Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618006605/ov3110sup1.cif
Contains datablocks exp_2471, exp_2473, exp_2476, global

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618006605/ov3110exp_2471sup2.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618006605/ov3110exp_2473sup3.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618006605/ov3110exp_2476sup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006605/ov3110exp_2471sup5.hkl
Contains datablock exp_2471

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006605/ov3110exp_2473sup6.hkl
Contains datablock exp_2473

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006605/ov3110exp_2476sup7.hkl
Contains datablock exp_2476

CCDC references: 1823142; 1823143; 1823144

Computing details top

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).

(5E)-3-(4-tert-Butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one (exp_2471) top
Crystal data top
C24H26FNOF(000) = 776
Mr = 363.46Dx = 1.168 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 13.4219 (4) ÅCell parameters from 2876 reflections
b = 8.3679 (3) Åθ = 5.4–70.0°
c = 18.5974 (7) ŵ = 0.61 mm1
β = 98.348 (3)°T = 293 K
V = 2066.60 (12) Å3Block, clear pale yellow
Z = 40.52 × 0.40 × 0.24 mm
Data collection top
SuperNova (Cu) X-ray Source
diffractometer
3891 independent reflections
Radiation source: micro-focus sealed X-ray tube2903 reflections with I > 2σ(I)
Detector resolution: 8.22 pixels mm-1Rint = 0.019
ω scansθmax = 70.8°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 1615
Tmin = 0.572, Tmax = 1.000k = 107
7470 measured reflectionsl = 2217
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.01006 (13)0.0592 (2)0.17854 (9)0.0678 (4)
C20.11752 (14)0.0518 (2)0.16597 (10)0.0765 (5)
C30.19730 (13)0.0621 (2)0.23019 (9)0.0670 (4)
C40.16431 (13)0.0808 (2)0.30345 (9)0.0705 (5)
H4A0.21540.03710.34050.085*
H4B0.15660.19340.31370.085*
C50.01030 (13)0.0737 (2)0.25540 (10)0.0708 (5)
H5A0.01510.18570.26780.085*
H5B0.07420.02340.25990.085*
C60.06101 (14)0.0486 (2)0.12008 (10)0.0725 (5)
H60.03690.03470.07610.087*
C70.17038 (13)0.0558 (2)0.11504 (9)0.0672 (4)
C80.22864 (15)0.0255 (2)0.05828 (10)0.0773 (5)
H80.19690.08270.02520.093*
C90.33196 (15)0.0227 (3)0.05037 (11)0.0842 (6)
H90.37020.07850.01280.101*
C100.37731 (14)0.0637 (2)0.09868 (11)0.0793 (5)
C110.32444 (14)0.1479 (2)0.15435 (10)0.0809 (5)
H110.35740.20700.18610.097*
C120.22069 (14)0.1430 (2)0.16238 (10)0.0742 (5)
H120.18350.19930.20030.089*
C130.29299 (13)0.0472 (2)0.21867 (10)0.0694 (4)
H130.30130.03280.17030.083*
C140.38634 (12)0.04997 (19)0.26963 (9)0.0624 (4)
C150.46775 (13)0.0381 (2)0.25342 (10)0.0736 (5)
H150.46130.09560.21020.088*
C160.55769 (13)0.0427 (2)0.29938 (10)0.0737 (5)
H160.60960.10570.28690.088*
C170.57350 (12)0.04382 (19)0.36380 (9)0.0625 (4)
C180.49242 (13)0.1352 (2)0.37896 (10)0.0697 (4)
H180.49990.19640.42110.084*
C190.40119 (13)0.1383 (2)0.33365 (10)0.0704 (4)
H190.34890.20050.34620.084*
C200.04314 (15)0.0010 (3)0.37904 (11)0.0908 (6)
H20A0.03750.10720.39500.136*
H20B0.09470.05500.41120.136*
H20C0.02000.05500.37920.136*
C210.67402 (14)0.0415 (2)0.41374 (10)0.0720 (5)
C220.7442 (4)0.1001 (7)0.3991 (3)0.113 (2)0.562 (6)
H22A0.70990.19950.40350.169*0.562 (6)
H22B0.80450.09710.43380.169*0.562 (6)
H22C0.76130.09080.35090.169*0.562 (6)
C230.6581 (4)0.0238 (9)0.4940 (2)0.122 (3)0.562 (6)
H23A0.61790.11110.50710.183*0.562 (6)
H23B0.72220.02450.52460.183*0.562 (6)
H23C0.62420.07520.50020.183*0.562 (6)
C240.7321 (4)0.1956 (7)0.4047 (3)0.115 (2)0.562 (6)
H24A0.74490.20420.35540.173*0.562 (6)
H24B0.79490.19370.43680.173*0.562 (6)
H24C0.69290.28560.41620.173*0.562 (6)
C22'0.6850 (6)0.1217 (7)0.4461 (4)0.113 (3)0.438 (6)
H22D0.74930.13060.47610.169*0.438 (6)
H22E0.68040.19980.40800.169*0.438 (6)
H22F0.63240.13980.47510.169*0.438 (6)
C23'0.6760 (5)0.1680 (9)0.4721 (4)0.124 (3)0.438 (6)
H23D0.62520.14480.50200.186*0.438 (6)
H23E0.66300.27080.44980.186*0.438 (6)
H23F0.74090.16880.50160.186*0.438 (6)
C24'0.7554 (4)0.0798 (13)0.3666 (4)0.124 (3)0.438 (6)
H24D0.81900.09350.39710.186*0.438 (6)
H24E0.73810.17640.33980.186*0.438 (6)
H24F0.76030.00660.33330.186*0.438 (6)
F10.47961 (9)0.06919 (19)0.08984 (8)0.1122 (5)
N10.06919 (10)0.00149 (18)0.30561 (7)0.0680 (4)
O10.13921 (11)0.0391 (3)0.10479 (8)0.1166 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0702 (10)0.0645 (10)0.0675 (10)0.0039 (8)0.0059 (8)0.0006 (8)
C20.0738 (11)0.0920 (14)0.0641 (10)0.0028 (9)0.0114 (8)0.0027 (9)
C30.0661 (10)0.0688 (10)0.0668 (10)0.0023 (7)0.0126 (8)0.0011 (8)
C40.0648 (10)0.0790 (11)0.0679 (10)0.0002 (8)0.0096 (8)0.0078 (8)
C50.0649 (10)0.0748 (11)0.0714 (10)0.0056 (8)0.0057 (8)0.0018 (8)
C60.0751 (11)0.0744 (11)0.0676 (10)0.0024 (8)0.0085 (8)0.0014 (8)
C70.0735 (10)0.0643 (10)0.0612 (9)0.0002 (8)0.0017 (8)0.0032 (7)
C80.0866 (12)0.0836 (12)0.0600 (10)0.0037 (9)0.0046 (9)0.0047 (9)
C90.0826 (13)0.0947 (14)0.0709 (11)0.0155 (10)0.0041 (10)0.0031 (10)
C100.0655 (10)0.0927 (14)0.0766 (12)0.0047 (9)0.0003 (9)0.0104 (10)
C110.0775 (12)0.0861 (13)0.0764 (11)0.0087 (9)0.0025 (9)0.0064 (9)
C120.0747 (11)0.0720 (11)0.0714 (10)0.0050 (8)0.0050 (8)0.0087 (8)
C130.0717 (10)0.0734 (11)0.0649 (10)0.0043 (8)0.0161 (8)0.0018 (8)
C140.0620 (9)0.0630 (10)0.0652 (9)0.0078 (7)0.0197 (7)0.0003 (7)
C150.0696 (10)0.0863 (13)0.0684 (10)0.0067 (9)0.0225 (8)0.0176 (9)
C160.0654 (10)0.0801 (12)0.0787 (11)0.0002 (8)0.0214 (9)0.0155 (9)
C170.0660 (9)0.0590 (9)0.0653 (9)0.0078 (7)0.0190 (7)0.0005 (7)
C180.0724 (10)0.0691 (10)0.0701 (10)0.0058 (8)0.0185 (8)0.0132 (8)
C190.0673 (10)0.0678 (10)0.0793 (11)0.0006 (8)0.0210 (8)0.0128 (8)
C200.0753 (12)0.1267 (17)0.0720 (12)0.0055 (11)0.0165 (10)0.0069 (12)
C210.0706 (10)0.0719 (11)0.0739 (11)0.0027 (8)0.0117 (8)0.0016 (8)
C220.084 (3)0.121 (4)0.127 (4)0.025 (3)0.005 (3)0.015 (3)
C230.104 (3)0.190 (8)0.070 (2)0.026 (4)0.004 (2)0.020 (3)
C240.095 (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)
F10.0698 (7)0.1568 (13)0.1058 (9)0.0070 (7)0.0014 (6)0.0017 (8)
N10.0606 (8)0.0799 (9)0.0633 (8)0.0042 (7)0.0088 (6)0.0036 (7)
O10.0832 (10)0.201 (2)0.0664 (9)0.0037 (10)0.0137 (7)0.0094 (10)
Geometric parameters (Å, º) top
C1—C61.341 (2)C17—C181.392 (2)
C1—C21.496 (3)C17—C211.523 (2)
C1—C51.499 (2)C18—C191.382 (2)
C2—O11.219 (2)C18—H180.9300
C2—C31.486 (3)C19—H190.9300
C3—C131.338 (2)C20—N11.458 (2)
C3—C41.501 (2)C20—H20A0.9600
C4—N11.456 (2)C20—H20B0.9600
C4—H4A0.9700C20—H20C0.9600
C4—H4B0.9700C21—C22'1.492 (6)
C5—N11.455 (2)C21—C23'1.514 (6)
C5—H5A0.9700C21—C241.528 (5)
C5—H5B0.9700C21—C24'1.531 (6)
C6—C71.459 (3)C21—C231.546 (5)
C6—H60.9300C21—C221.562 (5)
C7—C121.392 (2)C22—H22A0.9600
C7—C81.396 (2)C22—H22B0.9600
C8—C91.373 (3)C22—H22C0.9600
C8—H80.9300C23—H23A0.9600
C9—C101.363 (3)C23—H23B0.9600
C9—H90.9300C23—H23C0.9600
C10—F11.360 (2)C24—H24A0.9600
C10—C111.363 (3)C24—H24B0.9600
C11—C121.379 (3)C24—H24C0.9600
C11—H110.9300C22'—H22D0.9600
C12—H120.9300C22'—H22E0.9600
C13—C141.457 (2)C22'—H22F0.9600
C13—H130.9300C23'—H23D0.9600
C14—C151.387 (2)C23'—H23E0.9600
C14—C191.391 (2)C23'—H23F0.9600
C15—C161.375 (3)C24'—H24D0.9600
C15—H150.9300C24'—H24E0.9600
C16—C171.389 (2)C24'—H24F0.9600
C16—H160.9300
C6—C1—C2117.33 (17)C18—C19—C14121.06 (16)
C6—C1—C5124.88 (17)C18—C19—H19119.5
C2—C1—C5117.78 (15)C14—C19—H19119.5
O1—C2—C3120.87 (18)N1—C20—H20A109.5
O1—C2—C1121.06 (17)N1—C20—H20B109.5
C3—C2—C1118.07 (16)H20A—C20—H20B109.5
C13—C3—C2117.53 (17)N1—C20—H20C109.5
C13—C3—C4124.86 (16)H20A—C20—H20C109.5
C2—C3—C4117.55 (15)H20B—C20—H20C109.5
N1—C4—C3110.57 (14)C22'—C21—C23'111.2 (4)
N1—C4—H4A109.5C22'—C21—C17106.5 (3)
C3—C4—H4A109.5C23'—C21—C17110.5 (3)
N1—C4—H4B109.5C17—C21—C24110.0 (2)
C3—C4—H4B109.5C22'—C21—C24'112.7 (5)
H4A—C4—H4B108.1C23'—C21—C24'109.0 (5)
N1—C5—C1111.03 (14)C17—C21—C24'106.9 (3)
N1—C5—H5A109.4C17—C21—C23110.8 (2)
C1—C5—H5A109.4C24—C21—C23109.4 (4)
N1—C5—H5B109.4C17—C21—C22114.0 (2)
C1—C5—H5B109.4C24—C21—C22106.9 (4)
H5A—C5—H5B108.0C23—C21—C22105.5 (3)
C1—C6—C7129.80 (18)C21—C22—H22A109.5
C1—C6—H6115.1C21—C22—H22B109.5
C7—C6—H6115.1H22A—C22—H22B109.5
C12—C7—C8117.65 (17)C21—C22—H22C109.5
C12—C7—C6123.86 (16)H22A—C22—H22C109.5
C8—C7—C6118.46 (17)H22B—C22—H22C109.5
C9—C8—C7121.24 (19)C21—C23—H23A109.5
C9—C8—H8119.4C21—C23—H23B109.5
C7—C8—H8119.4H23A—C23—H23B109.5
C10—C9—C8118.62 (18)C21—C23—H23C109.5
C10—C9—H9120.7H23A—C23—H23C109.5
C8—C9—H9120.7H23B—C23—H23C109.5
F1—C10—C11118.65 (19)C21—C24—H24A109.5
F1—C10—C9118.54 (18)C21—C24—H24B109.5
C11—C10—C9122.79 (18)H24A—C24—H24B109.5
C10—C11—C12118.23 (19)C21—C24—H24C109.5
C10—C11—H11120.9H24A—C24—H24C109.5
C12—C11—H11120.9H24B—C24—H24C109.5
C11—C12—C7121.46 (17)C21—C22'—H22D109.5
C11—C12—H12119.3C21—C22'—H22E109.5
C7—C12—H12119.3H22D—C22'—H22E109.5
C3—C13—C14130.47 (17)C21—C22'—H22F109.5
C3—C13—H13114.8H22D—C22'—H22F109.5
C14—C13—H13114.8H22E—C22'—H22F109.5
C15—C14—C19116.68 (16)C21—C23'—H23D109.5
C15—C14—C13118.71 (16)C21—C23'—H23E109.5
C19—C14—C13124.60 (16)H23D—C23'—H23E109.5
C16—C15—C14121.89 (16)C21—C23'—H23F109.5
C16—C15—H15119.1H23D—C23'—H23F109.5
C14—C15—H15119.1H23E—C23'—H23F109.5
C15—C16—C17122.13 (17)C21—C24'—H24D109.5
C15—C16—H16118.9C21—C24'—H24E109.5
C17—C16—H16118.9H24D—C24'—H24E109.5
C16—C17—C18115.78 (16)C21—C24'—H24F109.5
C16—C17—C21122.02 (16)H24D—C24'—H24F109.5
C18—C17—C21122.19 (15)H24E—C24'—H24F109.5
C19—C18—C17122.44 (16)C5—N1—C4110.01 (15)
C19—C18—H18118.8C5—N1—C20110.29 (14)
C17—C18—H18118.8C4—N1—C20110.80 (14)
C6—C1—C2—O11.1 (3)C3—C13—C14—C15149.89 (19)
C5—C1—C2—O1179.6 (2)C3—C13—C14—C1931.6 (3)
C6—C1—C2—C3179.58 (16)C19—C14—C15—C162.2 (3)
C5—C1—C2—C31.0 (2)C13—C14—C15—C16179.16 (17)
O1—C2—C3—C134.0 (3)C14—C15—C16—C171.8 (3)
C1—C2—C3—C13176.69 (16)C15—C16—C17—C180.1 (3)
O1—C2—C3—C4178.8 (2)C15—C16—C17—C21178.55 (17)
C1—C2—C3—C40.5 (2)C16—C17—C18—C191.0 (3)
C13—C3—C4—N1144.49 (17)C21—C17—C18—C19179.67 (16)
C2—C3—C4—N132.5 (2)C17—C18—C19—C140.5 (3)
C6—C1—C5—N1148.92 (18)C15—C14—C19—C181.1 (3)
C2—C1—C5—N129.5 (2)C13—C14—C19—C18179.62 (16)
C2—C1—C6—C7178.40 (17)C16—C17—C21—C22'69.4 (4)
C5—C1—C6—C73.2 (3)C18—C17—C21—C22'112.0 (4)
C1—C6—C7—C1230.3 (3)C16—C17—C21—C23'169.8 (4)
C1—C6—C7—C8151.62 (19)C18—C17—C21—C23'8.8 (5)
C12—C7—C8—C91.5 (3)C16—C17—C21—C24103.0 (4)
C6—C7—C8—C9179.66 (18)C18—C17—C21—C2475.6 (4)
C7—C8—C9—C101.0 (3)C16—C17—C21—C24'51.3 (5)
C8—C9—C10—F1178.59 (18)C18—C17—C21—C24'127.3 (5)
C8—C9—C10—C110.3 (3)C16—C17—C21—C23135.9 (3)
F1—C10—C11—C12179.27 (17)C18—C17—C21—C2345.5 (4)
C9—C10—C11—C121.0 (3)C16—C17—C21—C2217.1 (4)
C10—C11—C12—C70.4 (3)C18—C17—C21—C22164.3 (3)
C8—C7—C12—C110.8 (3)C1—C5—N1—C463.39 (19)
C6—C7—C12—C11178.85 (17)C1—C5—N1—C20174.09 (16)
C2—C3—C13—C14179.20 (17)C3—C4—N1—C564.96 (19)
C4—C3—C13—C142.2 (3)C3—C4—N1—C20172.82 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.932.673.422 (2)139
C15—H15···F1ii0.932.843.344 (2)115
C9—H9···F1iii0.932.573.381 (2)146
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x1, y, z.
(5E)-3-(4-tert-Butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one (exp_2473) top
Crystal data top
C26H31NO3F(000) = 872
Mr = 405.52Dx = 1.157 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 19.1378 (9) ÅCell parameters from 3159 reflections
b = 16.2788 (8) Åθ = 4.7–70.3°
c = 7.5525 (4) ŵ = 0.59 mm1
β = 98.386 (5)°T = 293 K
V = 2327.8 (2) Å3Block, clear pale yellow
Z = 40.52 × 0.40 × 0.24 mm
Data collection top
SuperNova (Cu) X-ray Source
diffractometer
4384 independent reflections
Radiation source: micro-focus sealed X-ray tube3392 reflections with I > 2σ(I)
Detector resolution: 8.22 pixels mm-1Rint = 0.017
ω scansθmax = 71.1°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 2320
Tmin = 0.656, Tmax = 1.000k = 1819
8937 measured reflectionsl = 69
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-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 parametersΔρmax = 0.17 e Å3
6 restraintsΔρmin = 0.17 e Å3
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
xyzUiso*/UeqOcc. (<1)
C11.10312 (8)0.74376 (10)0.5015 (2)0.0518 (4)
C21.05524 (8)0.67263 (10)0.4555 (2)0.0532 (4)
C30.97825 (8)0.68992 (9)0.40452 (19)0.0479 (3)
C40.95536 (8)0.77779 (9)0.3912 (2)0.0505 (4)
H4A0.91260.78260.30550.061*
H4B0.94480.79620.50660.061*
C51.07319 (8)0.82826 (10)0.4694 (2)0.0551 (4)
H5A1.06170.85010.58110.066*
H5B1.10870.86360.43020.066*
C61.17117 (8)0.72718 (11)0.5650 (2)0.0591 (4)
H61.18240.67170.57760.071*
C71.23003 (8)0.78401 (11)0.6171 (2)0.0586 (4)
C81.29785 (8)0.75479 (12)0.6092 (2)0.0639 (4)
H81.30440.70070.57550.077*
C91.35546 (9)0.80611 (12)0.6515 (3)0.0681 (5)
C101.34641 (9)0.88608 (12)0.7031 (3)0.0715 (5)
H101.38530.92050.73010.086*
C111.27954 (9)0.91491 (12)0.7144 (2)0.0666 (5)
C121.22146 (9)0.86452 (12)0.6731 (2)0.0631 (4)
H121.17660.88430.68280.076*
C130.93464 (8)0.62534 (10)0.3737 (2)0.0515 (4)
H130.95690.57440.37950.062*
C140.85744 (8)0.62236 (9)0.3324 (2)0.0521 (4)
C150.82628 (9)0.55118 (11)0.2573 (3)0.0688 (5)
H150.85490.50810.23090.083*
C160.75383 (10)0.54255 (12)0.2206 (3)0.0787 (6)
H160.73510.49420.16800.094*
C170.70863 (9)0.60341 (11)0.2595 (3)0.0658 (5)
C180.73948 (9)0.67383 (11)0.3373 (3)0.0714 (5)
H180.71050.71620.36610.086*
C190.81192 (9)0.68365 (10)0.3739 (3)0.0652 (5)
H190.83050.73200.42720.078*
C201.44015 (11)0.69923 (15)0.6464 (4)0.0986 (8)
H20A1.42440.67340.74770.148*
H20B1.49030.69210.65290.148*
H20C1.41670.67460.53820.148*
C211.20856 (12)1.02983 (15)0.7716 (4)0.0999 (8)
H21A1.18141.02510.65470.150*
H21B1.21371.08680.80390.150*
H21C1.18481.00150.85700.150*
C220.98409 (10)0.91333 (10)0.3108 (3)0.0656 (5)
H22A0.94210.91390.22390.098*
H22B1.01960.94710.26960.098*
H22C0.97340.93430.42260.098*
C230.6324 (9)0.5969 (8)0.2341 (17)0.077 (6)0.314 (17)
C240.6033 (10)0.5143 (14)0.163 (6)0.224 (16)0.314 (17)
H24A0.62320.50040.05720.336*0.314 (17)
H24B0.55280.51770.13390.336*0.314 (17)
H24C0.61550.47280.25230.336*0.314 (17)
C250.6002 (7)0.6620 (19)0.099 (4)0.154 (9)0.314 (17)
H25A0.61280.71580.14520.231*0.314 (17)
H25B0.54970.65650.08010.231*0.314 (17)
H25C0.61800.65440.01220.231*0.314 (17)
C260.5908 (9)0.6165 (15)0.386 (2)0.139 (7)0.314 (17)
H26A0.60260.57760.48090.208*0.314 (17)
H26B0.54110.61320.34230.208*0.314 (17)
H26C0.60220.67090.42930.208*0.314 (17)
C23A0.6267 (4)0.5914 (4)0.2172 (12)0.090 (3)0.686 (17)
C24A0.6088 (4)0.5030 (5)0.2497 (13)0.130 (3)0.686 (17)
H24D0.55850.49640.23380.195*0.686 (17)
H24E0.62830.48780.36960.195*0.686 (17)
H24F0.62840.46840.16630.195*0.686 (17)
C25A0.6040 (4)0.6108 (7)0.0215 (13)0.143 (3)0.686 (17)
H25D0.55470.59870.01040.215*0.686 (17)
H25E0.63100.57810.05000.215*0.686 (17)
H25F0.61210.66800.00060.215*0.686 (17)
C26A0.5939 (4)0.6470 (10)0.344 (2)0.228 (8)0.686 (17)
H26D0.60630.70300.32420.342*0.686 (17)
H26E0.61120.63190.46540.342*0.686 (17)
H26F0.54350.64120.32260.342*0.686 (17)
N11.00996 (7)0.82979 (8)0.33549 (17)0.0515 (3)
O11.07785 (6)0.60222 (7)0.45855 (19)0.0718 (4)
O21.42411 (7)0.78390 (10)0.6466 (3)0.0979 (5)
O31.27653 (7)0.99442 (9)0.7703 (2)0.0933 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0411 (8)0.0655 (9)0.0492 (8)0.0034 (7)0.0079 (6)0.0024 (7)
C20.0438 (8)0.0629 (9)0.0538 (9)0.0003 (7)0.0094 (6)0.0031 (7)
C30.0429 (8)0.0575 (9)0.0434 (8)0.0004 (6)0.0066 (6)0.0035 (6)
C40.0418 (8)0.0583 (9)0.0511 (8)0.0021 (7)0.0054 (6)0.0035 (7)
C50.0453 (8)0.0635 (10)0.0560 (9)0.0084 (7)0.0059 (7)0.0040 (7)
C60.0465 (9)0.0731 (11)0.0575 (9)0.0015 (8)0.0071 (7)0.0004 (8)
C70.0407 (8)0.0782 (11)0.0560 (9)0.0041 (8)0.0039 (6)0.0007 (8)
C80.0441 (9)0.0755 (11)0.0711 (11)0.0013 (8)0.0056 (7)0.0028 (9)
C90.0388 (9)0.0846 (13)0.0805 (12)0.0011 (8)0.0071 (8)0.0036 (10)
C100.0464 (9)0.0814 (13)0.0840 (13)0.0102 (9)0.0007 (8)0.0000 (10)
C110.0540 (10)0.0757 (12)0.0677 (11)0.0029 (8)0.0013 (8)0.0074 (9)
C120.0420 (9)0.0841 (12)0.0622 (10)0.0013 (8)0.0044 (7)0.0076 (9)
C130.0457 (8)0.0553 (9)0.0527 (8)0.0024 (7)0.0042 (6)0.0056 (7)
C140.0447 (8)0.0530 (9)0.0571 (9)0.0003 (6)0.0024 (6)0.0028 (7)
C150.0501 (9)0.0599 (10)0.0944 (13)0.0019 (8)0.0034 (9)0.0199 (9)
C160.0512 (10)0.0698 (11)0.1102 (16)0.0048 (9)0.0045 (10)0.0303 (11)
C170.0440 (10)0.0650 (10)0.0848 (12)0.0016 (8)0.0022 (8)0.0012 (9)
C180.0481 (10)0.0564 (10)0.1098 (15)0.0052 (8)0.0111 (9)0.0021 (10)
C190.0500 (10)0.0540 (9)0.0919 (13)0.0034 (7)0.0113 (9)0.0105 (8)
C200.0537 (12)0.1033 (17)0.136 (2)0.0129 (11)0.0036 (12)0.0175 (15)
C210.0817 (15)0.1014 (17)0.1140 (18)0.0132 (13)0.0055 (13)0.0379 (14)
C220.0647 (11)0.0579 (10)0.0733 (11)0.0013 (8)0.0073 (8)0.0004 (8)
C230.073 (11)0.074 (8)0.080 (7)0.014 (6)0.006 (6)0.006 (6)
C240.061 (7)0.147 (16)0.45 (4)0.015 (9)0.011 (16)0.18 (2)
C250.047 (5)0.22 (2)0.188 (17)0.019 (10)0.015 (7)0.060 (15)
C260.084 (9)0.219 (19)0.123 (10)0.061 (9)0.050 (7)0.055 (9)
C23A0.030 (3)0.090 (5)0.142 (6)0.003 (2)0.014 (3)0.017 (4)
C24A0.053 (3)0.128 (5)0.205 (6)0.025 (3)0.006 (3)0.040 (5)
C25A0.088 (4)0.147 (6)0.171 (7)0.024 (4)0.059 (4)0.040 (4)
C26A0.042 (3)0.241 (12)0.408 (19)0.021 (4)0.054 (6)0.188 (12)
N10.0468 (7)0.0547 (7)0.0524 (7)0.0020 (6)0.0054 (5)0.0013 (6)
O10.0477 (7)0.0630 (7)0.1038 (10)0.0065 (6)0.0081 (6)0.0083 (6)
O20.0398 (7)0.0966 (11)0.1572 (15)0.0006 (7)0.0143 (8)0.0054 (10)
O30.0654 (9)0.0876 (10)0.1213 (12)0.0021 (7)0.0049 (8)0.0322 (9)
Geometric parameters (Å, º) top
C1—C61.348 (2)C18—H180.9300
C1—C21.486 (2)C19—H190.9300
C1—C51.496 (2)C20—O21.412 (3)
C2—O11.2242 (18)C20—H20A0.9600
C2—C31.494 (2)C20—H20B0.9600
C3—C131.341 (2)C20—H20C0.9600
C3—C41.495 (2)C21—O31.424 (2)
C4—N11.4538 (18)C21—H21A0.9600
C4—H4A0.9700C21—H21B0.9600
C4—H4B0.9700C21—H21C0.9600
C5—N11.460 (2)C22—N11.450 (2)
C5—H5A0.9700C22—H22A0.9600
C5—H5B0.9700C22—H22B0.9600
C6—C71.466 (2)C22—H22C0.9600
C6—H60.9300C23—C261.521 (9)
C7—C81.392 (2)C23—C241.524 (9)
C7—C121.394 (2)C23—C251.536 (9)
C8—C91.383 (2)C24—H24A0.9600
C8—H80.9300C24—H24B0.9600
C9—O21.368 (2)C24—H24C0.9600
C9—C101.377 (3)C25—H25A0.9600
C10—C111.378 (3)C25—H25B0.9600
C10—H100.9300C25—H25C0.9600
C11—O31.365 (2)C26—H26A0.9600
C11—C121.380 (2)C26—H26B0.9600
C12—H120.9300C26—H26C0.9600
C13—C141.466 (2)C23A—C24A1.508 (7)
C13—H130.9300C23A—C25A1.512 (7)
C14—C151.386 (2)C23A—C26A1.518 (7)
C14—C191.390 (2)C24A—H24D0.9600
C15—C161.381 (2)C24A—H24E0.9600
C15—H150.9300C24A—H24F0.9600
C16—C171.375 (3)C25A—H25D0.9600
C16—H160.9300C25A—H25E0.9600
C17—C181.381 (2)C25A—H25F0.9600
C17—C231.447 (17)C26A—H26D0.9600
C17—C23A1.566 (8)C26A—H26E0.9600
C18—C191.383 (2)C26A—H26F0.9600
C6—C1—C2117.26 (15)O2—C20—H20C109.5
C6—C1—C5124.67 (15)H20A—C20—H20C109.5
C2—C1—C5118.04 (13)H20B—C20—H20C109.5
O1—C2—C1121.40 (14)O3—C21—H21A109.5
O1—C2—C3120.91 (14)O3—C21—H21B109.5
C1—C2—C3117.69 (14)H21A—C21—H21B109.5
C13—C3—C2117.53 (14)O3—C21—H21C109.5
C13—C3—C4124.71 (14)H21A—C21—H21C109.5
C2—C3—C4117.75 (13)H21B—C21—H21C109.5
N1—C4—C3111.15 (12)N1—C22—H22A109.5
N1—C4—H4A109.4N1—C22—H22B109.5
C3—C4—H4A109.4H22A—C22—H22B109.5
N1—C4—H4B109.4N1—C22—H22C109.5
C3—C4—H4B109.4H22A—C22—H22C109.5
H4A—C4—H4B108.0H22B—C22—H22C109.5
N1—C5—C1112.77 (13)C17—C23—C26120.9 (12)
N1—C5—H5A109.0C17—C23—C24114.9 (12)
C1—C5—H5A109.0C26—C23—C24104.2 (16)
N1—C5—H5B109.0C17—C23—C25109.7 (9)
C1—C5—H5B109.0C26—C23—C2598.7 (15)
H5A—C5—H5B107.8C24—C23—C25106.5 (15)
C1—C6—C7129.33 (17)C23—C24—H24A109.5
C1—C6—H6115.3C23—C24—H24B109.5
C7—C6—H6115.3H24A—C24—H24B109.5
C8—C7—C12119.08 (16)C23—C24—H24C109.5
C8—C7—C6117.23 (16)H24A—C24—H24C109.5
C12—C7—C6123.68 (15)H24B—C24—H24C109.5
C9—C8—C7120.04 (18)C23—C25—H25A109.5
C9—C8—H8120.0C23—C25—H25B109.5
C7—C8—H8120.0H25A—C25—H25B109.5
O2—C9—C10114.72 (16)C23—C25—H25C109.5
O2—C9—C8124.78 (18)H25A—C25—H25C109.5
C10—C9—C8120.50 (17)H25B—C25—H25C109.5
C9—C10—C11119.73 (17)C23—C26—H26A109.5
C9—C10—H10120.1C23—C26—H26B109.5
C11—C10—H10120.1H26A—C26—H26B109.5
O3—C11—C10115.06 (17)C23—C26—H26C109.5
O3—C11—C12124.36 (17)H26A—C26—H26C109.5
C10—C11—C12120.57 (18)H26B—C26—H26C109.5
C11—C12—C7120.04 (16)C24A—C23A—C25A108.6 (6)
C11—C12—H12120.0C24A—C23A—C26A110.0 (9)
C7—C12—H12120.0C25A—C23A—C26A114.0 (7)
C3—C13—C14130.18 (15)C24A—C23A—C17109.3 (5)
C3—C13—H13114.9C25A—C23A—C17108.0 (5)
C14—C13—H13114.9C26A—C23A—C17106.9 (6)
C15—C14—C19116.48 (15)C23A—C24A—H24D109.5
C15—C14—C13118.36 (14)C23A—C24A—H24E109.5
C19—C14—C13125.00 (14)H24D—C24A—H24E109.5
C16—C15—C14121.78 (16)C23A—C24A—H24F109.5
C16—C15—H15119.1H24D—C24A—H24F109.5
C14—C15—H15119.1H24E—C24A—H24F109.5
C17—C16—C15121.89 (17)C23A—C25A—H25D109.5
C17—C16—H16119.1C23A—C25A—H25E109.5
C15—C16—H16119.1H25D—C25A—H25E109.5
C16—C17—C18116.49 (16)C23A—C25A—H25F109.5
C16—C17—C23124.9 (6)H25D—C25A—H25F109.5
C18—C17—C23118.5 (6)H25E—C25A—H25F109.5
C16—C17—C23A120.6 (3)C23A—C26A—H26D109.5
C18—C17—C23A122.9 (3)C23A—C26A—H26E109.5
C17—C18—C19122.34 (17)H26D—C26A—H26E109.5
C17—C18—H18118.8C23A—C26A—H26F109.5
C19—C18—H18118.8H26D—C26A—H26F109.5
C18—C19—C14120.99 (16)H26E—C26A—H26F109.5
C18—C19—H19119.5C22—N1—C4109.69 (13)
C14—C19—H19119.5C22—N1—C5109.76 (13)
O2—C20—H20A109.5C4—N1—C5110.35 (12)
O2—C20—H20B109.5C9—O2—C20117.88 (16)
H20A—C20—H20B109.5C11—O3—C21117.76 (16)
C6—C1—C2—O16.9 (2)C19—C14—C15—C161.9 (3)
C5—C1—C2—O1171.41 (15)C13—C14—C15—C16177.61 (18)
C6—C1—C2—C3173.30 (14)C14—C15—C16—C171.2 (3)
C5—C1—C2—C38.4 (2)C15—C16—C17—C180.0 (3)
O1—C2—C3—C134.1 (2)C15—C16—C17—C23176.4 (6)
C1—C2—C3—C13176.02 (13)C15—C16—C17—C23A179.6 (4)
O1—C2—C3—C4175.73 (14)C16—C17—C18—C190.4 (3)
C1—C2—C3—C44.1 (2)C23—C17—C18—C19177.0 (6)
C13—C3—C4—N1148.83 (14)C23A—C17—C18—C19180.0 (4)
C2—C3—C4—N131.04 (18)C17—C18—C19—C140.4 (3)
C6—C1—C5—N1155.52 (15)C15—C14—C19—C181.5 (3)
C2—C1—C5—N122.62 (19)C13—C14—C19—C18176.88 (17)
C2—C1—C6—C7178.52 (15)C16—C17—C23—C26128.0 (14)
C5—C1—C6—C70.4 (3)C18—C17—C23—C2648.4 (16)
C1—C6—C7—C8154.72 (17)C16—C17—C23—C242 (2)
C1—C6—C7—C1225.3 (3)C18—C17—C23—C24174.8 (19)
C12—C7—C8—C91.9 (3)C16—C17—C23—C25118.3 (16)
C6—C7—C8—C9178.09 (16)C18—C17—C23—C2565.3 (18)
C7—C8—C9—O2179.37 (18)C16—C17—C23A—C24A36.1 (8)
C7—C8—C9—C100.5 (3)C18—C17—C23A—C24A143.5 (5)
O2—C9—C10—C11179.39 (18)C16—C17—C23A—C25A81.9 (7)
C8—C9—C10—C110.7 (3)C18—C17—C23A—C25A98.5 (6)
C9—C10—C11—O3178.68 (17)C16—C17—C23A—C26A155.1 (9)
C9—C10—C11—C120.5 (3)C18—C17—C23A—C26A24.5 (9)
O3—C11—C12—C7179.98 (17)C3—C4—N1—C22175.71 (13)
C10—C11—C12—C70.9 (3)C3—C4—N1—C563.25 (16)
C8—C7—C12—C112.1 (3)C1—C5—N1—C22179.78 (13)
C6—C7—C12—C11177.91 (16)C1—C5—N1—C459.22 (17)
C2—C3—C13—C14176.06 (15)C10—C9—O2—C20162.1 (2)
C4—C3—C13—C144.1 (3)C8—C9—O2—C2018.0 (3)
C3—C13—C14—C15162.00 (17)C10—C11—O3—C21175.3 (2)
C3—C13—C14—C1922.7 (3)C12—C11—O3—C215.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26A—H26F···O2i0.962.753.554 (12)141
C22—H22B···O1ii0.962.863.429 (2)119
Symmetry codes: (i) x1, y+3/2, z1/2; (ii) x, y+3/2, z1/2.
(5E)-3-{3-[(E)-(2,3-Dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one (exp_2476) top
Crystal data top
C27H23FN2O3Z = 2
Mr = 442.47F(000) = 464
Triclinic, P1Dx = 1.334 Mg m3
a = 7.0689 (5) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.2072 (5) ÅCell parameters from 2081 reflections
c = 20.1397 (16) Åθ = 7.5–69.2°
α = 94.401 (6)°µ = 0.76 mm1
β = 97.829 (6)°T = 293 K
γ = 106.575 (6)°Plate, clear light bronze
V = 1101.18 (14) Å30.20 × 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 tube2886 reflections with I > 2σ(I)
Detector resolution: 8.22 pixels mm-1Rint = 0.027
ω scansθmax = 71.0°, θmin = 4.5°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 88
Tmin = 0.917, Tmax = 1.000k = 96
7150 measured reflectionsl = 1924
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-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 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
C10.2270 (3)0.2496 (3)0.76231 (10)0.0560 (5)
C20.2252 (3)0.1517 (3)0.69695 (10)0.0574 (5)
C30.4174 (3)0.1906 (3)0.66868 (11)0.0621 (5)
H3A0.49450.11710.68510.075*
H3B0.38780.16810.61980.075*
C40.5997 (3)0.3963 (3)0.76189 (9)0.0555 (5)
H4A0.68740.51230.77510.067*
H4B0.67460.31790.77450.067*
C50.4224 (3)0.3675 (2)0.79797 (9)0.0517 (4)
C60.0524 (3)0.0373 (3)0.66718 (11)0.0669 (6)
H60.05570.03240.68940.080*
C70.0072 (4)0.0812 (3)0.60512 (11)0.0709 (6)
C80.1871 (5)0.1395 (4)0.57069 (13)0.0918 (8)
C90.2464 (6)0.2508 (4)0.51297 (16)0.1186 (12)
H90.37990.28700.49240.142*
C100.1096 (8)0.3085 (4)0.48576 (17)0.1295 (15)
H100.14700.38160.44550.155*
C110.0855 (7)0.2578 (4)0.51830 (17)0.1190 (12)
H110.17960.29930.50040.143*
C120.1434 (5)0.1460 (3)0.57746 (14)0.0932 (8)
H120.27590.11400.59890.112*
C130.4239 (3)0.4449 (2)0.85882 (9)0.0529 (4)
H130.29950.42320.87240.064*
C140.5907 (3)0.5585 (2)0.90749 (9)0.0502 (4)
C150.5489 (2)0.6679 (2)0.95580 (9)0.0508 (4)
H150.41760.67030.95410.061*
C160.6949 (3)0.7734 (2)1.00643 (9)0.0502 (4)
C170.8914 (3)0.7676 (3)1.00944 (10)0.0589 (5)
H170.99200.83591.04320.071*
C180.9348 (3)0.6604 (3)0.96222 (10)0.0622 (5)
H181.06630.65830.96430.075*
C190.7894 (3)0.5553 (3)0.91160 (10)0.0563 (5)
H190.82310.48300.88050.068*
C200.7547 (3)0.9895 (2)1.09784 (10)0.0544 (5)
H200.89021.01901.09490.065*
C210.6905 (3)1.0785 (2)1.15058 (9)0.0513 (4)
C220.4890 (2)1.0333 (2)1.15879 (9)0.0506 (4)
C230.4332 (3)1.1183 (2)1.21175 (10)0.0563 (5)
C240.5736 (3)1.2464 (3)1.25530 (11)0.0627 (5)
H240.53491.30201.29070.075*
C250.7720 (3)1.2933 (3)1.24698 (12)0.0688 (6)
H250.86611.38131.27620.083*
C260.8297 (3)1.2095 (3)1.19545 (11)0.0634 (5)
H260.96361.24061.19030.076*
C270.7062 (3)0.4162 (4)0.65468 (11)0.0833 (7)
H27A0.79120.34640.66620.125*
H27B0.77940.53460.66850.125*
H27C0.66210.39880.60670.125*
F10.3275 (3)0.0814 (3)0.59540 (10)0.1439 (8)
N10.5334 (2)0.3691 (2)0.68888 (8)0.0581 (4)
N20.6306 (2)0.8707 (2)1.05465 (8)0.0535 (4)
O10.0748 (2)0.2306 (2)0.78767 (8)0.0775 (5)
O20.34485 (18)0.90889 (19)1.11746 (7)0.0647 (4)
H20.39420.86901.08800.097*
O30.2381 (2)1.0789 (2)1.22059 (10)0.0835 (5)
H30.17630.98361.20070.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0451 (9)0.0594 (11)0.0584 (11)0.0086 (8)0.0061 (8)0.0079 (9)
C20.0543 (11)0.0554 (11)0.0575 (11)0.0111 (9)0.0032 (9)0.0075 (9)
C30.0575 (11)0.0668 (13)0.0587 (12)0.0162 (10)0.0067 (9)0.0025 (10)
C40.0454 (9)0.0649 (12)0.0507 (10)0.0101 (9)0.0036 (8)0.0071 (9)
C50.0425 (9)0.0571 (11)0.0518 (10)0.0106 (8)0.0030 (7)0.0086 (8)
C60.0602 (12)0.0691 (13)0.0594 (12)0.0039 (10)0.0047 (9)0.0044 (10)
C70.0807 (14)0.0568 (13)0.0590 (12)0.0005 (11)0.0004 (11)0.0057 (10)
C80.0927 (19)0.0898 (19)0.0680 (15)0.0004 (15)0.0060 (14)0.0016 (14)
C90.144 (3)0.101 (2)0.0722 (19)0.001 (2)0.0284 (19)0.0048 (17)
C100.213 (5)0.074 (2)0.0698 (19)0.014 (3)0.013 (2)0.0084 (15)
C110.181 (4)0.0757 (19)0.096 (2)0.039 (2)0.018 (2)0.0132 (17)
C120.116 (2)0.0678 (15)0.0877 (18)0.0232 (15)0.0082 (16)0.0056 (14)
C130.0430 (9)0.0597 (11)0.0531 (11)0.0105 (8)0.0058 (8)0.0109 (9)
C140.0426 (9)0.0589 (11)0.0469 (9)0.0109 (8)0.0058 (7)0.0131 (8)
C150.0370 (8)0.0642 (11)0.0499 (10)0.0126 (8)0.0051 (7)0.0122 (9)
C160.0428 (9)0.0596 (11)0.0464 (9)0.0117 (8)0.0057 (7)0.0114 (8)
C170.0413 (9)0.0712 (13)0.0576 (11)0.0116 (9)0.0011 (8)0.0051 (10)
C180.0400 (9)0.0826 (14)0.0629 (12)0.0193 (9)0.0034 (8)0.0073 (11)
C190.0461 (9)0.0687 (12)0.0549 (11)0.0188 (9)0.0067 (8)0.0090 (9)
C200.0392 (9)0.0594 (11)0.0616 (11)0.0089 (8)0.0091 (8)0.0099 (9)
C210.0413 (9)0.0526 (10)0.0571 (10)0.0108 (8)0.0041 (8)0.0090 (8)
C220.0387 (8)0.0515 (10)0.0570 (10)0.0086 (8)0.0015 (7)0.0087 (9)
C230.0443 (9)0.0557 (11)0.0699 (12)0.0146 (8)0.0111 (9)0.0113 (10)
C240.0619 (12)0.0553 (12)0.0701 (13)0.0188 (10)0.0084 (10)0.0017 (10)
C250.0552 (11)0.0574 (12)0.0833 (15)0.0112 (10)0.0032 (10)0.0070 (11)
C260.0415 (9)0.0600 (12)0.0798 (14)0.0068 (9)0.0024 (9)0.0009 (11)
C270.0636 (13)0.110 (2)0.0613 (13)0.0016 (13)0.0153 (10)0.0053 (13)
F10.0777 (11)0.196 (2)0.1196 (15)0.0102 (12)0.0175 (10)0.0350 (14)
N10.0495 (8)0.0659 (10)0.0512 (9)0.0063 (7)0.0056 (7)0.0069 (8)
N20.0440 (8)0.0626 (10)0.0511 (8)0.0128 (7)0.0046 (6)0.0083 (7)
O10.0467 (7)0.0905 (11)0.0807 (10)0.0032 (7)0.0116 (7)0.0136 (9)
O20.0396 (6)0.0729 (9)0.0702 (9)0.0058 (6)0.0019 (6)0.0051 (7)
O30.0527 (8)0.0830 (11)0.1097 (14)0.0099 (8)0.0289 (9)0.0068 (10)
Geometric parameters (Å, º) top
C1—O11.228 (2)C15—C161.386 (2)
C1—C21.485 (3)C15—H150.9300
C1—C51.490 (2)C16—C171.397 (2)
C2—C61.339 (3)C16—N21.413 (2)
C2—C31.504 (3)C17—C181.370 (3)
C3—N11.454 (2)C17—H170.9300
C3—H3A0.9700C18—C191.383 (3)
C3—H3B0.9700C18—H180.9300
C4—N11.461 (2)C19—H190.9300
C4—C51.504 (2)C20—N21.285 (2)
C4—H4A0.9700C20—C211.438 (3)
C4—H4B0.9700C20—H200.9300
C5—C131.334 (3)C21—C261.395 (3)
C6—C71.462 (3)C21—C221.402 (2)
C6—H60.9300C22—O21.349 (2)
C7—C81.382 (3)C22—C231.392 (3)
C7—C121.383 (4)C23—O31.363 (2)
C8—F11.352 (4)C23—C241.373 (3)
C8—C91.359 (4)C24—C251.382 (3)
C9—C101.351 (5)C24—H240.9300
C9—H90.9300C25—C261.371 (3)
C10—C111.374 (5)C25—H250.9300
C10—H100.9300C26—H260.9300
C11—C121.384 (4)C27—N11.455 (3)
C11—H110.9300C27—H27A0.9600
C12—H120.9300C27—H27B0.9600
C13—C141.462 (2)C27—H27C0.9600
C13—H130.9300O2—H20.8200
C14—C151.391 (3)O3—H30.8200
C14—C191.404 (2)
O1—C1—C2121.63 (18)C16—C15—C14122.73 (16)
O1—C1—C5120.61 (18)C16—C15—H15118.6
C2—C1—C5117.72 (17)C14—C15—H15118.6
C6—C2—C1117.68 (19)C15—C16—C17118.46 (18)
C6—C2—C3124.9 (2)C15—C16—N2117.02 (15)
C1—C2—C3117.39 (17)C17—C16—N2124.35 (17)
N1—C3—C2110.07 (17)C18—C17—C16119.45 (18)
N1—C3—H3A109.6C18—C17—H17120.3
C2—C3—H3A109.6C16—C17—H17120.3
N1—C3—H3B109.6C17—C18—C19122.18 (17)
C2—C3—H3B109.6C17—C18—H18118.9
H3A—C3—H3B108.2C19—C18—H18118.9
N1—C4—C5110.19 (15)C18—C19—C14119.50 (19)
N1—C4—H4A109.6C18—C19—H19120.2
C5—C4—H4A109.6C14—C19—H19120.2
N1—C4—H4B109.6N2—C20—C21122.05 (16)
C5—C4—H4B109.6N2—C20—H20119.0
H4A—C4—H4B108.1C21—C20—H20119.0
C13—C5—C1116.90 (17)C26—C21—C22118.86 (18)
C13—C5—C4124.98 (17)C26—C21—C20120.18 (17)
C1—C5—C4118.07 (17)C22—C21—C20120.95 (17)
C2—C6—C7130.0 (2)O2—C22—C23117.92 (16)
C2—C6—H6115.0O2—C22—C21122.65 (18)
C7—C6—H6115.0C23—C22—C21119.43 (17)
C8—C7—C12115.4 (2)O3—C23—C24118.72 (19)
C8—C7—C6119.1 (3)O3—C23—C22120.85 (18)
C12—C7—C6125.4 (2)C24—C23—C22120.41 (17)
F1—C8—C9117.6 (3)C23—C24—C25120.5 (2)
F1—C8—C7118.2 (2)C23—C24—H24119.8
C9—C8—C7124.2 (3)C25—C24—H24119.8
C10—C9—C8119.4 (4)C26—C25—C24119.8 (2)
C10—C9—H9120.3C26—C25—H25120.1
C8—C9—H9120.3C24—C25—H25120.1
C9—C10—C11119.2 (3)C25—C26—C21121.01 (18)
C9—C10—H10120.4C25—C26—H26119.5
C11—C10—H10120.4C21—C26—H26119.5
C10—C11—C12120.8 (4)N1—C27—H27A109.5
C10—C11—H11119.6N1—C27—H27B109.5
C12—C11—H11119.6H27A—C27—H27B109.5
C7—C12—C11121.0 (3)N1—C27—H27C109.5
C7—C12—H12119.5H27A—C27—H27C109.5
C11—C12—H12119.5H27B—C27—H27C109.5
C5—C13—C14130.11 (18)C3—N1—C27111.12 (18)
C5—C13—H13114.9C3—N1—C4109.22 (16)
C14—C13—H13114.9C27—N1—C4109.67 (15)
C15—C14—C19117.67 (17)C20—N2—C16122.06 (15)
C15—C14—C13118.32 (16)C22—O2—H2109.5
C19—C14—C13123.84 (18)C23—O3—H3109.5
O1—C1—C2—C62.0 (3)C13—C14—C15—C16176.28 (16)
C5—C1—C2—C6175.59 (17)C14—C15—C16—C170.9 (3)
O1—C1—C2—C3177.15 (19)C14—C15—C16—N2176.31 (16)
C5—C1—C2—C35.3 (3)C15—C16—C17—C180.8 (3)
C6—C2—C3—N1148.4 (2)N2—C16—C17—C18175.89 (18)
C1—C2—C3—N130.7 (2)C16—C17—C18—C190.8 (3)
O1—C1—C5—C132.3 (3)C17—C18—C19—C140.7 (3)
C2—C1—C5—C13175.28 (17)C15—C14—C19—C180.7 (3)
O1—C1—C5—C4175.10 (19)C13—C14—C19—C18175.86 (18)
C2—C1—C5—C47.3 (3)N2—C20—C21—C26178.46 (18)
N1—C4—C5—C13150.57 (19)N2—C20—C21—C222.8 (3)
N1—C4—C5—C126.6 (2)C26—C21—C22—O2179.61 (18)
C1—C2—C6—C7177.2 (2)C20—C21—C22—O21.6 (3)
C3—C2—C6—C73.8 (4)C26—C21—C22—C230.8 (3)
C2—C6—C7—C8155.8 (2)C20—C21—C22—C23177.90 (17)
C2—C6—C7—C1226.0 (4)O2—C22—C23—O31.2 (3)
C12—C7—C8—F1179.7 (3)C21—C22—C23—O3179.18 (18)
C6—C7—C8—F11.2 (4)O2—C22—C23—C24179.85 (17)
C12—C7—C8—C90.9 (4)C21—C22—C23—C240.6 (3)
C6—C7—C8—C9179.4 (3)O3—C23—C24—C25178.3 (2)
F1—C8—C9—C10178.4 (3)C22—C23—C24—C250.3 (3)
C7—C8—C9—C101.0 (5)C23—C24—C25—C261.0 (3)
C8—C9—C10—C112.2 (6)C24—C25—C26—C210.7 (3)
C9—C10—C11—C121.5 (5)C22—C21—C26—C250.2 (3)
C8—C7—C12—C111.7 (4)C20—C21—C26—C25178.56 (19)
C6—C7—C12—C11180.0 (2)C2—C3—N1—C27172.11 (17)
C10—C11—C12—C70.5 (5)C2—C3—N1—C466.8 (2)
C1—C5—C13—C14176.21 (18)C5—C4—N1—C364.5 (2)
C4—C5—C13—C146.6 (3)C5—C4—N1—C27173.51 (18)
C5—C13—C14—C15158.11 (19)C21—C20—N2—C16174.52 (16)
C5—C13—C14—C1926.7 (3)C15—C16—N2—C20170.10 (17)
C19—C14—C15—C160.8 (3)C17—C16—N2—C2014.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.822.332.723 (2)110
O2—H2···N20.821.882.603 (2)146
C17—H17···O2i0.932.613.456 (2)152
C12—H12···F1i0.932.753.588 (4)150
O3—H3···O1ii0.822.172.829 (2)138
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z+2.
Cytotoxicity activities of (5), (6) and (12) presented as IC50M) top
CompoundIC50M)
HepG2THP-1LO2
(5)4.24±0.613.15±0.2316.18±1.39
(6)10.32±0.188.66±0.8227.21±0.95
(12)2.86±0.052.54±0.3212.3±0.26
Curcumin13.78±0.3122.54±0.3425.67±0.23
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds