109.5 |
C8—C9—H9 | 115.1 | H18B—C18—H18C | 109.5 |
C10—C9—H9 | 115.1 | O3—C19—H19A | 109.5 |
C15—C10—C11 | 117.55 (17) | O3—C19—H19B | 109.5 |
C15—C10—C9 | 119.22 (16) | H19A—C19—H19B | 109.5 |
C11—C10—C9 | 123.2 (2) | O3—C19—H19C | 109.5 |
C12—C11—C10 | 122.13 (18) | H19A—C19—H19C | 109.5 |
C12—C11—H11 | 118.9 | H19B—C19—H19C | 109.5 |
O5—C1—C2—C3 | −179.13 (19) | C15—C10—C11—C12 | 0.0 (3) |
C6—C1—C2—C3 | 1.5 (3) | C9—C10—C11—C12 | −177.9 (2) |
C16—O6—C3—C4 | 179.1 (2) | C10—C11—C12—C13 | 0.4 (3) |
C16—O6—C3—C2 | −2.1 (3) | C17—O1—C13—C12 | 9.1 (3) |
C1—C2—C3—O6 | −178.2 (2) | C17—O1—C13—C14 | −171.33 (18) |
C1—C2—C3—C4 | 0.5 (3) | C11—C12—C13—O1 | 179.9 (2) |
O6—C3—C4—C5 | 177.57 (18) | C11—C12—C13—C14 | 0.4 (3) |
C2—C3—C4—C5 | −1.2 (3) | C18—O2—C14—C15 | −85.0 (2) |
C3—C4—C5—C6 | −0.1 (3) | C18—O2—C14—C13 | 97.3 (2) |
C4—C5—C6—C1 | 2.0 (3) | O1—C13—C14—O2 | −3.4 (3) |
C4—C5—C6—C7 | −177.23 (19) | C12—C13—C14—O2 | 176.21 (18) |
O5—C1—C6—C5 | 177.99 (19) | O1—C13—C14—C15 | 178.81 (17) |
C2—C1—C6—C5 | −2.7 (3) | C12—C13—C14—C15 | −1.6 (3) |
O5—C1—C6—C7 | −2.8 (3) | C19—O3—C15—C14 | −72.7 (2) |
C2—C1—C6—C7 | 176.54 (18) | C19—O3—C15—C10 | 111.3 (2) |
C5—C6—C7—O4 | 177.93 (19) | O2—C14—C15—O3 | 8.3 (3) |
C1—C6—C7—O4 | −1.3 (3) | C13—C14—C15—O3 | −173.94 (17) |
C5—C6—C7—C8 | −1.2 (3) | O2—C14—C15—C10 | −175.73 (17) |
C1—C6—C7—C8 | 179.64 (18) | C13—C14—C15—C10 | 2.0 (3) |
O4—C7—C8—C9 | −0.6 (3) | C11—C10—C15—O3 | 174.77 (18) |
C6—C7—C8—C9 | 178.5 (2) | C9—C10—C15—O3 | −7.2 (3) |
C7—C8—C9—C10 | 177.6 (2) | C11—C10—C15—C14 | −1.2 (3) |
C8—C9—C10—C15 | 175.0 (2) | C9—C10—C15—C14 | 176.80 (18) |
C8—C9—C10—C11 | −7.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.82 | 1.78 | 2.503 (2) | 147 |
C9—H9···O4 | 0.93 | 2.33 | 2.715 (2) | 105 |
C9—H9···O3 | 0.93 | 2.40 | 2.789 (2) | 105 |
C19—H19B···O2 | 0.96 | 2.46 | 3.051 (3) | 120 |
C5—H5A···O5i | 0.93 | 2.45 | 3.315 (2) | 154 |
C17—H17B···O3i | 0.96 | 2.56 | 3.449 (3) | 154 |
C19—H19C···O6ii | 0.96 | 2.53 | 3.378 (3) | 147 |
C16—H16B···O4iii | 0.96 | 2.41 | 3.301 (3) | 155 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20O6 |
Mr | 344.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.6025 (6), 8.1908 (2), 12.6432 (5) |
β (°) | 92.303 (1) |
V (Å3) | 1717.93 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.32 × 0.28 × 0.20 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.969, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11685, 4236, 2285 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.148, 1.02 |
No. of reflections | 4236 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.31 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST(Nardelli, 1995).
O1—C13 | 1.370 (2) | O4—C7 | 1.246 (2) |
O1—C17 | 1.423 (2) | O5—C1 | 1.337 (2) |
O2—C14 | 1.376 (2) | O6—C3 | 1.367 (2) |
O2—C18 | 1.411 (3) | O6—C16 | 1.425 (3) |
O3—C15 | 1.380 (2) | C8—C9 | 1.323 (3) |
O3—C19 | 1.416 (3) | ||
C13—O1—C17 | 117.6 (2) | C5—C6—C1 | 116.9 (2) |
C14—O2—C18 | 115.4 (2) | C5—C6—C7 | 124.0 (2) |
C15—O3—C19 | 116.8 (2) | C1—C6—C7 | 119.1 (2) |
C3—O6—C16 | 117.8 (2) | C6—C7—C8 | 121.8 (2) |
O6—C3—C4 | 115.0 (2) | C8—C9—C10 | 129.9 (2) |
O6—C3—C2 | 124.2 (2) | C11—C10—C9 | 123.2 (2) |
C16—O6—C3—C4 | 179.1 (2) | C7—C8—C9—C10 | 177.6 (2) |
C16—O6—C3—C2 | −2.1 (3) | C8—C9—C10—C15 | 175.0 (2) |
C1—C6—C7—O4 | −1.3 (3) | C17—O1—C13—C12 | 9.1 (3) |
O4—C7—C8—C9 | −0.6 (3) | C18—O2—C14—C13 | 97.3 (2) |
C6—C7—C8—C9 | 178.5 (2) | C19—O3—C15—C14 | −72.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.82 | 1.78 | 2.503 (2) | 147 |
C9—H9···O4 | 0.93 | 2.33 | 2.715 (2) | 105 |
C9—H9···O3 | 0.93 | 2.40 | 2.789 (2) | 105 |
C19—H19B···O2 | 0.96 | 2.46 | 3.051 (3) | 120 |
C5—H5A···O5i | 0.93 | 2.45 | 3.315 (2) | 154 |
C17—H17B···O3i | 0.96 | 2.56 | 3.449 (3) | 154 |
C19—H19C···O6ii | 0.96 | 2.53 | 3.378 (3) | 147 |
C16—H16B···O4iii | 0.96 | 2.41 | 3.301 (3) | 155 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) −x, y−1/2, −z+1/2. |
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Chalcone derivatives possess non-linear optical properties (Fichou et al., 1988). 1,3-Diarylprop-2-enones (chalcones) are of great interest due to their biological activities, viz. antibacterial, antifungal and anti-inflammatory (Ahluwalia et al., 1986; Bhat et al., 1972; Mathew et al., 1984; Oganesyan et al., 1986). They have been widely used as starting materials in many synthetic reactions (Awad et al., 1960; Coudert et al., 1988; Carrie & Rochard, 1963). The main feature of chalcone derivatives is the carbonyl functional group. The carbonyl group plays a significant role in the antibacterial activity of chalcones. Against this background, and in order to obtain detailed information of the solid-state structures, an X-ray study of the title compound, (I), was carried out.
The molecular structure of (I) (Fig. 1) consists of two phenyl rings attached to a propenone group at the 1,3-positions. The molecule is approximately planar, with a dihedral angle between the two phenyl rings of 11.0 (1)°. The two phenyl rings make dihedral angles of 3.5 (1) and 8.6 (1)° with the O4═C7—C8═C9 group. An analysis of the weighted least-squares plane through the central C6—C7(O4)—C8—C9—C10 chain shows that it is planar, with the largest displacement being 0.011 (2) Å for C8. The H atoms at C8 and C9 are trans.
The bond lengths O1—C13, O2—C14, O3—C15, O5—C1, O6—C3, C8═C9 and O4═C7 are comparable with the corresponding values in a similar structure (Sharma et al., 1997). The O1 and O6 methoxy groups, which are both in para positions with respect to the point of attachment of the central chain to the benzene rings, show the tendency observed for anisoles to be coplanar with their attached benzene rings; they are oriented in opposite directions with respect to the central chain. The two methoxy groups (O2 and O3) adjacent to O1 are nearly perpendicular and directed on opposite sides of their attached benzene ring. This is obviously due to steric hindrance, the O2···O3 contact distance being 2.780 (2) Å. The orientation of the O3 group is determined by the presence of the adjacent O2 group [O1···O2 = 2.661 (2) Å], while that of the O6 group involves a H16B···H2 contact of 2.29 Å.
The average O—Car [1.373 (3) Å] and O—Csp3 [1.420 (3) Å] bond distances agree well with the corresponding literature values of 1.375 (3) and 1.421 (6) Å, respectively (Domiano et al., 1979). The C—O distances of the two methoxy groups orthogonal to the benzene rings are systematically different: O2—C18 and O3—C19 [average 1.414 (4) Å] tend to be shorter than O1—C17 and O6—C16 [average 1.424 (4) Å], while O2—C14 and O3—C15 [average 1.378 (3) Å] tend to be longer than O1—C13 and O6—C3 [average 1.368 (3) Å]. These differences can be interpreted as due to reduced phenyl–O atom conjugation for the orthogonal O2 and O3 methoxy groups with respect to the nearly coplanar O1 and O6 groups.
Both pairs of exocyclic angles, viz. C1—C6—C7/C5—C6—C7 of 119.1 (2)/124.0 (2)° and C15—C10—C9/C11—C10—C9 of 119.2 (2)/123.2 (2)°, are asymmetric and this is due to the H5A···H8 (2.15 Å) and H11···H8 (2.33 Å) repulsive contacts for those larger than 120°, while those narrower are due to the O5—H5···O4 and C9—H9···O3 attractive contacts. The C1—C6—C5 [116.9 (2)°] and C11—C10—C15 [117.6 (2)°] endocyclic angles at the points of attachment of the benzene rings to the central chain are less than 120° because of hybridization and VSEPR (valence-shell electron-pair repulsion) effects (Domenicano et al., 1975a,b). The deformation of the endocyclic angles is quite similar in the two benzene rings. Interestingly, the endocyclic angles of the two benzene rings are practically equal according to the following values: C1/C15 120.9 (2)/120.9 (2)°, C2/C14 119.7 (2)/119.9 (2)°, C3/C13 120.8 (2)/119.9 (2)°, C4/C12 119.4 (2)/119.6 (2)°, C5/C11 122.1 (2)/122.1 (2)° and C6/C10 116.9 (2)/117.6 (2)°. This finding is indicative of similar behaviour on the ring deformation exerted by the corresponding substitution.
In the solid state, the title molecule is characterized by an intramolecular O5—H5···O4 hydrogen bond in which the hydroxy O atom acts as a donor to the adjacent keto O atom. This hydrogen bond is responsible for the coplanarity of the C1–C6 phenyl with the central propenone chain. This hydrogen bond completes a six-membered ring with atoms O4, C7, C6, C1 and O5 [graph-set descriptor S(6); Bernstein et al., 1995], which adopts a planar conformation.
In addition to normal van der Waals interactions, the crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. Atoms C5 and C17 in the molecule at (x, y, z) act as hydrogen-bond donors to O5 and O3 in the molecule at (x, 1/2 − y, 1/2 + z), respectively. These two hydrogen bonds form an R22(22) ring. The molecules at (x, y, z) and (-x, 1 − y, 1 − z) are linked by C19—H19C···O6 hydrogen bonds into cyclic centrosymmetric R22(26) dimers. Atom C16 in the molecule at (x, y, z) donates one proton to atom O4 in the molecule at (-x, −1/2 + y, 1/2 − z), forming a C(9) chain. Thus, the symmetry-related molecules cross-linked by these hydrogen bonds generate a three-dimensional network (Fig. 2). The geometric details of the hydrogen bonds are given in Table 2.