Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029648/lh6493sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029648/lh6493Isup2.hkl |
CCDC reference: 287623
The title compound was obtained from phloroglucinol via the Hoesch reaction (Gulati et al., 1943), etherification (Juntend & Junte, 1988), Aldol condensation (Bu et al., 1997) and the Mannich reaction (Wilds et al., 1963). A crystal suitable for crystallographic study was obtained by slow crystallization from acetone at room temperature.
All C-bound H atoms were positioned geometrically and allowed to ride on their attached atoms, with C—H(CH), C—H(CH2) and C—H(CH3) distances of 0.93, 0.97 and 0.96 Å, respectively. The isotropic displacement parameters of the H atoms were fixed at 1.2Ueq of their parent atoms. The small ratio of observed to unique reflections (39%) can lower the precision of the structure. Treatment of OH group?
Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
C22H24ClNO5 | F(000) = 1760 |
Mr = 417.89 | Dx = 1.336 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 28 reflections |
a = 13.408 (2) Å | θ = 2.9–14.8° |
b = 10.517 (2) Å | µ = 0.22 mm−1 |
c = 29.505 (6) Å | T = 296 K |
β = 92.90 (2)° | Plate, yellow |
V = 4154.9 (13) Å3 | 0.60 × 0.50 × 0.12 mm |
Z = 8 |
Siemens P4 diffractometer | 1515 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.5°, θmin = 1.4° |
ω scans | h = 0→16 |
Absorption correction: ψ scan (SHELXTL; Bruker, 1997) | k = 0→12 |
Tmin = 0.874, Tmax = 0.974 | l = −35→35 |
4451 measured reflections | 3 standard reflections every 97 reflections |
3872 independent reflections | intensity decay: 3.3% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0262P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max < 0.001 |
3872 reflections | Δρmax = 0.17 e Å−3 |
269 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00184 (12) |
C22H24ClNO5 | V = 4154.9 (13) Å3 |
Mr = 417.89 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.408 (2) Å | µ = 0.22 mm−1 |
b = 10.517 (2) Å | T = 296 K |
c = 29.505 (6) Å | 0.60 × 0.50 × 0.12 mm |
β = 92.90 (2)° |
Siemens P4 diffractometer | 1515 reflections with I > 2σ(I) |
Absorption correction: ψ scan (SHELXTL; Bruker, 1997) | Rint = 0.033 |
Tmin = 0.874, Tmax = 0.974 | 3 standard reflections every 97 reflections |
4451 measured reflections | intensity decay: 3.3% |
3872 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.17 e Å−3 |
3872 reflections | Δρmin = −0.17 e Å−3 |
269 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 | ||
Cl | 0.38905 (6) | 0.72256 (10) | 0.55745 (3) | 0.0884 (4) | |
O1 | 0.63199 (16) | 0.8432 (2) | 0.17539 (7) | 0.0707 (7) | |
O2 | 0.60487 (15) | 0.8428 (2) | 0.43680 (7) | 0.0730 (7) | |
O3 | 0.81469 (14) | 0.5530 (2) | 0.44309 (7) | 0.0615 (6) | |
O4 | 0.95185 (14) | 0.7210 (2) | 0.30864 (6) | 0.0609 (6) | |
O5 | 0.66999 (16) | 0.9096 (2) | 0.36435 (7) | 0.0604 (7) | |
N | 0.76459 (17) | 0.8451 (2) | 0.25467 (8) | 0.0479 (7) | |
C1 | 0.4764 (2) | 0.6039 (3) | 0.57022 (10) | 0.0577 (9) | |
C2 | 0.4576 (3) | 0.5230 (4) | 0.60567 (11) | 0.0725 (11) | |
H2 | 0.4007 | 0.5340 | 0.6220 | 0.087* | |
C3 | 0.5227 (3) | 0.4269 (4) | 0.61656 (12) | 0.0839 (12) | |
H3 | 0.5103 | 0.3728 | 0.6406 | 0.101* | |
C4 | 0.6066 (3) | 0.4092 (3) | 0.59233 (12) | 0.0764 (11) | |
H4 | 0.6510 | 0.3437 | 0.5998 | 0.092* | |
C5 | 0.6239 (2) | 0.4908 (3) | 0.55662 (11) | 0.0623 (10) | |
H5 | 0.6809 | 0.4790 | 0.5404 | 0.075* | |
C6 | 0.5596 (2) | 0.5889 (3) | 0.54432 (10) | 0.0474 (8) | |
C7 | 0.5788 (2) | 0.6735 (3) | 0.50628 (9) | 0.0520 (9) | |
H7 | 0.5357 | 0.7420 | 0.5016 | 0.062* | |
C8 | 0.6509 (2) | 0.6616 (3) | 0.47827 (9) | 0.0510 (8) | |
H8 | 0.6961 | 0.5951 | 0.4826 | 0.061* | |
C9 | 0.6629 (2) | 0.7495 (3) | 0.44013 (9) | 0.0484 (8) | |
C10 | 0.73842 (19) | 0.7318 (3) | 0.40638 (9) | 0.0376 (7) | |
C11 | 0.8143 (2) | 0.6384 (3) | 0.40846 (9) | 0.0438 (8) | |
C12 | 0.88623 (19) | 0.6339 (3) | 0.37645 (9) | 0.0446 (8) | |
H12 | 0.9368 | 0.5733 | 0.3788 | 0.054* | |
C13 | 0.8825 (2) | 0.7198 (3) | 0.34101 (9) | 0.0438 (8) | |
C14 | 0.8086 (2) | 0.8115 (3) | 0.33573 (9) | 0.0415 (8) | |
C15 | 0.7394 (2) | 0.8170 (3) | 0.36919 (9) | 0.0444 (8) | |
C16 | 0.8082 (2) | 0.9018 (3) | 0.29663 (9) | 0.0496 (8) | |
H16A | 0.7703 | 0.9770 | 0.3039 | 0.060* | |
H16B | 0.8761 | 0.9281 | 0.2918 | 0.060* | |
C17 | 0.7802 (2) | 0.9274 (3) | 0.21557 (10) | 0.0706 (10) | |
H17A | 0.8511 | 0.9411 | 0.2126 | 0.085* | |
H17B | 0.7488 | 1.0093 | 0.2200 | 0.085* | |
C18 | 0.7359 (2) | 0.8658 (4) | 0.17340 (11) | 0.0826 (12) | |
H18A | 0.7473 | 0.9201 | 0.1476 | 0.099* | |
H18B | 0.7696 | 0.7856 | 0.1687 | 0.099* | |
C19 | 0.6156 (2) | 0.7666 (3) | 0.21359 (10) | 0.0646 (10) | |
H19A | 0.6457 | 0.6838 | 0.2093 | 0.077* | |
H19B | 0.5444 | 0.7543 | 0.2160 | 0.077* | |
C20 | 0.6583 (2) | 0.8237 (3) | 0.25688 (9) | 0.0577 (9) | |
H20A | 0.6252 | 0.9039 | 0.2624 | 0.069* | |
H20B | 0.6462 | 0.7671 | 0.2820 | 0.069* | |
C21 | 0.8948 (2) | 0.4643 (3) | 0.44885 (10) | 0.0739 (11) | |
H21A | 0.8976 | 0.4125 | 0.4222 | 0.089* | |
H21B | 0.8842 | 0.4113 | 0.4746 | 0.089* | |
H21C | 0.9567 | 0.5096 | 0.4536 | 0.089* | |
C22 | 1.0320 (2) | 0.6316 (3) | 0.31209 (10) | 0.0671 (10) | |
H22A | 1.0697 | 0.6441 | 0.3403 | 0.080* | |
H22B | 1.0747 | 0.6439 | 0.2873 | 0.080* | |
H22C | 1.0055 | 0.5468 | 0.3110 | 0.080* | |
H0 | 0.633 (2) | 0.906 (3) | 0.3890 (11) | 0.103 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0718 (6) | 0.1093 (8) | 0.0870 (7) | 0.0171 (6) | 0.0326 (5) | 0.0079 (7) |
O1 | 0.0693 (16) | 0.0889 (18) | 0.0537 (14) | 0.0189 (14) | 0.0023 (12) | 0.0085 (14) |
O2 | 0.0728 (16) | 0.0699 (16) | 0.0794 (17) | 0.0344 (14) | 0.0339 (13) | 0.0229 (14) |
O3 | 0.0589 (13) | 0.0611 (15) | 0.0660 (15) | 0.0247 (12) | 0.0188 (11) | 0.0227 (13) |
O4 | 0.0526 (13) | 0.0702 (16) | 0.0619 (14) | 0.0138 (12) | 0.0228 (11) | 0.0119 (12) |
O5 | 0.0610 (14) | 0.0611 (16) | 0.0602 (16) | 0.0252 (13) | 0.0149 (13) | 0.0149 (13) |
N | 0.0465 (16) | 0.0579 (17) | 0.0398 (15) | 0.0049 (14) | 0.0071 (12) | 0.0111 (14) |
C1 | 0.060 (2) | 0.070 (3) | 0.044 (2) | −0.008 (2) | 0.0094 (17) | 0.0005 (19) |
C2 | 0.070 (3) | 0.098 (3) | 0.050 (2) | −0.017 (2) | 0.011 (2) | 0.007 (2) |
C3 | 0.095 (3) | 0.101 (4) | 0.055 (3) | −0.027 (3) | −0.006 (2) | 0.022 (2) |
C4 | 0.089 (3) | 0.069 (3) | 0.069 (3) | −0.003 (2) | −0.011 (2) | 0.018 (2) |
C5 | 0.066 (2) | 0.067 (3) | 0.054 (2) | −0.001 (2) | 0.0027 (19) | 0.005 (2) |
C6 | 0.054 (2) | 0.047 (2) | 0.0407 (18) | −0.0059 (18) | 0.0040 (16) | −0.0011 (17) |
C7 | 0.0490 (19) | 0.055 (2) | 0.053 (2) | 0.0050 (17) | 0.0067 (16) | −0.0006 (18) |
C8 | 0.0486 (18) | 0.055 (2) | 0.050 (2) | 0.0147 (17) | 0.0114 (16) | 0.0083 (17) |
C9 | 0.0451 (18) | 0.056 (2) | 0.045 (2) | 0.0017 (18) | 0.0058 (15) | 0.0010 (18) |
C10 | 0.0382 (16) | 0.0392 (18) | 0.0354 (16) | 0.0072 (15) | 0.0036 (13) | 0.0019 (15) |
C11 | 0.0452 (18) | 0.044 (2) | 0.0424 (19) | 0.0022 (16) | 0.0019 (16) | 0.0033 (17) |
C12 | 0.0395 (18) | 0.047 (2) | 0.0482 (18) | 0.0101 (15) | 0.0054 (15) | −0.0007 (17) |
C13 | 0.0413 (17) | 0.048 (2) | 0.0423 (19) | 0.0010 (17) | 0.0075 (15) | −0.0009 (17) |
C14 | 0.0439 (18) | 0.041 (2) | 0.0399 (18) | 0.0034 (16) | 0.0034 (15) | 0.0045 (15) |
C15 | 0.0419 (18) | 0.042 (2) | 0.049 (2) | 0.0084 (16) | 0.0040 (16) | 0.0017 (17) |
C16 | 0.0466 (19) | 0.053 (2) | 0.049 (2) | 0.0010 (17) | 0.0046 (16) | 0.0087 (17) |
C17 | 0.061 (2) | 0.097 (3) | 0.053 (2) | −0.001 (2) | −0.0028 (18) | 0.032 (2) |
C18 | 0.067 (3) | 0.131 (4) | 0.051 (2) | 0.017 (2) | 0.012 (2) | 0.033 (2) |
C19 | 0.065 (2) | 0.073 (3) | 0.056 (2) | 0.010 (2) | 0.0063 (19) | −0.004 (2) |
C20 | 0.056 (2) | 0.071 (2) | 0.046 (2) | −0.0046 (19) | 0.0064 (17) | −0.0034 (18) |
C21 | 0.076 (2) | 0.066 (2) | 0.080 (3) | 0.034 (2) | 0.013 (2) | 0.026 (2) |
C22 | 0.051 (2) | 0.079 (3) | 0.073 (2) | 0.012 (2) | 0.0230 (18) | −0.001 (2) |
Cl—C1 | 1.740 (3) | C9—C10 | 1.468 (3) |
O1—C19 | 1.411 (3) | C10—C11 | 1.413 (3) |
O1—C18 | 1.417 (3) | C10—C15 | 1.418 (3) |
O2—C9 | 1.253 (3) | C11—C12 | 1.385 (3) |
O3—C11 | 1.360 (3) | C12—C13 | 1.381 (3) |
O3—C21 | 1.426 (3) | C12—H12 | 0.9300 |
O4—C13 | 1.366 (3) | C13—C14 | 1.386 (3) |
O4—C22 | 1.427 (3) | C14—C15 | 1.390 (3) |
O5—C15 | 1.349 (3) | C14—C16 | 1.494 (3) |
O5—H0 | 0.90 (3) | C16—H16A | 0.9700 |
N—C20 | 1.447 (3) | C16—H16B | 0.9700 |
N—C17 | 1.466 (3) | C17—C18 | 1.498 (4) |
N—C16 | 1.469 (3) | C17—H17A | 0.9700 |
C1—C2 | 1.382 (4) | C17—H17B | 0.9700 |
C1—C6 | 1.393 (3) | C18—H18A | 0.9700 |
C2—C3 | 1.363 (4) | C18—H18B | 0.9700 |
C2—H2 | 0.9300 | C19—C20 | 1.499 (3) |
C3—C4 | 1.376 (4) | C19—H19A | 0.9700 |
C3—H3 | 0.9300 | C19—H19B | 0.9700 |
C4—C5 | 1.388 (4) | C20—H20A | 0.9700 |
C4—H4 | 0.9300 | C20—H20B | 0.9700 |
C5—C6 | 1.381 (4) | C21—H21A | 0.9600 |
C5—H5 | 0.9300 | C21—H21B | 0.9600 |
C6—C7 | 1.465 (4) | C21—H21C | 0.9600 |
C7—C8 | 1.309 (3) | C22—H22A | 0.9600 |
C7—H7 | 0.9300 | C22—H22B | 0.9600 |
C8—C9 | 1.472 (4) | C22—H22C | 0.9600 |
C8—H8 | 0.9300 | ||
C19—O1—C18 | 108.8 (2) | C13—C14—C16 | 120.3 (3) |
C11—O3—C21 | 119.7 (2) | C15—C14—C16 | 123.0 (3) |
C13—O4—C22 | 118.7 (2) | O5—C15—C14 | 115.9 (3) |
C15—O5—H0 | 107 (2) | O5—C15—C10 | 120.3 (2) |
C20—N—C17 | 107.9 (2) | C14—C15—C10 | 123.8 (3) |
C20—N—C16 | 112.1 (2) | N—C16—C14 | 112.2 (2) |
C17—N—C16 | 110.9 (2) | N—C16—H16A | 109.2 |
C2—C1—C6 | 121.8 (3) | C14—C16—H16A | 109.2 |
C2—C1—Cl | 117.3 (3) | N—C16—H16B | 109.2 |
C6—C1—Cl | 120.8 (3) | C14—C16—H16B | 109.2 |
C3—C2—C1 | 119.7 (3) | H16A—C16—H16B | 107.9 |
C3—C2—H2 | 120.1 | N—C17—C18 | 109.4 (3) |
C1—C2—H2 | 120.1 | N—C17—H17A | 109.8 |
C2—C3—C4 | 120.6 (4) | C18—C17—H17A | 109.8 |
C2—C3—H3 | 119.7 | N—C17—H17B | 109.8 |
C4—C3—H3 | 119.7 | C18—C17—H17B | 109.8 |
C3—C4—C5 | 118.9 (4) | H17A—C17—H17B | 108.2 |
C3—C4—H4 | 120.5 | O1—C18—C17 | 112.8 (3) |
C5—C4—H4 | 120.5 | O1—C18—H18A | 109.0 |
C6—C5—C4 | 122.3 (3) | C17—C18—H18A | 109.0 |
C6—C5—H5 | 118.8 | O1—C18—H18B | 109.0 |
C4—C5—H5 | 118.8 | C17—C18—H18B | 109.0 |
C5—C6—C1 | 116.6 (3) | H18A—C18—H18B | 107.8 |
C5—C6—C7 | 121.6 (3) | O1—C19—C20 | 112.6 (3) |
C1—C6—C7 | 121.9 (3) | O1—C19—H19A | 109.1 |
C8—C7—C6 | 126.1 (3) | C20—C19—H19A | 109.1 |
C8—C7—H7 | 116.9 | O1—C19—H19B | 109.1 |
C6—C7—H7 | 116.9 | C20—C19—H19B | 109.1 |
C7—C8—C9 | 122.4 (3) | H19A—C19—H19B | 107.8 |
C7—C8—H8 | 118.8 | N—C20—C19 | 111.0 (2) |
C9—C8—H8 | 118.8 | N—C20—H20A | 109.4 |
O2—C9—C10 | 119.5 (3) | C19—C20—H20A | 109.4 |
O2—C9—C8 | 117.4 (3) | N—C20—H20B | 109.4 |
C10—C9—C8 | 123.0 (3) | C19—C20—H20B | 109.4 |
C11—C10—C15 | 116.0 (2) | H20A—C20—H20B | 108.0 |
C11—C10—C9 | 125.4 (3) | O3—C21—H21A | 109.5 |
C15—C10—C9 | 118.6 (3) | O3—C21—H21B | 109.5 |
O3—C11—C12 | 120.9 (3) | H21A—C21—H21B | 109.5 |
O3—C11—C10 | 117.9 (2) | O3—C21—H21C | 109.5 |
C12—C11—C10 | 121.3 (3) | H21A—C21—H21C | 109.5 |
C13—C12—C11 | 119.6 (3) | H21B—C21—H21C | 109.5 |
C13—C12—H12 | 120.2 | O4—C22—H22A | 109.5 |
C11—C12—H12 | 120.2 | O4—C22—H22B | 109.5 |
O4—C13—C12 | 122.4 (3) | H22A—C22—H22B | 109.5 |
O4—C13—C14 | 115.0 (3) | O4—C22—H22C | 109.5 |
C12—C13—C14 | 122.6 (3) | H22A—C22—H22C | 109.5 |
C13—C14—C15 | 116.7 (3) | H22B—C22—H22C | 109.5 |
C6—C1—C2—C3 | 1.3 (5) | C22—O4—C13—C12 | −1.2 (4) |
Cl—C1—C2—C3 | 178.8 (3) | C22—O4—C13—C14 | 178.5 (2) |
C1—C2—C3—C4 | −0.5 (5) | C11—C12—C13—O4 | 179.4 (3) |
C2—C3—C4—C5 | 0.0 (5) | C11—C12—C13—C14 | −0.4 (4) |
C3—C4—C5—C6 | −0.3 (5) | O4—C13—C14—C15 | −177.1 (2) |
C4—C5—C6—C1 | 1.1 (5) | C12—C13—C14—C15 | 2.7 (4) |
C4—C5—C6—C7 | −179.5 (3) | O4—C13—C14—C16 | 0.4 (4) |
C2—C1—C6—C5 | −1.6 (4) | C12—C13—C14—C16 | −179.8 (3) |
Cl—C1—C6—C5 | −179.0 (2) | C13—C14—C15—O5 | 177.8 (2) |
C2—C1—C6—C7 | 179.0 (3) | C16—C14—C15—O5 | 0.4 (4) |
Cl—C1—C6—C7 | 1.6 (4) | C13—C14—C15—C10 | −2.9 (4) |
C5—C6—C7—C8 | 5.6 (5) | C16—C14—C15—C10 | 179.7 (3) |
C1—C6—C7—C8 | −175.1 (3) | C11—C10—C15—O5 | −179.9 (3) |
C6—C7—C8—C9 | 178.4 (3) | C9—C10—C15—O5 | −2.3 (4) |
C7—C8—C9—O2 | 4.5 (4) | C11—C10—C15—C14 | 0.8 (4) |
C7—C8—C9—C10 | −175.1 (3) | C9—C10—C15—C14 | 178.5 (3) |
O2—C9—C10—C11 | 173.6 (3) | C20—N—C16—C14 | 68.8 (3) |
C8—C9—C10—C11 | −6.8 (4) | C17—N—C16—C14 | −170.5 (2) |
O2—C9—C10—C15 | −3.9 (4) | C13—C14—C16—N | 80.9 (3) |
C8—C9—C10—C15 | 175.7 (3) | C15—C14—C16—N | −101.8 (3) |
C21—O3—C11—C12 | 5.4 (4) | C20—N—C17—C18 | −57.6 (3) |
C21—O3—C11—C10 | −174.4 (3) | C16—N—C17—C18 | 179.4 (2) |
C15—C10—C11—O3 | −178.6 (2) | C19—O1—C18—C17 | −57.4 (4) |
C9—C10—C11—O3 | 3.9 (4) | N—C17—C18—O1 | 59.6 (4) |
C15—C10—C11—C12 | 1.6 (4) | C18—O1—C19—C20 | 56.0 (3) |
C9—C10—C11—C12 | −175.9 (3) | C17—N—C20—C19 | 57.3 (3) |
O3—C11—C12—C13 | 178.4 (3) | C16—N—C20—C19 | 179.6 (2) |
C10—C11—C12—C13 | −1.8 (4) | O1—C19—C20—N | −58.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H0···O2 | 0.90 (3) | 1.62 (3) | 2.452 (3) | 152 (3) |
Experimental details
Crystal data | |
Chemical formula | C22H24ClNO5 |
Mr | 417.89 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.408 (2), 10.517 (2), 29.505 (6) |
β (°) | 92.90 (2) |
V (Å3) | 4154.9 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.60 × 0.50 × 0.12 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | ψ scan (SHELXTL; Bruker, 1997) |
Tmin, Tmax | 0.874, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4451, 3872, 1515 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.088, 0.81 |
No. of reflections | 3872 |
No. of parameters | 269 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: XSCANS (Bruker, 1997), XSCANS, SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL and PLATON (Spek, 2003), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H0···O2 | 0.90 (3) | 1.62 (3) | 2.452 (3) | 152 (3) |
Chalcones possess anti-inflammatory, antimalarial and antifertility activities, and are also reported as having antitumour activity (De Vincenzo et al., 1995; Christelle et al., 2001; Srinivas et al., 2003). With this in mind, a series of chalcones have been synthesized in our lab and have been evaluated for antitumor activity in vitro against various human tumor cell lines. Among them, the title compound has a broad antitumor spectrum and low micromolar IC50 ranging from 4.8 to 22.7 µmol L−1 against six human tumor cell lines. In order to obtain detailed information on its molecular conformation in the solid state, an X-ray structure determination of the title compound, (I), has been carried out.
The title molecule is illustrated in Fig. 1. The configuration of the carbonyl group with respect to the olefinic double bond is s-cis, which is the same as in two related structures (Ravishankar et al., 2003; Moorthi et al., 2005). The trans arrangement of the H atoms in the –CH═CH– group is consistent with the solution-phase 1H NMR studies (J = 15.6 Hz; Li & Su, 1994). The atoms in the unsaturated ketone group are essentially planar in accordance with the π-electron conjugation. The exocyclic angles around C10 deviate from the normal trigonal value of 120°, with a larger C11—C10—C9 angle of 125.4 (3)° and a smaller C15—C10—C9 angle of 118.6 (3)°. This may be the result of the intramolecular O—H···O hydrogen bond (Table 1). In the crystal structure, the only intermolecular interactions present are weak π stacking, where the central aromatic ring (C10–C15) and the p-chlorobezene ring (C1–C6), from pairs of molecules related by centers of symmetry, are separated by a centroid–centroid distance of 3.660 (2) Å and a perpendicular distance of 3.49 Å (Fig. 2).