3,5-Bis(arylidene)piperidin-4-one derivatives (BAPs) display good antitumour activity because of their double α,β-unsaturated ketone structural characteristics. Reported BAPs have generally been symmetric and asymmetric BAPs have been little documented. Three asymmetric BAPs, namely (5E)-3-(4-tert-butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one, C24H26FNO, (5), (5E)-3-(4-tert-butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one, C26H31NO3, (6), and (5E)-3-{3-[(E)-(2,3-dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one, C27H23FN2O3, (12), were generated by Claisen–Schmidt condensation. They are characterized by NMR and FT–IR spectroscopies, and elemental analysis. Single-crystal structure analysis reveals that the two arylidene rings on both sides of the BAP structures adopt an E stereochemistry of the olefinic double bonds and the compounds are E,E isomers. Molecules of (5) and (12) generate one-dimensional chains through intermolecular hydrogen bonds, while compound (6) generates a two-dimensional network through hydrogen bonds. Preliminary cytotoxicities toward human liver hepatocellular carcinoma cell line (HepG2), human acute mononuclear granulocyte leukaemia (THP-1) and human normal hepatical cell line (LO2) were evaluated.
Supporting information
CCDC references: 1823142; 1823143; 1823144
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
(5
E)-3-(4-
tert-Butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one (exp_2471)
top
Crystal data top
C24H26FNO | F(000) = 776 |
Mr = 363.46 | Dx = 1.168 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 13.4219 (4) Å | Cell parameters from 2876 reflections |
b = 8.3679 (3) Å | θ = 5.4–70.0° |
c = 18.5974 (7) Å | µ = 0.61 mm−1 |
β = 98.348 (3)° | T = 293 K |
V = 2066.60 (12) Å3 | Block, clear pale yellow |
Z = 4 | 0.52 × 0.40 × 0.24 mm |
Data collection top
SuperNova (Cu) X-ray Source diffractometer | 3891 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2903 reflections with I > 2σ(I) |
Detector resolution: 8.22 pixels mm-1 | Rint = 0.019 |
ω scans | θmax = 70.8°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −16→15 |
Tmin = 0.572, Tmax = 1.000 | k = −10→7 |
7470 measured reflections | l = −22→17 |
Refinement top
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0722P)2 + 0.1539P] where P = (Fo2 + 2Fc2)/3 |
3891 reflections | (Δ/σ)max < 0.001 |
279 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.01006 (13) | 0.0592 (2) | 0.17854 (9) | 0.0678 (4) | |
C2 | 0.11752 (14) | 0.0518 (2) | 0.16597 (10) | 0.0765 (5) | |
C3 | 0.19730 (13) | 0.0621 (2) | 0.23019 (9) | 0.0670 (4) | |
C4 | 0.16431 (13) | 0.0808 (2) | 0.30345 (9) | 0.0705 (5) | |
H4A | 0.2154 | 0.0371 | 0.3405 | 0.085* | |
H4B | 0.1566 | 0.1934 | 0.3137 | 0.085* | |
C5 | −0.01030 (13) | 0.0737 (2) | 0.25540 (10) | 0.0708 (5) | |
H5A | −0.0151 | 0.1857 | 0.2678 | 0.085* | |
H5B | −0.0742 | 0.0234 | 0.2599 | 0.085* | |
C6 | −0.06101 (14) | 0.0486 (2) | 0.12008 (10) | 0.0725 (5) | |
H6 | −0.0369 | 0.0347 | 0.0761 | 0.087* | |
C7 | −0.17038 (13) | 0.0558 (2) | 0.11504 (9) | 0.0672 (4) | |
C8 | −0.22864 (15) | −0.0255 (2) | 0.05828 (10) | 0.0773 (5) | |
H8 | −0.1969 | −0.0827 | 0.0252 | 0.093* | |
C9 | −0.33196 (15) | −0.0227 (3) | 0.05037 (11) | 0.0842 (6) | |
H9 | −0.3702 | −0.0785 | 0.0128 | 0.101* | |
C10 | −0.37731 (14) | 0.0637 (2) | 0.09868 (11) | 0.0793 (5) | |
C11 | −0.32444 (14) | 0.1479 (2) | 0.15435 (10) | 0.0809 (5) | |
H11 | −0.3574 | 0.2070 | 0.1861 | 0.097* | |
C12 | −0.22069 (14) | 0.1430 (2) | 0.16238 (10) | 0.0742 (5) | |
H12 | −0.1835 | 0.1993 | 0.2003 | 0.089* | |
C13 | 0.29299 (13) | 0.0472 (2) | 0.21867 (10) | 0.0694 (4) | |
H13 | 0.3013 | 0.0328 | 0.1703 | 0.083* | |
C14 | 0.38634 (12) | 0.04997 (19) | 0.26963 (9) | 0.0624 (4) | |
C15 | 0.46775 (13) | −0.0381 (2) | 0.25342 (10) | 0.0736 (5) | |
H15 | 0.4613 | −0.0956 | 0.2102 | 0.088* | |
C16 | 0.55769 (13) | −0.0427 (2) | 0.29938 (10) | 0.0737 (5) | |
H16 | 0.6096 | −0.1057 | 0.2869 | 0.088* | |
C17 | 0.57350 (12) | 0.04382 (19) | 0.36380 (9) | 0.0625 (4) | |
C18 | 0.49242 (13) | 0.1352 (2) | 0.37896 (10) | 0.0697 (4) | |
H18 | 0.4999 | 0.1964 | 0.4211 | 0.084* | |
C19 | 0.40119 (13) | 0.1383 (2) | 0.33365 (10) | 0.0704 (4) | |
H19 | 0.3489 | 0.2005 | 0.3462 | 0.084* | |
C20 | 0.04314 (15) | −0.0010 (3) | 0.37904 (11) | 0.0908 (6) | |
H20A | 0.0375 | 0.1072 | 0.3950 | 0.136* | |
H20B | 0.0947 | −0.0550 | 0.4112 | 0.136* | |
H20C | −0.0200 | −0.0550 | 0.3792 | 0.136* | |
C21 | 0.67402 (14) | 0.0415 (2) | 0.41374 (10) | 0.0720 (5) | |
C22 | 0.7442 (4) | −0.1001 (7) | 0.3991 (3) | 0.113 (2) | 0.562 (6) |
H22A | 0.7099 | −0.1995 | 0.4035 | 0.169* | 0.562 (6) |
H22B | 0.8045 | −0.0971 | 0.4338 | 0.169* | 0.562 (6) |
H22C | 0.7613 | −0.0908 | 0.3509 | 0.169* | 0.562 (6) |
C23 | 0.6581 (4) | 0.0238 (9) | 0.4940 (2) | 0.122 (3) | 0.562 (6) |
H23A | 0.6179 | 0.1111 | 0.5071 | 0.183* | 0.562 (6) |
H23B | 0.7222 | 0.0245 | 0.5246 | 0.183* | 0.562 (6) |
H23C | 0.6242 | −0.0752 | 0.5002 | 0.183* | 0.562 (6) |
C24 | 0.7321 (4) | 0.1956 (7) | 0.4047 (3) | 0.115 (2) | 0.562 (6) |
H24A | 0.7449 | 0.2042 | 0.3554 | 0.173* | 0.562 (6) |
H24B | 0.7949 | 0.1937 | 0.4368 | 0.173* | 0.562 (6) |
H24C | 0.6929 | 0.2856 | 0.4162 | 0.173* | 0.562 (6) |
C22' | 0.6850 (6) | −0.1217 (7) | 0.4461 (4) | 0.113 (3) | 0.438 (6) |
H22D | 0.7493 | −0.1306 | 0.4761 | 0.169* | 0.438 (6) |
H22E | 0.6804 | −0.1998 | 0.4080 | 0.169* | 0.438 (6) |
H22F | 0.6324 | −0.1398 | 0.4751 | 0.169* | 0.438 (6) |
C23' | 0.6760 (5) | 0.1680 (9) | 0.4721 (4) | 0.124 (3) | 0.438 (6) |
H23D | 0.6252 | 0.1448 | 0.5020 | 0.186* | 0.438 (6) |
H23E | 0.6630 | 0.2708 | 0.4498 | 0.186* | 0.438 (6) |
H23F | 0.7409 | 0.1688 | 0.5016 | 0.186* | 0.438 (6) |
C24' | 0.7554 (4) | 0.0798 (13) | 0.3666 (4) | 0.124 (3) | 0.438 (6) |
H24D | 0.8190 | 0.0935 | 0.3971 | 0.186* | 0.438 (6) |
H24E | 0.7381 | 0.1764 | 0.3398 | 0.186* | 0.438 (6) |
H24F | 0.7603 | −0.0066 | 0.3333 | 0.186* | 0.438 (6) |
F1 | −0.47961 (9) | 0.06919 (19) | 0.08984 (8) | 0.1122 (5) | |
N1 | 0.06919 (10) | −0.00149 (18) | 0.30561 (7) | 0.0680 (4) | |
O1 | 0.13921 (11) | 0.0391 (3) | 0.10479 (8) | 0.1166 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0702 (10) | 0.0645 (10) | 0.0675 (10) | 0.0039 (8) | 0.0059 (8) | −0.0006 (8) |
C2 | 0.0738 (11) | 0.0920 (14) | 0.0641 (10) | 0.0028 (9) | 0.0114 (8) | −0.0027 (9) |
C3 | 0.0661 (10) | 0.0688 (10) | 0.0668 (10) | −0.0023 (7) | 0.0126 (8) | −0.0011 (8) |
C4 | 0.0648 (10) | 0.0790 (11) | 0.0679 (10) | 0.0002 (8) | 0.0096 (8) | −0.0078 (8) |
C5 | 0.0649 (10) | 0.0748 (11) | 0.0714 (10) | 0.0056 (8) | 0.0057 (8) | −0.0018 (8) |
C6 | 0.0751 (11) | 0.0744 (11) | 0.0676 (10) | 0.0024 (8) | 0.0085 (8) | −0.0014 (8) |
C7 | 0.0735 (10) | 0.0643 (10) | 0.0612 (9) | 0.0002 (8) | 0.0017 (8) | 0.0032 (7) |
C8 | 0.0866 (12) | 0.0836 (12) | 0.0600 (10) | −0.0037 (9) | 0.0046 (9) | −0.0047 (9) |
C9 | 0.0826 (13) | 0.0947 (14) | 0.0709 (11) | −0.0155 (10) | −0.0041 (10) | −0.0031 (10) |
C10 | 0.0655 (10) | 0.0927 (14) | 0.0766 (12) | −0.0047 (9) | −0.0003 (9) | 0.0104 (10) |
C11 | 0.0775 (12) | 0.0861 (13) | 0.0764 (11) | 0.0087 (9) | 0.0025 (9) | −0.0064 (9) |
C12 | 0.0747 (11) | 0.0720 (11) | 0.0714 (10) | 0.0050 (8) | −0.0050 (8) | −0.0087 (8) |
C13 | 0.0717 (10) | 0.0734 (11) | 0.0649 (10) | −0.0043 (8) | 0.0161 (8) | −0.0018 (8) |
C14 | 0.0620 (9) | 0.0630 (10) | 0.0652 (9) | −0.0078 (7) | 0.0197 (7) | −0.0003 (7) |
C15 | 0.0696 (10) | 0.0863 (13) | 0.0684 (10) | −0.0067 (9) | 0.0225 (8) | −0.0176 (9) |
C16 | 0.0654 (10) | 0.0801 (12) | 0.0787 (11) | 0.0002 (8) | 0.0214 (9) | −0.0155 (9) |
C17 | 0.0660 (9) | 0.0590 (9) | 0.0653 (9) | −0.0078 (7) | 0.0190 (7) | −0.0005 (7) |
C18 | 0.0724 (10) | 0.0691 (10) | 0.0701 (10) | −0.0058 (8) | 0.0185 (8) | −0.0132 (8) |
C19 | 0.0673 (10) | 0.0678 (10) | 0.0793 (11) | −0.0006 (8) | 0.0210 (8) | −0.0128 (8) |
C20 | 0.0753 (12) | 0.1267 (17) | 0.0720 (12) | 0.0055 (11) | 0.0165 (10) | 0.0069 (12) |
C21 | 0.0706 (10) | 0.0719 (11) | 0.0739 (11) | −0.0027 (8) | 0.0117 (8) | −0.0016 (8) |
C22 | 0.084 (3) | 0.121 (4) | 0.127 (4) | 0.025 (3) | −0.005 (3) | −0.015 (3) |
C23 | 0.104 (3) | 0.190 (8) | 0.070 (2) | 0.026 (4) | 0.004 (2) | 0.020 (3) |
C24 | 0.095 (3) | 0.116 (4) | 0.125 (5) | −0.038 (3) | −0.015 (3) | 0.016 (3) |
C22' | 0.120 (5) | 0.093 (4) | 0.118 (5) | 0.013 (3) | −0.011 (4) | 0.016 (3) |
C23' | 0.112 (4) | 0.120 (6) | 0.124 (6) | 0.016 (4) | −0.037 (4) | −0.046 (5) |
C24' | 0.058 (3) | 0.198 (10) | 0.114 (5) | −0.023 (4) | 0.008 (3) | 0.005 (5) |
F1 | 0.0698 (7) | 0.1568 (13) | 0.1058 (9) | −0.0070 (7) | −0.0014 (6) | −0.0017 (8) |
N1 | 0.0606 (8) | 0.0799 (9) | 0.0633 (8) | 0.0042 (7) | 0.0088 (6) | 0.0036 (7) |
O1 | 0.0832 (10) | 0.201 (2) | 0.0664 (9) | 0.0037 (10) | 0.0137 (7) | −0.0094 (10) |
Geometric parameters (Å, º) top
C1—C6 | 1.341 (2) | C17—C18 | 1.392 (2) |
C1—C2 | 1.496 (3) | C17—C21 | 1.523 (2) |
C1—C5 | 1.499 (2) | C18—C19 | 1.382 (2) |
C2—O1 | 1.219 (2) | C18—H18 | 0.9300 |
C2—C3 | 1.486 (3) | C19—H19 | 0.9300 |
C3—C13 | 1.338 (2) | C20—N1 | 1.458 (2) |
C3—C4 | 1.501 (2) | C20—H20A | 0.9600 |
C4—N1 | 1.456 (2) | C20—H20B | 0.9600 |
C4—H4A | 0.9700 | C20—H20C | 0.9600 |
C4—H4B | 0.9700 | C21—C22' | 1.492 (6) |
C5—N1 | 1.455 (2) | C21—C23' | 1.514 (6) |
C5—H5A | 0.9700 | C21—C24 | 1.528 (5) |
C5—H5B | 0.9700 | C21—C24' | 1.531 (6) |
C6—C7 | 1.459 (3) | C21—C23 | 1.546 (5) |
C6—H6 | 0.9300 | C21—C22 | 1.562 (5) |
C7—C12 | 1.392 (2) | C22—H22A | 0.9600 |
C7—C8 | 1.396 (2) | C22—H22B | 0.9600 |
C8—C9 | 1.373 (3) | C22—H22C | 0.9600 |
C8—H8 | 0.9300 | C23—H23A | 0.9600 |
C9—C10 | 1.363 (3) | C23—H23B | 0.9600 |
C9—H9 | 0.9300 | C23—H23C | 0.9600 |
C10—F1 | 1.360 (2) | C24—H24A | 0.9600 |
C10—C11 | 1.363 (3) | C24—H24B | 0.9600 |
C11—C12 | 1.379 (3) | C24—H24C | 0.9600 |
C11—H11 | 0.9300 | C22'—H22D | 0.9600 |
C12—H12 | 0.9300 | C22'—H22E | 0.9600 |
C13—C14 | 1.457 (2) | C22'—H22F | 0.9600 |
C13—H13 | 0.9300 | C23'—H23D | 0.9600 |
C14—C15 | 1.387 (2) | C23'—H23E | 0.9600 |
C14—C19 | 1.391 (2) | C23'—H23F | 0.9600 |
C15—C16 | 1.375 (3) | C24'—H24D | 0.9600 |
C15—H15 | 0.9300 | C24'—H24E | 0.9600 |
C16—C17 | 1.389 (2) | C24'—H24F | 0.9600 |
C16—H16 | 0.9300 | | |
| | | |
C6—C1—C2 | 117.33 (17) | C18—C19—C14 | 121.06 (16) |
C6—C1—C5 | 124.88 (17) | C18—C19—H19 | 119.5 |
C2—C1—C5 | 117.78 (15) | C14—C19—H19 | 119.5 |
O1—C2—C3 | 120.87 (18) | N1—C20—H20A | 109.5 |
O1—C2—C1 | 121.06 (17) | N1—C20—H20B | 109.5 |
C3—C2—C1 | 118.07 (16) | H20A—C20—H20B | 109.5 |
C13—C3—C2 | 117.53 (17) | N1—C20—H20C | 109.5 |
C13—C3—C4 | 124.86 (16) | H20A—C20—H20C | 109.5 |
C2—C3—C4 | 117.55 (15) | H20B—C20—H20C | 109.5 |
N1—C4—C3 | 110.57 (14) | C22'—C21—C23' | 111.2 (4) |
N1—C4—H4A | 109.5 | C22'—C21—C17 | 106.5 (3) |
C3—C4—H4A | 109.5 | C23'—C21—C17 | 110.5 (3) |
N1—C4—H4B | 109.5 | C17—C21—C24 | 110.0 (2) |
C3—C4—H4B | 109.5 | C22'—C21—C24' | 112.7 (5) |
H4A—C4—H4B | 108.1 | C23'—C21—C24' | 109.0 (5) |
N1—C5—C1 | 111.03 (14) | C17—C21—C24' | 106.9 (3) |
N1—C5—H5A | 109.4 | C17—C21—C23 | 110.8 (2) |
C1—C5—H5A | 109.4 | C24—C21—C23 | 109.4 (4) |
N1—C5—H5B | 109.4 | C17—C21—C22 | 114.0 (2) |
C1—C5—H5B | 109.4 | C24—C21—C22 | 106.9 (4) |
H5A—C5—H5B | 108.0 | C23—C21—C22 | 105.5 (3) |
C1—C6—C7 | 129.80 (18) | C21—C22—H22A | 109.5 |
C1—C6—H6 | 115.1 | C21—C22—H22B | 109.5 |
C7—C6—H6 | 115.1 | H22A—C22—H22B | 109.5 |
C12—C7—C8 | 117.65 (17) | C21—C22—H22C | 109.5 |
C12—C7—C6 | 123.86 (16) | H22A—C22—H22C | 109.5 |
C8—C7—C6 | 118.46 (17) | H22B—C22—H22C | 109.5 |
C9—C8—C7 | 121.24 (19) | C21—C23—H23A | 109.5 |
C9—C8—H8 | 119.4 | C21—C23—H23B | 109.5 |
C7—C8—H8 | 119.4 | H23A—C23—H23B | 109.5 |
C10—C9—C8 | 118.62 (18) | C21—C23—H23C | 109.5 |
C10—C9—H9 | 120.7 | H23A—C23—H23C | 109.5 |
C8—C9—H9 | 120.7 | H23B—C23—H23C | 109.5 |
F1—C10—C11 | 118.65 (19) | C21—C24—H24A | 109.5 |
F1—C10—C9 | 118.54 (18) | C21—C24—H24B | 109.5 |
C11—C10—C9 | 122.79 (18) | H24A—C24—H24B | 109.5 |
C10—C11—C12 | 118.23 (19) | C21—C24—H24C | 109.5 |
C10—C11—H11 | 120.9 | H24A—C24—H24C | 109.5 |
C12—C11—H11 | 120.9 | H24B—C24—H24C | 109.5 |
C11—C12—C7 | 121.46 (17) | C21—C22'—H22D | 109.5 |
C11—C12—H12 | 119.3 | C21—C22'—H22E | 109.5 |
C7—C12—H12 | 119.3 | H22D—C22'—H22E | 109.5 |
C3—C13—C14 | 130.47 (17) | C21—C22'—H22F | 109.5 |
C3—C13—H13 | 114.8 | H22D—C22'—H22F | 109.5 |
C14—C13—H13 | 114.8 | H22E—C22'—H22F | 109.5 |
C15—C14—C19 | 116.68 (16) | C21—C23'—H23D | 109.5 |
C15—C14—C13 | 118.71 (16) | C21—C23'—H23E | 109.5 |
C19—C14—C13 | 124.60 (16) | H23D—C23'—H23E | 109.5 |
C16—C15—C14 | 121.89 (16) | C21—C23'—H23F | 109.5 |
C16—C15—H15 | 119.1 | H23D—C23'—H23F | 109.5 |
C14—C15—H15 | 119.1 | H23E—C23'—H23F | 109.5 |
C15—C16—C17 | 122.13 (17) | C21—C24'—H24D | 109.5 |
C15—C16—H16 | 118.9 | C21—C24'—H24E | 109.5 |
C17—C16—H16 | 118.9 | H24D—C24'—H24E | 109.5 |
C16—C17—C18 | 115.78 (16) | C21—C24'—H24F | 109.5 |
C16—C17—C21 | 122.02 (16) | H24D—C24'—H24F | 109.5 |
C18—C17—C21 | 122.19 (15) | H24E—C24'—H24F | 109.5 |
C19—C18—C17 | 122.44 (16) | C5—N1—C4 | 110.01 (15) |
C19—C18—H18 | 118.8 | C5—N1—C20 | 110.29 (14) |
C17—C18—H18 | 118.8 | C4—N1—C20 | 110.80 (14) |
| | | |
C6—C1—C2—O1 | 1.1 (3) | C3—C13—C14—C15 | 149.89 (19) |
C5—C1—C2—O1 | 179.6 (2) | C3—C13—C14—C19 | −31.6 (3) |
C6—C1—C2—C3 | −179.58 (16) | C19—C14—C15—C16 | 2.2 (3) |
C5—C1—C2—C3 | −1.0 (2) | C13—C14—C15—C16 | −179.16 (17) |
O1—C2—C3—C13 | −4.0 (3) | C14—C15—C16—C17 | −1.8 (3) |
C1—C2—C3—C13 | 176.69 (16) | C15—C16—C17—C18 | 0.1 (3) |
O1—C2—C3—C4 | 178.8 (2) | C15—C16—C17—C21 | −178.55 (17) |
C1—C2—C3—C4 | −0.5 (2) | C16—C17—C18—C19 | 1.0 (3) |
C13—C3—C4—N1 | −144.49 (17) | C21—C17—C18—C19 | 179.67 (16) |
C2—C3—C4—N1 | 32.5 (2) | C17—C18—C19—C14 | −0.5 (3) |
C6—C1—C5—N1 | 148.92 (18) | C15—C14—C19—C18 | −1.1 (3) |
C2—C1—C5—N1 | −29.5 (2) | C13—C14—C19—C18 | −179.62 (16) |
C2—C1—C6—C7 | −178.40 (17) | C16—C17—C21—C22' | −69.4 (4) |
C5—C1—C6—C7 | 3.2 (3) | C18—C17—C21—C22' | 112.0 (4) |
C1—C6—C7—C12 | 30.3 (3) | C16—C17—C21—C23' | 169.8 (4) |
C1—C6—C7—C8 | −151.62 (19) | C18—C17—C21—C23' | −8.8 (5) |
C12—C7—C8—C9 | −1.5 (3) | C16—C17—C21—C24 | 103.0 (4) |
C6—C7—C8—C9 | −179.66 (18) | C18—C17—C21—C24 | −75.6 (4) |
C7—C8—C9—C10 | 1.0 (3) | C16—C17—C21—C24' | 51.3 (5) |
C8—C9—C10—F1 | 178.59 (18) | C18—C17—C21—C24' | −127.3 (5) |
C8—C9—C10—C11 | 0.3 (3) | C16—C17—C21—C23 | −135.9 (3) |
F1—C10—C11—C12 | −179.27 (17) | C18—C17—C21—C23 | 45.5 (4) |
C9—C10—C11—C12 | −1.0 (3) | C16—C17—C21—C22 | −17.1 (4) |
C10—C11—C12—C7 | 0.4 (3) | C18—C17—C21—C22 | 164.3 (3) |
C8—C7—C12—C11 | 0.8 (3) | C1—C5—N1—C4 | 63.39 (19) |
C6—C7—C12—C11 | 178.85 (17) | C1—C5—N1—C20 | −174.09 (16) |
C2—C3—C13—C14 | −179.20 (17) | C3—C4—N1—C5 | −64.96 (19) |
C4—C3—C13—C14 | −2.2 (3) | C3—C4—N1—C20 | 172.82 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.67 | 3.422 (2) | 139 |
C15—H15···F1ii | 0.93 | 2.84 | 3.344 (2) | 115 |
C9—H9···F1iii | 0.93 | 2.57 | 3.381 (2) | 146 |
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) −x−1, −y, −z. |
(5
E)-3-(4-
tert-Butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one (exp_2473)
top
Crystal data top
C26H31NO3 | F(000) = 872 |
Mr = 405.52 | Dx = 1.157 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 19.1378 (9) Å | Cell parameters from 3159 reflections |
b = 16.2788 (8) Å | θ = 4.7–70.3° |
c = 7.5525 (4) Å | µ = 0.59 mm−1 |
β = 98.386 (5)° | T = 293 K |
V = 2327.8 (2) Å3 | Block, clear pale yellow |
Z = 4 | 0.52 × 0.40 × 0.24 mm |
Data collection top
SuperNova (Cu) X-ray Source diffractometer | 4384 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3392 reflections with I > 2σ(I) |
Detector resolution: 8.22 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 71.1°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −23→20 |
Tmin = 0.656, Tmax = 1.000 | k = −18→19 |
8937 measured reflections | l = −6→9 |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0701P)2 + 0.2988P] where P = (Fo2 + 2Fc2)/3 |
4384 reflections | (Δ/σ)max = 0.002 |
317 parameters | Δρmax = 0.17 e Å−3 |
6 restraints | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 1.10312 (8) | 0.74376 (10) | 0.5015 (2) | 0.0518 (4) | |
C2 | 1.05524 (8) | 0.67263 (10) | 0.4555 (2) | 0.0532 (4) | |
C3 | 0.97825 (8) | 0.68992 (9) | 0.40452 (19) | 0.0479 (3) | |
C4 | 0.95536 (8) | 0.77779 (9) | 0.3912 (2) | 0.0505 (4) | |
H4A | 0.9126 | 0.7826 | 0.3055 | 0.061* | |
H4B | 0.9448 | 0.7962 | 0.5066 | 0.061* | |
C5 | 1.07319 (8) | 0.82826 (10) | 0.4694 (2) | 0.0551 (4) | |
H5A | 1.0617 | 0.8501 | 0.5811 | 0.066* | |
H5B | 1.1087 | 0.8636 | 0.4302 | 0.066* | |
C6 | 1.17117 (8) | 0.72718 (11) | 0.5650 (2) | 0.0591 (4) | |
H6 | 1.1824 | 0.6717 | 0.5776 | 0.071* | |
C7 | 1.23003 (8) | 0.78401 (11) | 0.6171 (2) | 0.0586 (4) | |
C8 | 1.29785 (8) | 0.75479 (12) | 0.6092 (2) | 0.0639 (4) | |
H8 | 1.3044 | 0.7007 | 0.5755 | 0.077* | |
C9 | 1.35546 (9) | 0.80611 (12) | 0.6515 (3) | 0.0681 (5) | |
C10 | 1.34641 (9) | 0.88608 (12) | 0.7031 (3) | 0.0715 (5) | |
H10 | 1.3853 | 0.9205 | 0.7301 | 0.086* | |
C11 | 1.27954 (9) | 0.91491 (12) | 0.7144 (2) | 0.0666 (5) | |
C12 | 1.22146 (9) | 0.86452 (12) | 0.6731 (2) | 0.0631 (4) | |
H12 | 1.1766 | 0.8843 | 0.6828 | 0.076* | |
C13 | 0.93464 (8) | 0.62534 (10) | 0.3737 (2) | 0.0515 (4) | |
H13 | 0.9569 | 0.5744 | 0.3795 | 0.062* | |
C14 | 0.85744 (8) | 0.62236 (9) | 0.3324 (2) | 0.0521 (4) | |
C15 | 0.82628 (9) | 0.55118 (11) | 0.2573 (3) | 0.0688 (5) | |
H15 | 0.8549 | 0.5081 | 0.2309 | 0.083* | |
C16 | 0.75383 (10) | 0.54255 (12) | 0.2206 (3) | 0.0787 (6) | |
H16 | 0.7351 | 0.4942 | 0.1680 | 0.094* | |
C17 | 0.70863 (9) | 0.60341 (11) | 0.2595 (3) | 0.0658 (5) | |
C18 | 0.73948 (9) | 0.67383 (11) | 0.3373 (3) | 0.0714 (5) | |
H18 | 0.7105 | 0.7162 | 0.3661 | 0.086* | |
C19 | 0.81192 (9) | 0.68365 (10) | 0.3739 (3) | 0.0652 (5) | |
H19 | 0.8305 | 0.7320 | 0.4272 | 0.078* | |
C20 | 1.44015 (11) | 0.69923 (15) | 0.6464 (4) | 0.0986 (8) | |
H20A | 1.4244 | 0.6734 | 0.7477 | 0.148* | |
H20B | 1.4903 | 0.6921 | 0.6529 | 0.148* | |
H20C | 1.4167 | 0.6746 | 0.5382 | 0.148* | |
C21 | 1.20856 (12) | 1.02983 (15) | 0.7716 (4) | 0.0999 (8) | |
H21A | 1.1814 | 1.0251 | 0.6547 | 0.150* | |
H21B | 1.2137 | 1.0868 | 0.8039 | 0.150* | |
H21C | 1.1848 | 1.0015 | 0.8570 | 0.150* | |
C22 | 0.98409 (10) | 0.91333 (10) | 0.3108 (3) | 0.0656 (5) | |
H22A | 0.9421 | 0.9139 | 0.2239 | 0.098* | |
H22B | 1.0196 | 0.9471 | 0.2696 | 0.098* | |
H22C | 0.9734 | 0.9343 | 0.4226 | 0.098* | |
C23 | 0.6324 (9) | 0.5969 (8) | 0.2341 (17) | 0.077 (6) | 0.314 (17) |
C24 | 0.6033 (10) | 0.5143 (14) | 0.163 (6) | 0.224 (16) | 0.314 (17) |
H24A | 0.6232 | 0.5004 | 0.0572 | 0.336* | 0.314 (17) |
H24B | 0.5528 | 0.5177 | 0.1339 | 0.336* | 0.314 (17) |
H24C | 0.6155 | 0.4728 | 0.2523 | 0.336* | 0.314 (17) |
C25 | 0.6002 (7) | 0.6620 (19) | 0.099 (4) | 0.154 (9) | 0.314 (17) |
H25A | 0.6128 | 0.7158 | 0.1452 | 0.231* | 0.314 (17) |
H25B | 0.5497 | 0.6565 | 0.0801 | 0.231* | 0.314 (17) |
H25C | 0.6180 | 0.6544 | −0.0122 | 0.231* | 0.314 (17) |
C26 | 0.5908 (9) | 0.6165 (15) | 0.386 (2) | 0.139 (7) | 0.314 (17) |
H26A | 0.6026 | 0.5776 | 0.4809 | 0.208* | 0.314 (17) |
H26B | 0.5411 | 0.6132 | 0.3423 | 0.208* | 0.314 (17) |
H26C | 0.6022 | 0.6709 | 0.4293 | 0.208* | 0.314 (17) |
C23A | 0.6267 (4) | 0.5914 (4) | 0.2172 (12) | 0.090 (3) | 0.686 (17) |
C24A | 0.6088 (4) | 0.5030 (5) | 0.2497 (13) | 0.130 (3) | 0.686 (17) |
H24D | 0.5585 | 0.4964 | 0.2338 | 0.195* | 0.686 (17) |
H24E | 0.6283 | 0.4878 | 0.3696 | 0.195* | 0.686 (17) |
H24F | 0.6284 | 0.4684 | 0.1663 | 0.195* | 0.686 (17) |
C25A | 0.6040 (4) | 0.6108 (7) | 0.0215 (13) | 0.143 (3) | 0.686 (17) |
H25D | 0.5547 | 0.5987 | −0.0104 | 0.215* | 0.686 (17) |
H25E | 0.6310 | 0.5781 | −0.0500 | 0.215* | 0.686 (17) |
H25F | 0.6121 | 0.6680 | 0.0006 | 0.215* | 0.686 (17) |
C26A | 0.5939 (4) | 0.6470 (10) | 0.344 (2) | 0.228 (8) | 0.686 (17) |
H26D | 0.6063 | 0.7030 | 0.3242 | 0.342* | 0.686 (17) |
H26E | 0.6112 | 0.6319 | 0.4654 | 0.342* | 0.686 (17) |
H26F | 0.5435 | 0.6412 | 0.3226 | 0.342* | 0.686 (17) |
N1 | 1.00996 (7) | 0.82979 (8) | 0.33549 (17) | 0.0515 (3) | |
O1 | 1.07785 (6) | 0.60222 (7) | 0.45855 (19) | 0.0718 (4) | |
O2 | 1.42411 (7) | 0.78390 (10) | 0.6466 (3) | 0.0979 (5) | |
O3 | 1.27653 (7) | 0.99442 (9) | 0.7703 (2) | 0.0933 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0411 (8) | 0.0655 (9) | 0.0492 (8) | −0.0034 (7) | 0.0079 (6) | −0.0024 (7) |
C2 | 0.0438 (8) | 0.0629 (9) | 0.0538 (9) | −0.0003 (7) | 0.0094 (6) | −0.0031 (7) |
C3 | 0.0429 (8) | 0.0575 (9) | 0.0434 (8) | −0.0004 (6) | 0.0066 (6) | −0.0035 (6) |
C4 | 0.0418 (8) | 0.0583 (9) | 0.0511 (8) | −0.0021 (7) | 0.0054 (6) | −0.0035 (7) |
C5 | 0.0453 (8) | 0.0635 (10) | 0.0560 (9) | −0.0084 (7) | 0.0059 (7) | −0.0040 (7) |
C6 | 0.0465 (9) | 0.0731 (11) | 0.0575 (9) | −0.0015 (8) | 0.0071 (7) | −0.0004 (8) |
C7 | 0.0407 (8) | 0.0782 (11) | 0.0560 (9) | −0.0041 (8) | 0.0039 (6) | 0.0007 (8) |
C8 | 0.0441 (9) | 0.0755 (11) | 0.0711 (11) | −0.0013 (8) | 0.0056 (7) | −0.0028 (9) |
C9 | 0.0388 (9) | 0.0846 (13) | 0.0805 (12) | −0.0011 (8) | 0.0071 (8) | 0.0036 (10) |
C10 | 0.0464 (9) | 0.0814 (13) | 0.0840 (13) | −0.0102 (9) | 0.0007 (8) | 0.0000 (10) |
C11 | 0.0540 (10) | 0.0757 (12) | 0.0677 (11) | −0.0029 (8) | 0.0013 (8) | −0.0074 (9) |
C12 | 0.0420 (9) | 0.0841 (12) | 0.0622 (10) | −0.0013 (8) | 0.0044 (7) | −0.0076 (9) |
C13 | 0.0457 (8) | 0.0553 (9) | 0.0527 (8) | 0.0024 (7) | 0.0042 (6) | −0.0056 (7) |
C14 | 0.0447 (8) | 0.0530 (9) | 0.0571 (9) | −0.0003 (6) | 0.0024 (6) | −0.0028 (7) |
C15 | 0.0501 (9) | 0.0599 (10) | 0.0944 (13) | 0.0019 (8) | 0.0034 (9) | −0.0199 (9) |
C16 | 0.0512 (10) | 0.0698 (11) | 0.1102 (16) | −0.0048 (9) | −0.0045 (10) | −0.0303 (11) |
C17 | 0.0440 (10) | 0.0650 (10) | 0.0848 (12) | −0.0016 (8) | −0.0022 (8) | −0.0012 (9) |
C18 | 0.0481 (10) | 0.0564 (10) | 0.1098 (15) | 0.0052 (8) | 0.0111 (9) | −0.0021 (10) |
C19 | 0.0500 (10) | 0.0540 (9) | 0.0919 (13) | −0.0034 (7) | 0.0113 (9) | −0.0105 (8) |
C20 | 0.0537 (12) | 0.1033 (17) | 0.136 (2) | 0.0129 (11) | 0.0036 (12) | −0.0175 (15) |
C21 | 0.0817 (15) | 0.1014 (17) | 0.1140 (18) | 0.0132 (13) | 0.0055 (13) | −0.0379 (14) |
C22 | 0.0647 (11) | 0.0579 (10) | 0.0733 (11) | −0.0013 (8) | 0.0073 (8) | −0.0004 (8) |
C23 | 0.073 (11) | 0.074 (8) | 0.080 (7) | −0.014 (6) | −0.006 (6) | 0.006 (6) |
C24 | 0.061 (7) | 0.147 (16) | 0.45 (4) | −0.015 (9) | −0.011 (16) | −0.18 (2) |
C25 | 0.047 (5) | 0.22 (2) | 0.188 (17) | 0.019 (10) | −0.015 (7) | 0.060 (15) |
C26 | 0.084 (9) | 0.219 (19) | 0.123 (10) | −0.061 (9) | 0.050 (7) | −0.055 (9) |
C23A | 0.030 (3) | 0.090 (5) | 0.142 (6) | 0.003 (2) | −0.014 (3) | −0.017 (4) |
C24A | 0.053 (3) | 0.128 (5) | 0.205 (6) | −0.025 (3) | 0.006 (3) | 0.040 (5) |
C25A | 0.088 (4) | 0.147 (6) | 0.171 (7) | −0.024 (4) | −0.059 (4) | 0.040 (4) |
C26A | 0.042 (3) | 0.241 (12) | 0.408 (19) | −0.021 (4) | 0.054 (6) | −0.188 (12) |
N1 | 0.0468 (7) | 0.0547 (7) | 0.0524 (7) | −0.0020 (6) | 0.0054 (5) | 0.0013 (6) |
O1 | 0.0477 (7) | 0.0630 (7) | 0.1038 (10) | 0.0065 (6) | 0.0081 (6) | −0.0083 (6) |
O2 | 0.0398 (7) | 0.0966 (11) | 0.1572 (15) | 0.0006 (7) | 0.0143 (8) | −0.0054 (10) |
O3 | 0.0654 (9) | 0.0876 (10) | 0.1213 (12) | −0.0021 (7) | −0.0049 (8) | −0.0322 (9) |
Geometric parameters (Å, º) top
C1—C6 | 1.348 (2) | C18—H18 | 0.9300 |
C1—C2 | 1.486 (2) | C19—H19 | 0.9300 |
C1—C5 | 1.496 (2) | C20—O2 | 1.412 (3) |
C2—O1 | 1.2242 (18) | C20—H20A | 0.9600 |
C2—C3 | 1.494 (2) | C20—H20B | 0.9600 |
C3—C13 | 1.341 (2) | C20—H20C | 0.9600 |
C3—C4 | 1.495 (2) | C21—O3 | 1.424 (2) |
C4—N1 | 1.4538 (18) | C21—H21A | 0.9600 |
C4—H4A | 0.9700 | C21—H21B | 0.9600 |
C4—H4B | 0.9700 | C21—H21C | 0.9600 |
C5—N1 | 1.460 (2) | C22—N1 | 1.450 (2) |
C5—H5A | 0.9700 | C22—H22A | 0.9600 |
C5—H5B | 0.9700 | C22—H22B | 0.9600 |
C6—C7 | 1.466 (2) | C22—H22C | 0.9600 |
C6—H6 | 0.9300 | C23—C26 | 1.521 (9) |
C7—C8 | 1.392 (2) | C23—C24 | 1.524 (9) |
C7—C12 | 1.394 (2) | C23—C25 | 1.536 (9) |
C8—C9 | 1.383 (2) | C24—H24A | 0.9600 |
C8—H8 | 0.9300 | C24—H24B | 0.9600 |
C9—O2 | 1.368 (2) | C24—H24C | 0.9600 |
C9—C10 | 1.377 (3) | C25—H25A | 0.9600 |
C10—C11 | 1.378 (3) | C25—H25B | 0.9600 |
C10—H10 | 0.9300 | C25—H25C | 0.9600 |
C11—O3 | 1.365 (2) | C26—H26A | 0.9600 |
C11—C12 | 1.380 (2) | C26—H26B | 0.9600 |
C12—H12 | 0.9300 | C26—H26C | 0.9600 |
C13—C14 | 1.466 (2) | C23A—C24A | 1.508 (7) |
C13—H13 | 0.9300 | C23A—C25A | 1.512 (7) |
C14—C15 | 1.386 (2) | C23A—C26A | 1.518 (7) |
C14—C19 | 1.390 (2) | C24A—H24D | 0.9600 |
C15—C16 | 1.381 (2) | C24A—H24E | 0.9600 |
C15—H15 | 0.9300 | C24A—H24F | 0.9600 |
C16—C17 | 1.375 (3) | C25A—H25D | 0.9600 |
C16—H16 | 0.9300 | C25A—H25E | 0.9600 |
C17—C18 | 1.381 (2) | C25A—H25F | 0.9600 |
C17—C23 | 1.447 (17) | C26A—H26D | 0.9600 |
C17—C23A | 1.566 (8) | C26A—H26E | 0.9600 |
C18—C19 | 1.383 (2) | C26A—H26F | 0.9600 |
| | | |
C6—C1—C2 | 117.26 (15) | O2—C20—H20C | 109.5 |
C6—C1—C5 | 124.67 (15) | H20A—C20—H20C | 109.5 |
C2—C1—C5 | 118.04 (13) | H20B—C20—H20C | 109.5 |
O1—C2—C1 | 121.40 (14) | O3—C21—H21A | 109.5 |
O1—C2—C3 | 120.91 (14) | O3—C21—H21B | 109.5 |
C1—C2—C3 | 117.69 (14) | H21A—C21—H21B | 109.5 |
C13—C3—C2 | 117.53 (14) | O3—C21—H21C | 109.5 |
C13—C3—C4 | 124.71 (14) | H21A—C21—H21C | 109.5 |
C2—C3—C4 | 117.75 (13) | H21B—C21—H21C | 109.5 |
N1—C4—C3 | 111.15 (12) | N1—C22—H22A | 109.5 |
N1—C4—H4A | 109.4 | N1—C22—H22B | 109.5 |
C3—C4—H4A | 109.4 | H22A—C22—H22B | 109.5 |
N1—C4—H4B | 109.4 | N1—C22—H22C | 109.5 |
C3—C4—H4B | 109.4 | H22A—C22—H22C | 109.5 |
H4A—C4—H4B | 108.0 | H22B—C22—H22C | 109.5 |
N1—C5—C1 | 112.77 (13) | C17—C23—C26 | 120.9 (12) |
N1—C5—H5A | 109.0 | C17—C23—C24 | 114.9 (12) |
C1—C5—H5A | 109.0 | C26—C23—C24 | 104.2 (16) |
N1—C5—H5B | 109.0 | C17—C23—C25 | 109.7 (9) |
C1—C5—H5B | 109.0 | C26—C23—C25 | 98.7 (15) |
H5A—C5—H5B | 107.8 | C24—C23—C25 | 106.5 (15) |
C1—C6—C7 | 129.33 (17) | C23—C24—H24A | 109.5 |
C1—C6—H6 | 115.3 | C23—C24—H24B | 109.5 |
C7—C6—H6 | 115.3 | H24A—C24—H24B | 109.5 |
C8—C7—C12 | 119.08 (16) | C23—C24—H24C | 109.5 |
C8—C7—C6 | 117.23 (16) | H24A—C24—H24C | 109.5 |
C12—C7—C6 | 123.68 (15) | H24B—C24—H24C | 109.5 |
C9—C8—C7 | 120.04 (18) | C23—C25—H25A | 109.5 |
C9—C8—H8 | 120.0 | C23—C25—H25B | 109.5 |
C7—C8—H8 | 120.0 | H25A—C25—H25B | 109.5 |
O2—C9—C10 | 114.72 (16) | C23—C25—H25C | 109.5 |
O2—C9—C8 | 124.78 (18) | H25A—C25—H25C | 109.5 |
C10—C9—C8 | 120.50 (17) | H25B—C25—H25C | 109.5 |
C9—C10—C11 | 119.73 (17) | C23—C26—H26A | 109.5 |
C9—C10—H10 | 120.1 | C23—C26—H26B | 109.5 |
C11—C10—H10 | 120.1 | H26A—C26—H26B | 109.5 |
O3—C11—C10 | 115.06 (17) | C23—C26—H26C | 109.5 |
O3—C11—C12 | 124.36 (17) | H26A—C26—H26C | 109.5 |
C10—C11—C12 | 120.57 (18) | H26B—C26—H26C | 109.5 |
C11—C12—C7 | 120.04 (16) | C24A—C23A—C25A | 108.6 (6) |
C11—C12—H12 | 120.0 | C24A—C23A—C26A | 110.0 (9) |
C7—C12—H12 | 120.0 | C25A—C23A—C26A | 114.0 (7) |
C3—C13—C14 | 130.18 (15) | C24A—C23A—C17 | 109.3 (5) |
C3—C13—H13 | 114.9 | C25A—C23A—C17 | 108.0 (5) |
C14—C13—H13 | 114.9 | C26A—C23A—C17 | 106.9 (6) |
C15—C14—C19 | 116.48 (15) | C23A—C24A—H24D | 109.5 |
C15—C14—C13 | 118.36 (14) | C23A—C24A—H24E | 109.5 |
C19—C14—C13 | 125.00 (14) | H24D—C24A—H24E | 109.5 |
C16—C15—C14 | 121.78 (16) | C23A—C24A—H24F | 109.5 |
C16—C15—H15 | 119.1 | H24D—C24A—H24F | 109.5 |
C14—C15—H15 | 119.1 | H24E—C24A—H24F | 109.5 |
C17—C16—C15 | 121.89 (17) | C23A—C25A—H25D | 109.5 |
C17—C16—H16 | 119.1 | C23A—C25A—H25E | 109.5 |
C15—C16—H16 | 119.1 | H25D—C25A—H25E | 109.5 |
C16—C17—C18 | 116.49 (16) | C23A—C25A—H25F | 109.5 |
C16—C17—C23 | 124.9 (6) | H25D—C25A—H25F | 109.5 |
C18—C17—C23 | 118.5 (6) | H25E—C25A—H25F | 109.5 |
C16—C17—C23A | 120.6 (3) | C23A—C26A—H26D | 109.5 |
C18—C17—C23A | 122.9 (3) | C23A—C26A—H26E | 109.5 |
C17—C18—C19 | 122.34 (17) | H26D—C26A—H26E | 109.5 |
C17—C18—H18 | 118.8 | C23A—C26A—H26F | 109.5 |
C19—C18—H18 | 118.8 | H26D—C26A—H26F | 109.5 |
C18—C19—C14 | 120.99 (16) | H26E—C26A—H26F | 109.5 |
C18—C19—H19 | 119.5 | C22—N1—C4 | 109.69 (13) |
C14—C19—H19 | 119.5 | C22—N1—C5 | 109.76 (13) |
O2—C20—H20A | 109.5 | C4—N1—C5 | 110.35 (12) |
O2—C20—H20B | 109.5 | C9—O2—C20 | 117.88 (16) |
H20A—C20—H20B | 109.5 | C11—O3—C21 | 117.76 (16) |
| | | |
C6—C1—C2—O1 | −6.9 (2) | C19—C14—C15—C16 | 1.9 (3) |
C5—C1—C2—O1 | 171.41 (15) | C13—C14—C15—C16 | 177.61 (18) |
C6—C1—C2—C3 | 173.30 (14) | C14—C15—C16—C17 | −1.2 (3) |
C5—C1—C2—C3 | −8.4 (2) | C15—C16—C17—C18 | 0.0 (3) |
O1—C2—C3—C13 | 4.1 (2) | C15—C16—C17—C23 | −176.4 (6) |
C1—C2—C3—C13 | −176.02 (13) | C15—C16—C17—C23A | −179.6 (4) |
O1—C2—C3—C4 | −175.73 (14) | C16—C17—C18—C19 | 0.4 (3) |
C1—C2—C3—C4 | 4.1 (2) | C23—C17—C18—C19 | 177.0 (6) |
C13—C3—C4—N1 | −148.83 (14) | C23A—C17—C18—C19 | 180.0 (4) |
C2—C3—C4—N1 | 31.04 (18) | C17—C18—C19—C14 | 0.4 (3) |
C6—C1—C5—N1 | 155.52 (15) | C15—C14—C19—C18 | −1.5 (3) |
C2—C1—C5—N1 | −22.62 (19) | C13—C14—C19—C18 | −176.88 (17) |
C2—C1—C6—C7 | 178.52 (15) | C16—C17—C23—C26 | 128.0 (14) |
C5—C1—C6—C7 | 0.4 (3) | C18—C17—C23—C26 | −48.4 (16) |
C1—C6—C7—C8 | −154.72 (17) | C16—C17—C23—C24 | 2 (2) |
C1—C6—C7—C12 | 25.3 (3) | C18—C17—C23—C24 | −174.8 (19) |
C12—C7—C8—C9 | −1.9 (3) | C16—C17—C23—C25 | −118.3 (16) |
C6—C7—C8—C9 | 178.09 (16) | C18—C17—C23—C25 | 65.3 (18) |
C7—C8—C9—O2 | −179.37 (18) | C16—C17—C23A—C24A | 36.1 (8) |
C7—C8—C9—C10 | 0.5 (3) | C18—C17—C23A—C24A | −143.5 (5) |
O2—C9—C10—C11 | −179.39 (18) | C16—C17—C23A—C25A | −81.9 (7) |
C8—C9—C10—C11 | 0.7 (3) | C18—C17—C23A—C25A | 98.5 (6) |
C9—C10—C11—O3 | 178.68 (17) | C16—C17—C23A—C26A | 155.1 (9) |
C9—C10—C11—C12 | −0.5 (3) | C18—C17—C23A—C26A | −24.5 (9) |
O3—C11—C12—C7 | 179.98 (17) | C3—C4—N1—C22 | 175.71 (13) |
C10—C11—C12—C7 | −0.9 (3) | C3—C4—N1—C5 | −63.25 (16) |
C8—C7—C12—C11 | 2.1 (3) | C1—C5—N1—C22 | −179.78 (13) |
C6—C7—C12—C11 | −177.91 (16) | C1—C5—N1—C4 | 59.22 (17) |
C2—C3—C13—C14 | 176.06 (15) | C10—C9—O2—C20 | 162.1 (2) |
C4—C3—C13—C14 | −4.1 (3) | C8—C9—O2—C20 | −18.0 (3) |
C3—C13—C14—C15 | 162.00 (17) | C10—C11—O3—C21 | 175.3 (2) |
C3—C13—C14—C19 | −22.7 (3) | C12—C11—O3—C21 | −5.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C26A—H26F···O2i | 0.96 | 2.75 | 3.554 (12) | 141 |
C22—H22B···O1ii | 0.96 | 2.86 | 3.429 (2) | 119 |
Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, −y+3/2, z−1/2. |
(5
E)-3-{3-[(
E)-(2,3-Dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one (exp_2476)
top
Crystal data top
C27H23FN2O3 | Z = 2 |
Mr = 442.47 | F(000) = 464 |
Triclinic, P1 | Dx = 1.334 Mg m−3 |
a = 7.0689 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.2072 (5) Å | Cell parameters from 2081 reflections |
c = 20.1397 (16) Å | θ = 7.5–69.2° |
α = 94.401 (6)° | µ = 0.76 mm−1 |
β = 97.829 (6)° | T = 293 K |
γ = 106.575 (6)° | Plate, clear light bronze |
V = 1101.18 (14) Å3 | 0.20 × 0.10 × 0.02 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Eos detector | 4126 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2886 reflections with I > 2σ(I) |
Detector resolution: 8.22 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 71.0°, θmin = 4.5° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −8→8 |
Tmin = 0.917, Tmax = 1.000 | k = −9→6 |
7150 measured reflections | l = −19→24 |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0733P)2 + 0.0127P] where P = (Fo2 + 2Fc2)/3 |
4126 reflections | (Δ/σ)max = 0.001 |
301 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2270 (3) | 0.2496 (3) | 0.76231 (10) | 0.0560 (5) | |
C2 | 0.2252 (3) | 0.1517 (3) | 0.69695 (10) | 0.0574 (5) | |
C3 | 0.4174 (3) | 0.1906 (3) | 0.66868 (11) | 0.0621 (5) | |
H3A | 0.4945 | 0.1171 | 0.6851 | 0.075* | |
H3B | 0.3878 | 0.1681 | 0.6198 | 0.075* | |
C4 | 0.5997 (3) | 0.3963 (3) | 0.76189 (9) | 0.0555 (5) | |
H4A | 0.6874 | 0.5123 | 0.7751 | 0.067* | |
H4B | 0.6746 | 0.3179 | 0.7745 | 0.067* | |
C5 | 0.4224 (3) | 0.3675 (2) | 0.79797 (9) | 0.0517 (4) | |
C6 | 0.0524 (3) | 0.0373 (3) | 0.66718 (11) | 0.0669 (6) | |
H6 | −0.0557 | 0.0324 | 0.6894 | 0.080* | |
C7 | 0.0072 (4) | −0.0812 (3) | 0.60512 (11) | 0.0709 (6) | |
C8 | −0.1871 (5) | −0.1395 (4) | 0.57069 (13) | 0.0918 (8) | |
C9 | −0.2464 (6) | −0.2508 (4) | 0.51297 (16) | 0.1186 (12) | |
H9 | −0.3799 | −0.2870 | 0.4924 | 0.142* | |
C10 | −0.1096 (8) | −0.3085 (4) | 0.48576 (17) | 0.1295 (15) | |
H10 | −0.1470 | −0.3816 | 0.4455 | 0.155* | |
C11 | 0.0855 (7) | −0.2578 (4) | 0.51830 (17) | 0.1190 (12) | |
H11 | 0.1796 | −0.2993 | 0.5004 | 0.143* | |
C12 | 0.1434 (5) | −0.1460 (3) | 0.57746 (14) | 0.0932 (8) | |
H12 | 0.2759 | −0.1140 | 0.5989 | 0.112* | |
C13 | 0.4239 (3) | 0.4449 (2) | 0.85882 (9) | 0.0529 (4) | |
H13 | 0.2995 | 0.4232 | 0.8724 | 0.064* | |
C14 | 0.5907 (3) | 0.5585 (2) | 0.90749 (9) | 0.0502 (4) | |
C15 | 0.5489 (2) | 0.6679 (2) | 0.95580 (9) | 0.0508 (4) | |
H15 | 0.4176 | 0.6703 | 0.9541 | 0.061* | |
C16 | 0.6949 (3) | 0.7734 (2) | 1.00643 (9) | 0.0502 (4) | |
C17 | 0.8914 (3) | 0.7676 (3) | 1.00944 (10) | 0.0589 (5) | |
H17 | 0.9920 | 0.8359 | 1.0432 | 0.071* | |
C18 | 0.9348 (3) | 0.6604 (3) | 0.96222 (10) | 0.0622 (5) | |
H18 | 1.0663 | 0.6583 | 0.9643 | 0.075* | |
C19 | 0.7894 (3) | 0.5553 (3) | 0.91160 (10) | 0.0563 (5) | |
H19 | 0.8231 | 0.4830 | 0.8805 | 0.068* | |
C20 | 0.7547 (3) | 0.9895 (2) | 1.09784 (10) | 0.0544 (5) | |
H20 | 0.8902 | 1.0190 | 1.0949 | 0.065* | |
C21 | 0.6905 (3) | 1.0785 (2) | 1.15058 (9) | 0.0513 (4) | |
C22 | 0.4890 (2) | 1.0333 (2) | 1.15879 (9) | 0.0506 (4) | |
C23 | 0.4332 (3) | 1.1183 (2) | 1.21175 (10) | 0.0563 (5) | |
C24 | 0.5736 (3) | 1.2464 (3) | 1.25530 (11) | 0.0627 (5) | |
H24 | 0.5349 | 1.3020 | 1.2907 | 0.075* | |
C25 | 0.7720 (3) | 1.2933 (3) | 1.24698 (12) | 0.0688 (6) | |
H25 | 0.8661 | 1.3813 | 1.2762 | 0.083* | |
C26 | 0.8297 (3) | 1.2095 (3) | 1.19545 (11) | 0.0634 (5) | |
H26 | 0.9636 | 1.2406 | 1.1903 | 0.076* | |
C27 | 0.7062 (3) | 0.4162 (4) | 0.65468 (11) | 0.0833 (7) | |
H27A | 0.7912 | 0.3464 | 0.6662 | 0.125* | |
H27B | 0.7794 | 0.5346 | 0.6685 | 0.125* | |
H27C | 0.6621 | 0.3988 | 0.6067 | 0.125* | |
F1 | −0.3275 (3) | −0.0814 (3) | 0.59540 (10) | 0.1439 (8) | |
N1 | 0.5334 (2) | 0.3691 (2) | 0.68888 (8) | 0.0581 (4) | |
N2 | 0.6306 (2) | 0.8707 (2) | 1.05465 (8) | 0.0535 (4) | |
O1 | 0.0748 (2) | 0.2306 (2) | 0.78767 (8) | 0.0775 (5) | |
O2 | 0.34485 (18) | 0.90889 (19) | 1.11746 (7) | 0.0647 (4) | |
H2 | 0.3942 | 0.8690 | 1.0880 | 0.097* | |
O3 | 0.2381 (2) | 1.0789 (2) | 1.22059 (10) | 0.0835 (5) | |
H3 | 0.1763 | 0.9836 | 1.2007 | 0.125* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0451 (9) | 0.0594 (11) | 0.0584 (11) | 0.0086 (8) | 0.0061 (8) | 0.0079 (9) |
C2 | 0.0543 (11) | 0.0554 (11) | 0.0575 (11) | 0.0111 (9) | 0.0032 (9) | 0.0075 (9) |
C3 | 0.0575 (11) | 0.0668 (13) | 0.0587 (12) | 0.0162 (10) | 0.0067 (9) | 0.0025 (10) |
C4 | 0.0454 (9) | 0.0649 (12) | 0.0507 (10) | 0.0101 (9) | 0.0036 (8) | 0.0071 (9) |
C5 | 0.0425 (9) | 0.0571 (11) | 0.0518 (10) | 0.0106 (8) | 0.0030 (7) | 0.0086 (8) |
C6 | 0.0602 (12) | 0.0691 (13) | 0.0594 (12) | 0.0039 (10) | 0.0047 (9) | 0.0044 (10) |
C7 | 0.0807 (14) | 0.0568 (13) | 0.0590 (12) | 0.0005 (11) | 0.0004 (11) | 0.0057 (10) |
C8 | 0.0927 (19) | 0.0898 (19) | 0.0680 (15) | −0.0004 (15) | −0.0060 (14) | −0.0016 (14) |
C9 | 0.144 (3) | 0.101 (2) | 0.0722 (19) | 0.001 (2) | −0.0284 (19) | −0.0048 (17) |
C10 | 0.213 (5) | 0.074 (2) | 0.0698 (19) | 0.014 (3) | −0.013 (2) | −0.0084 (15) |
C11 | 0.181 (4) | 0.0757 (19) | 0.096 (2) | 0.039 (2) | 0.018 (2) | −0.0132 (17) |
C12 | 0.116 (2) | 0.0678 (15) | 0.0877 (18) | 0.0232 (15) | 0.0082 (16) | −0.0056 (14) |
C13 | 0.0430 (9) | 0.0597 (11) | 0.0531 (11) | 0.0105 (8) | 0.0058 (8) | 0.0109 (9) |
C14 | 0.0426 (9) | 0.0589 (11) | 0.0469 (9) | 0.0109 (8) | 0.0058 (7) | 0.0131 (8) |
C15 | 0.0370 (8) | 0.0642 (11) | 0.0499 (10) | 0.0126 (8) | 0.0051 (7) | 0.0122 (9) |
C16 | 0.0428 (9) | 0.0596 (11) | 0.0464 (9) | 0.0117 (8) | 0.0057 (7) | 0.0114 (8) |
C17 | 0.0413 (9) | 0.0712 (13) | 0.0576 (11) | 0.0116 (9) | −0.0011 (8) | 0.0051 (10) |
C18 | 0.0400 (9) | 0.0826 (14) | 0.0629 (12) | 0.0193 (9) | 0.0034 (8) | 0.0073 (11) |
C19 | 0.0461 (9) | 0.0687 (12) | 0.0549 (11) | 0.0188 (9) | 0.0067 (8) | 0.0090 (9) |
C20 | 0.0392 (9) | 0.0594 (11) | 0.0616 (11) | 0.0089 (8) | 0.0091 (8) | 0.0099 (9) |
C21 | 0.0413 (9) | 0.0526 (10) | 0.0571 (10) | 0.0108 (8) | 0.0041 (8) | 0.0090 (8) |
C22 | 0.0387 (8) | 0.0515 (10) | 0.0570 (10) | 0.0086 (8) | 0.0015 (7) | 0.0087 (9) |
C23 | 0.0443 (9) | 0.0557 (11) | 0.0699 (12) | 0.0146 (8) | 0.0111 (9) | 0.0113 (10) |
C24 | 0.0619 (12) | 0.0553 (12) | 0.0701 (13) | 0.0188 (10) | 0.0084 (10) | 0.0017 (10) |
C25 | 0.0552 (11) | 0.0574 (12) | 0.0833 (15) | 0.0112 (10) | −0.0032 (10) | −0.0070 (11) |
C26 | 0.0415 (9) | 0.0600 (12) | 0.0798 (14) | 0.0068 (9) | 0.0024 (9) | −0.0009 (11) |
C27 | 0.0636 (13) | 0.110 (2) | 0.0613 (13) | 0.0016 (13) | 0.0153 (10) | 0.0053 (13) |
F1 | 0.0777 (11) | 0.196 (2) | 0.1196 (15) | 0.0102 (12) | −0.0175 (10) | −0.0350 (14) |
N1 | 0.0495 (8) | 0.0659 (10) | 0.0512 (9) | 0.0063 (7) | 0.0056 (7) | 0.0069 (8) |
N2 | 0.0440 (8) | 0.0626 (10) | 0.0511 (8) | 0.0128 (7) | 0.0046 (6) | 0.0083 (7) |
O1 | 0.0467 (7) | 0.0905 (11) | 0.0807 (10) | 0.0032 (7) | 0.0116 (7) | −0.0136 (9) |
O2 | 0.0396 (6) | 0.0729 (9) | 0.0702 (9) | 0.0058 (6) | 0.0019 (6) | −0.0051 (7) |
O3 | 0.0527 (8) | 0.0830 (11) | 0.1097 (14) | 0.0099 (8) | 0.0289 (9) | −0.0068 (10) |
Geometric parameters (Å, º) top
C1—O1 | 1.228 (2) | C15—C16 | 1.386 (2) |
C1—C2 | 1.485 (3) | C15—H15 | 0.9300 |
C1—C5 | 1.490 (2) | C16—C17 | 1.397 (2) |
C2—C6 | 1.339 (3) | C16—N2 | 1.413 (2) |
C2—C3 | 1.504 (3) | C17—C18 | 1.370 (3) |
C3—N1 | 1.454 (2) | C17—H17 | 0.9300 |
C3—H3A | 0.9700 | C18—C19 | 1.383 (3) |
C3—H3B | 0.9700 | C18—H18 | 0.9300 |
C4—N1 | 1.461 (2) | C19—H19 | 0.9300 |
C4—C5 | 1.504 (2) | C20—N2 | 1.285 (2) |
C4—H4A | 0.9700 | C20—C21 | 1.438 (3) |
C4—H4B | 0.9700 | C20—H20 | 0.9300 |
C5—C13 | 1.334 (3) | C21—C26 | 1.395 (3) |
C6—C7 | 1.462 (3) | C21—C22 | 1.402 (2) |
C6—H6 | 0.9300 | C22—O2 | 1.349 (2) |
C7—C8 | 1.382 (3) | C22—C23 | 1.392 (3) |
C7—C12 | 1.383 (4) | C23—O3 | 1.363 (2) |
C8—F1 | 1.352 (4) | C23—C24 | 1.373 (3) |
C8—C9 | 1.359 (4) | C24—C25 | 1.382 (3) |
C9—C10 | 1.351 (5) | C24—H24 | 0.9300 |
C9—H9 | 0.9300 | C25—C26 | 1.371 (3) |
C10—C11 | 1.374 (5) | C25—H25 | 0.9300 |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C11—C12 | 1.384 (4) | C27—N1 | 1.455 (3) |
C11—H11 | 0.9300 | C27—H27A | 0.9600 |
C12—H12 | 0.9300 | C27—H27B | 0.9600 |
C13—C14 | 1.462 (2) | C27—H27C | 0.9600 |
C13—H13 | 0.9300 | O2—H2 | 0.8200 |
C14—C15 | 1.391 (3) | O3—H3 | 0.8200 |
C14—C19 | 1.404 (2) | | |
| | | |
O1—C1—C2 | 121.63 (18) | C16—C15—C14 | 122.73 (16) |
O1—C1—C5 | 120.61 (18) | C16—C15—H15 | 118.6 |
C2—C1—C5 | 117.72 (17) | C14—C15—H15 | 118.6 |
C6—C2—C1 | 117.68 (19) | C15—C16—C17 | 118.46 (18) |
C6—C2—C3 | 124.9 (2) | C15—C16—N2 | 117.02 (15) |
C1—C2—C3 | 117.39 (17) | C17—C16—N2 | 124.35 (17) |
N1—C3—C2 | 110.07 (17) | C18—C17—C16 | 119.45 (18) |
N1—C3—H3A | 109.6 | C18—C17—H17 | 120.3 |
C2—C3—H3A | 109.6 | C16—C17—H17 | 120.3 |
N1—C3—H3B | 109.6 | C17—C18—C19 | 122.18 (17) |
C2—C3—H3B | 109.6 | C17—C18—H18 | 118.9 |
H3A—C3—H3B | 108.2 | C19—C18—H18 | 118.9 |
N1—C4—C5 | 110.19 (15) | C18—C19—C14 | 119.50 (19) |
N1—C4—H4A | 109.6 | C18—C19—H19 | 120.2 |
C5—C4—H4A | 109.6 | C14—C19—H19 | 120.2 |
N1—C4—H4B | 109.6 | N2—C20—C21 | 122.05 (16) |
C5—C4—H4B | 109.6 | N2—C20—H20 | 119.0 |
H4A—C4—H4B | 108.1 | C21—C20—H20 | 119.0 |
C13—C5—C1 | 116.90 (17) | C26—C21—C22 | 118.86 (18) |
C13—C5—C4 | 124.98 (17) | C26—C21—C20 | 120.18 (17) |
C1—C5—C4 | 118.07 (17) | C22—C21—C20 | 120.95 (17) |
C2—C6—C7 | 130.0 (2) | O2—C22—C23 | 117.92 (16) |
C2—C6—H6 | 115.0 | O2—C22—C21 | 122.65 (18) |
C7—C6—H6 | 115.0 | C23—C22—C21 | 119.43 (17) |
C8—C7—C12 | 115.4 (2) | O3—C23—C24 | 118.72 (19) |
C8—C7—C6 | 119.1 (3) | O3—C23—C22 | 120.85 (18) |
C12—C7—C6 | 125.4 (2) | C24—C23—C22 | 120.41 (17) |
F1—C8—C9 | 117.6 (3) | C23—C24—C25 | 120.5 (2) |
F1—C8—C7 | 118.2 (2) | C23—C24—H24 | 119.8 |
C9—C8—C7 | 124.2 (3) | C25—C24—H24 | 119.8 |
C10—C9—C8 | 119.4 (4) | C26—C25—C24 | 119.8 (2) |
C10—C9—H9 | 120.3 | C26—C25—H25 | 120.1 |
C8—C9—H9 | 120.3 | C24—C25—H25 | 120.1 |
C9—C10—C11 | 119.2 (3) | C25—C26—C21 | 121.01 (18) |
C9—C10—H10 | 120.4 | C25—C26—H26 | 119.5 |
C11—C10—H10 | 120.4 | C21—C26—H26 | 119.5 |
C10—C11—C12 | 120.8 (4) | N1—C27—H27A | 109.5 |
C10—C11—H11 | 119.6 | N1—C27—H27B | 109.5 |
C12—C11—H11 | 119.6 | H27A—C27—H27B | 109.5 |
C7—C12—C11 | 121.0 (3) | N1—C27—H27C | 109.5 |
C7—C12—H12 | 119.5 | H27A—C27—H27C | 109.5 |
C11—C12—H12 | 119.5 | H27B—C27—H27C | 109.5 |
C5—C13—C14 | 130.11 (18) | C3—N1—C27 | 111.12 (18) |
C5—C13—H13 | 114.9 | C3—N1—C4 | 109.22 (16) |
C14—C13—H13 | 114.9 | C27—N1—C4 | 109.67 (15) |
C15—C14—C19 | 117.67 (17) | C20—N2—C16 | 122.06 (15) |
C15—C14—C13 | 118.32 (16) | C22—O2—H2 | 109.5 |
C19—C14—C13 | 123.84 (18) | C23—O3—H3 | 109.5 |
| | | |
O1—C1—C2—C6 | −2.0 (3) | C13—C14—C15—C16 | 176.28 (16) |
C5—C1—C2—C6 | 175.59 (17) | C14—C15—C16—C17 | −0.9 (3) |
O1—C1—C2—C3 | 177.15 (19) | C14—C15—C16—N2 | −176.31 (16) |
C5—C1—C2—C3 | −5.3 (3) | C15—C16—C17—C18 | 0.8 (3) |
C6—C2—C3—N1 | 148.4 (2) | N2—C16—C17—C18 | 175.89 (18) |
C1—C2—C3—N1 | −30.7 (2) | C16—C17—C18—C19 | −0.8 (3) |
O1—C1—C5—C13 | 2.3 (3) | C17—C18—C19—C14 | 0.7 (3) |
C2—C1—C5—C13 | −175.28 (17) | C15—C14—C19—C18 | −0.7 (3) |
O1—C1—C5—C4 | −175.10 (19) | C13—C14—C19—C18 | −175.86 (18) |
C2—C1—C5—C4 | 7.3 (3) | N2—C20—C21—C26 | −178.46 (18) |
N1—C4—C5—C13 | −150.57 (19) | N2—C20—C21—C22 | 2.8 (3) |
N1—C4—C5—C1 | 26.6 (2) | C26—C21—C22—O2 | 179.61 (18) |
C1—C2—C6—C7 | −177.2 (2) | C20—C21—C22—O2 | −1.6 (3) |
C3—C2—C6—C7 | 3.8 (4) | C26—C21—C22—C23 | −0.8 (3) |
C2—C6—C7—C8 | −155.8 (2) | C20—C21—C22—C23 | 177.90 (17) |
C2—C6—C7—C12 | 26.0 (4) | O2—C22—C23—O3 | −1.2 (3) |
C12—C7—C8—F1 | 179.7 (3) | C21—C22—C23—O3 | 179.18 (18) |
C6—C7—C8—F1 | 1.2 (4) | O2—C22—C23—C24 | −179.85 (17) |
C12—C7—C8—C9 | −0.9 (4) | C21—C22—C23—C24 | 0.6 (3) |
C6—C7—C8—C9 | −179.4 (3) | O3—C23—C24—C25 | −178.3 (2) |
F1—C8—C9—C10 | 178.4 (3) | C22—C23—C24—C25 | 0.3 (3) |
C7—C8—C9—C10 | −1.0 (5) | C23—C24—C25—C26 | −1.0 (3) |
C8—C9—C10—C11 | 2.2 (6) | C24—C25—C26—C21 | 0.7 (3) |
C9—C10—C11—C12 | −1.5 (5) | C22—C21—C26—C25 | 0.2 (3) |
C8—C7—C12—C11 | 1.7 (4) | C20—C21—C26—C25 | −178.56 (19) |
C6—C7—C12—C11 | 180.0 (2) | C2—C3—N1—C27 | −172.11 (17) |
C10—C11—C12—C7 | −0.5 (5) | C2—C3—N1—C4 | 66.8 (2) |
C1—C5—C13—C14 | 176.21 (18) | C5—C4—N1—C3 | −64.5 (2) |
C4—C5—C13—C14 | −6.6 (3) | C5—C4—N1—C27 | 173.51 (18) |
C5—C13—C14—C15 | 158.11 (19) | C21—C20—N2—C16 | −174.52 (16) |
C5—C13—C14—C19 | −26.7 (3) | C15—C16—N2—C20 | −170.10 (17) |
C19—C14—C15—C16 | 0.8 (3) | C17—C16—N2—C20 | 14.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 2.33 | 2.723 (2) | 110 |
O2—H2···N2 | 0.82 | 1.88 | 2.603 (2) | 146 |
C17—H17···O2i | 0.93 | 2.61 | 3.456 (2) | 152 |
C12—H12···F1i | 0.93 | 2.75 | 3.588 (4) | 150 |
O3—H3···O1ii | 0.82 | 2.17 | 2.829 (2) | 138 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+2. |
Cytotoxicity activities of (5), (6) and (12) presented as
IC50 (µM) topCompound | IC50 (µM) | | |
HepG2 | THP-1 | LO2 | |
(5) | 4.24±0.61 | 3.15±0.23 | 16.18±1.39 |
(6) | 10.32±0.18 | 8.66±0.82 | 27.21±0.95 |
(12) | 2.86±0.05 | 2.54±0.32 | 12.3±0.26 |
Curcumin | 13.78±0.31 | 22.54±0.34 | 25.67±0.23 |