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The syntheses of nine new 5-iodo­salicylic acid-based 1,3,4-oxa­diazo­line derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitro­phen­yl)-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitro­phen­yl)-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl)-4-iodo­phenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluoro­phen­yl)-5-methyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chloro­phen­yl)-5-methyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromo­phen­yl)-5-methyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6f), 2-[4-acetyl-5-(4-bromo­phen­yl)-5-methyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methyl­phen­yl)-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6h) and 2-[5-(4-acetamido­phen­yl)-4-acetyl-5-methyl-4,5-di­hydro-1,3,4-oxa­diazol-2-yl]-4-iodo­phenyl acetate (6i). The compounds were characterized by mass, 1H NMR and 13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxa­diazo­line ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H...O, C—H...π and I...π inter­actions. For 6e, the 1,3,4-oxa­diazo­line ring is almost planar. In the packing, Cl...π inter­actions are observed, while the I atom is not involved in short inter­actions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9–4.5 µM.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618008719/sk3693sup1.cif
Contains datablocks global, 6d, 6e, 6c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936csup2.hkl
Contains datablock 6c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936dsup3.hkl
Contains datablock 6d

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008719/sk36936esup4.hkl
Contains datablock 6e

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936csup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936dsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008719/sk36936esup7.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618008719/sk3693sup8.pdf
NMR spectra

CCDC references: 1849175; 1849174; 1849173

Computing details top

For all structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (6c), (6e); SHELXT (Sheldrick, 2015a) for (6d). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-(4-Acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate (6c) top
Crystal data top
C19H17IN2O4F(000) = 920
Mr = 464.24Dx = 1.683 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.837 (1) ÅCell parameters from 9773 reflections
b = 20.056 (1) Åθ = 3.2–33.1°
c = 11.015 (1) ŵ = 1.77 mm1
β = 110.18 (1)°T = 100 K
V = 1832.4 (3) Å3Block, colourless
Z = 40.42 × 0.20 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
4994 reflections with I > 2σ(I)
φ and ω scansRint = 0.029
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 30.5°, θmin = 2.8°
Tmin = 0.627, Tmax = 0.747h = 1212
54289 measured reflectionsk = 2828
5600 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0212P)2 + 1.2207P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
5600 reflectionsΔρmax = 0.97 e Å3
238 parametersΔρmin = 0.59 e Å3
0 restraints
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
I11.02273 (2)0.44378 (2)0.71043 (2)0.02391 (4)
O10.42189 (12)0.51004 (5)0.22300 (10)0.0198 (2)
N10.44105 (14)0.63918 (6)0.32433 (11)0.0172 (2)
C10.81918 (17)0.46520 (7)0.54844 (14)0.0185 (3)
O20.57214 (14)0.56173 (6)0.12194 (11)0.0265 (2)
N20.43632 (14)0.70564 (6)0.36222 (11)0.0170 (2)
C20.75217 (17)0.52839 (7)0.53642 (13)0.0177 (3)
H20.7953970.5603190.6031410.021*
O30.63889 (13)0.65492 (5)0.51584 (9)0.0191 (2)
C30.62097 (16)0.54536 (7)0.42630 (13)0.0162 (2)
O40.31986 (13)0.80687 (5)0.32597 (11)0.0240 (2)
C40.55900 (17)0.49706 (7)0.33034 (13)0.0175 (3)
C50.62622 (19)0.43404 (7)0.34230 (15)0.0221 (3)
H50.5829600.4019210.2759600.027*
C60.75733 (19)0.41777 (7)0.45167 (15)0.0226 (3)
H60.8042380.3746280.4602110.027*
C70.55901 (16)0.61343 (7)0.41634 (13)0.0161 (2)
C80.58015 (17)0.72191 (7)0.47773 (13)0.0165 (2)
C90.70562 (16)0.76014 (7)0.43953 (13)0.0170 (2)
C100.82350 (18)0.72550 (8)0.40745 (15)0.0225 (3)
H100.8289010.6782810.4144480.027*
C110.93294 (19)0.75959 (9)0.36537 (16)0.0289 (3)
H111.0128290.7355240.3439170.035*
C120.92662 (19)0.82828 (9)0.35443 (16)0.0294 (3)
H121.0010080.8513590.3246780.035*
C130.8109 (2)0.86321 (9)0.38721 (17)0.0299 (3)
H130.8065160.9104370.3802230.036*
C140.70118 (18)0.82959 (8)0.43030 (15)0.0235 (3)
H140.6230570.8539660.4534850.028*
C150.44235 (18)0.54575 (7)0.12345 (14)0.0197 (3)
C160.2830 (2)0.55892 (8)0.02103 (15)0.0274 (3)
H16A0.2457720.5185320.0307770.041*
H16B0.2941260.5951760.0349300.041*
H16C0.2044760.5716870.0615920.041*
C170.5379 (2)0.75217 (8)0.58752 (14)0.0236 (3)
H17A0.4569480.7243540.6056010.035*
H17B0.4943000.7970930.5632470.035*
H17C0.6348960.7546920.6649220.035*
C180.31788 (16)0.74827 (7)0.29343 (13)0.0176 (3)
C190.18862 (18)0.71930 (8)0.17778 (15)0.0227 (3)
H19A0.1016670.7519070.1436040.034*
H19B0.1455360.6787580.2034690.034*
H19C0.2344310.7083410.1109140.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02366 (5)0.02116 (5)0.02296 (5)0.00370 (3)0.00299 (4)0.00274 (3)
O10.0188 (5)0.0201 (5)0.0183 (5)0.0032 (4)0.0038 (4)0.0003 (4)
N10.0175 (5)0.0151 (5)0.0192 (5)0.0000 (4)0.0065 (4)0.0022 (4)
C10.0184 (6)0.0178 (6)0.0192 (6)0.0005 (5)0.0064 (5)0.0028 (5)
O20.0257 (6)0.0309 (6)0.0238 (5)0.0008 (4)0.0096 (4)0.0042 (4)
N20.0163 (5)0.0159 (5)0.0175 (5)0.0010 (4)0.0041 (4)0.0023 (4)
C20.0192 (6)0.0171 (6)0.0173 (6)0.0010 (5)0.0070 (5)0.0001 (5)
O30.0241 (5)0.0154 (5)0.0148 (4)0.0027 (4)0.0029 (4)0.0007 (4)
C30.0167 (6)0.0158 (6)0.0175 (6)0.0008 (5)0.0078 (5)0.0003 (5)
O40.0233 (5)0.0190 (5)0.0290 (5)0.0038 (4)0.0083 (4)0.0007 (4)
C40.0173 (6)0.0180 (6)0.0172 (6)0.0026 (5)0.0060 (5)0.0009 (5)
C50.0257 (7)0.0166 (7)0.0230 (7)0.0025 (5)0.0070 (6)0.0029 (5)
C60.0263 (7)0.0145 (6)0.0264 (7)0.0014 (5)0.0082 (6)0.0002 (5)
C70.0177 (6)0.0165 (6)0.0151 (6)0.0008 (5)0.0068 (5)0.0013 (5)
C80.0182 (6)0.0165 (6)0.0141 (6)0.0028 (5)0.0046 (5)0.0010 (5)
C90.0162 (6)0.0197 (6)0.0133 (6)0.0008 (5)0.0028 (5)0.0022 (5)
C100.0198 (7)0.0243 (7)0.0235 (7)0.0021 (5)0.0077 (5)0.0033 (6)
C110.0195 (7)0.0388 (9)0.0304 (8)0.0001 (6)0.0111 (6)0.0033 (7)
C120.0201 (7)0.0400 (9)0.0272 (8)0.0065 (6)0.0071 (6)0.0020 (7)
C130.0276 (8)0.0243 (8)0.0361 (9)0.0043 (6)0.0090 (7)0.0014 (7)
C140.0214 (7)0.0208 (7)0.0279 (7)0.0015 (5)0.0080 (6)0.0018 (6)
C150.0245 (7)0.0168 (6)0.0169 (6)0.0003 (5)0.0058 (5)0.0021 (5)
C160.0264 (8)0.0299 (8)0.0206 (7)0.0022 (6)0.0014 (6)0.0003 (6)
C170.0307 (8)0.0251 (7)0.0179 (6)0.0042 (6)0.0122 (6)0.0020 (5)
C180.0149 (6)0.0204 (6)0.0195 (6)0.0017 (5)0.0085 (5)0.0026 (5)
C190.0162 (6)0.0265 (7)0.0231 (7)0.0008 (5)0.0040 (5)0.0013 (6)
Geometric parameters (Å, º) top
I1—C12.0951 (14)C9—C101.395 (2)
O1—C41.3948 (17)C9—C141.396 (2)
O1—C151.3727 (17)C10—H100.9500
N1—N21.4017 (16)C10—C111.388 (2)
N1—C71.2851 (18)C11—H110.9500
C1—C21.386 (2)C11—C121.382 (3)
C1—C61.392 (2)C12—H120.9500
O2—C151.1966 (19)C12—C131.386 (2)
N2—C81.4917 (18)C13—H130.9500
N2—C181.3614 (18)C13—C141.392 (2)
C2—H20.9500C14—H140.9500
C2—C31.4004 (19)C15—C161.493 (2)
O3—C71.3631 (16)C16—H16A0.9800
O3—C81.4493 (16)C16—H16B0.9800
C3—C41.3986 (19)C16—H16C0.9800
C3—C71.4610 (19)C17—H17A0.9800
O4—C181.2270 (18)C17—H17B0.9800
C4—C51.383 (2)C17—H17C0.9800
C5—H50.9500C18—C191.504 (2)
C5—C61.392 (2)C19—H19A0.9800
C6—H60.9500C19—H19B0.9800
C8—C91.522 (2)C19—H19C0.9800
C8—C171.5107 (19)
C15—O1—C4117.34 (11)C11—C10—H10119.8
C7—N1—N2104.29 (11)C10—C11—H11119.7
C2—C1—I1118.81 (10)C12—C11—C10120.55 (15)
C2—C1—C6120.65 (13)C12—C11—H11119.7
C6—C1—I1120.47 (11)C11—C12—H12120.3
N1—N2—C8110.97 (11)C11—C12—C13119.49 (15)
C18—N2—N1121.85 (12)C13—C12—H12120.3
C18—N2—C8127.06 (12)C12—C13—H13119.8
C1—C2—H2119.9C12—C13—C14120.47 (16)
C1—C2—C3120.26 (13)C14—C13—H13119.8
C3—C2—H2119.9C9—C14—H14119.9
C7—O3—C8107.38 (10)C13—C14—C9120.17 (15)
C2—C3—C7117.97 (12)C13—C14—H14119.9
C4—C3—C2118.53 (13)O1—C15—C16110.24 (13)
C4—C3—C7123.48 (13)O2—C15—O1122.81 (13)
O1—C4—C3120.69 (12)O2—C15—C16126.93 (14)
C5—C4—O1118.05 (12)C15—C16—H16A109.5
C5—C4—C3121.16 (13)C15—C16—H16B109.5
C4—C5—H5120.0C15—C16—H16C109.5
C4—C5—C6119.91 (14)H16A—C16—H16B109.5
C6—C5—H5120.0H16A—C16—H16C109.5
C1—C6—H6120.3H16B—C16—H16C109.5
C5—C6—C1119.49 (14)C8—C17—H17A109.5
C5—C6—H6120.3C8—C17—H17B109.5
N1—C7—O3116.29 (12)C8—C17—H17C109.5
N1—C7—C3128.01 (13)H17A—C17—H17B109.5
O3—C7—C3115.68 (12)H17A—C17—H17C109.5
N2—C8—C9111.22 (11)H17B—C17—H17C109.5
N2—C8—C17113.42 (12)N2—C18—C19116.25 (13)
O3—C8—N299.15 (10)O4—C18—N2120.54 (13)
O3—C8—C9108.96 (11)O4—C18—C19123.21 (13)
O3—C8—C17107.66 (11)C18—C19—H19A109.5
C17—C8—C9115.08 (12)C18—C19—H19B109.5
C10—C9—C8119.86 (13)C18—C19—H19C109.5
C10—C9—C14118.89 (14)H19A—C19—H19B109.5
C14—C9—C8121.19 (13)H19A—C19—H19C109.5
C9—C10—H10119.8H19B—C19—H19C109.5
C11—C10—C9120.41 (15)
I1—C1—C2—C3176.86 (10)C6—C1—C2—C30.0 (2)
I1—C1—C6—C5177.27 (11)C7—N1—N2—C89.02 (14)
O1—C4—C5—C6176.23 (13)C7—N1—N2—C18174.80 (12)
N1—N2—C8—O313.43 (13)C7—O3—C8—N212.66 (13)
N1—N2—C8—C9101.12 (13)C7—O3—C8—C9103.64 (12)
N1—N2—C8—C17127.29 (12)C7—O3—C8—C17130.93 (12)
N1—N2—C18—O4177.27 (12)C7—C3—C4—O16.1 (2)
N1—N2—C18—C192.50 (19)C7—C3—C4—C5177.43 (13)
C1—C2—C3—C40.6 (2)C8—N2—C18—O41.7 (2)
C1—C2—C3—C7177.68 (13)C8—N2—C18—C19178.03 (12)
N2—N1—C7—O30.09 (16)C8—O3—C7—N18.94 (16)
N2—N1—C7—C3178.50 (13)C8—O3—C7—C3169.68 (11)
N2—C8—C9—C1088.99 (15)C8—C9—C10—C11176.32 (14)
N2—C8—C9—C1488.16 (15)C8—C9—C14—C13175.89 (14)
C2—C1—C6—C50.4 (2)C9—C10—C11—C120.1 (2)
C2—C3—C4—O1175.70 (12)C10—C9—C14—C131.3 (2)
C2—C3—C4—C50.8 (2)C10—C11—C12—C130.7 (3)
C2—C3—C7—N1179.85 (14)C11—C12—C13—C140.3 (3)
C2—C3—C7—O31.42 (18)C12—C13—C14—C90.7 (3)
O3—C8—C9—C1019.29 (17)C14—C9—C10—C110.9 (2)
O3—C8—C9—C14163.56 (12)C15—O1—C4—C381.18 (16)
C3—C4—C5—C60.3 (2)C15—O1—C4—C5102.23 (15)
C4—O1—C15—O25.2 (2)C17—C8—C9—C10140.28 (14)
C4—O1—C15—C16176.26 (12)C17—C8—C9—C1442.57 (18)
C4—C3—C7—N11.6 (2)C18—N2—C8—O3170.64 (12)
C4—C3—C7—O3176.80 (12)C18—N2—C8—C974.81 (16)
C4—C5—C6—C10.3 (2)C18—N2—C8—C1756.77 (18)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.513.2828 (19)139
C16—H16B···O4ii0.982.553.529 (2)177
C17—H17C···Cg3iii0.982.703.5766 (17)150
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x, y+3/2, z+1/2.
2-[4-Acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6d) top
Crystal data top
C19H16FIN2O4F(000) = 952
Mr = 482.24Dx = 1.732 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.1241 (4) ÅCell parameters from 9994 reflections
b = 20.0980 (9) Åθ = 2.9–30.5°
c = 10.7456 (5) ŵ = 1.77 mm1
β = 110.224 (2)°T = 100 K
V = 1849.00 (15) Å3Block, colourless
Z = 40.60 × 0.37 × 0.29 mm
Data collection top
Bruker APEXII CCD
diffractometer
3703 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 27.0°, θmin = 2.7°
Tmin = 0.610, Tmax = 0.746h = 1111
52242 measured reflectionsk = 2525
4033 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.047 w = 1/[σ2(Fo2) + (0.0179P)2 + 1.3214P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
4033 reflectionsΔρmax = 0.56 e Å3
247 parametersΔρmin = 0.32 e Å3
0 restraints
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
I11.02927 (2)0.43863 (2)0.70991 (2)0.02562 (5)
F10.99431 (14)0.86573 (7)0.31186 (15)0.0482 (4)
O10.43234 (14)0.50760 (6)0.22482 (12)0.0221 (3)
N10.45186 (17)0.63451 (7)0.33434 (14)0.0196 (3)
C10.8281 (2)0.46130 (9)0.54780 (17)0.0208 (3)
O20.56974 (16)0.56291 (6)0.11907 (14)0.0287 (3)
N20.44708 (17)0.70043 (7)0.37438 (14)0.0193 (3)
C20.7610 (2)0.52365 (8)0.54173 (17)0.0193 (3)
H20.8037740.5545290.6119070.023*
O30.64636 (15)0.64956 (6)0.52903 (12)0.0221 (3)
C30.6303 (2)0.54116 (8)0.43227 (17)0.0185 (3)
O40.33470 (15)0.80138 (6)0.34228 (13)0.0275 (3)
C40.5691 (2)0.49418 (8)0.33133 (17)0.0197 (3)
C50.6368 (2)0.43237 (8)0.33789 (19)0.0244 (4)
H50.5940190.4012130.2682470.029*
C60.7674 (2)0.41554 (9)0.44590 (19)0.0247 (4)
H60.8148350.3731240.4501930.030*
C70.5681 (2)0.60868 (8)0.42603 (16)0.0185 (3)
C80.5860 (2)0.71636 (8)0.49331 (17)0.0197 (3)
C90.7052 (2)0.75722 (8)0.45591 (16)0.0190 (3)
C100.8228 (2)0.72585 (9)0.42326 (19)0.0254 (4)
H100.8352590.6789990.4332280.030*
C110.9221 (2)0.76212 (10)0.3763 (2)0.0327 (4)
H111.0023240.7406750.3537090.039*
C120.9018 (2)0.82967 (10)0.3632 (2)0.0301 (4)
C130.7907 (2)0.86302 (9)0.3985 (2)0.0293 (4)
H130.7814700.9100500.3906990.035*
C140.6923 (2)0.82630 (9)0.44565 (18)0.0242 (4)
H140.6152840.8484650.4713040.029*
C150.4463 (2)0.54563 (9)0.12336 (18)0.0221 (4)
C160.2891 (2)0.55914 (10)0.02252 (19)0.0298 (4)
H16A0.2943830.5990010.0283000.045*
H16B0.2133700.5662580.0673480.045*
H16C0.2564820.5210350.0376650.045*
C170.5423 (2)0.74413 (10)0.60655 (18)0.0274 (4)
H17A0.4632400.7155310.6219140.041*
H17B0.5001120.7891400.5841280.041*
H17C0.6352360.7457180.6869840.041*
C180.3312 (2)0.74345 (9)0.30679 (17)0.0207 (3)
C190.2035 (2)0.71544 (10)0.1893 (2)0.0281 (4)
H19A0.1198640.7483930.1561180.042*
H19B0.1617750.6750410.2157760.042*
H19C0.2455780.7046000.1192750.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02788 (7)0.02021 (7)0.02625 (7)0.00422 (5)0.00614 (5)0.00214 (5)
F10.0294 (6)0.0459 (8)0.0738 (10)0.0073 (6)0.0236 (7)0.0089 (7)
O10.0241 (6)0.0200 (6)0.0208 (6)0.0051 (5)0.0061 (5)0.0002 (5)
N10.0225 (7)0.0160 (7)0.0217 (7)0.0003 (5)0.0094 (6)0.0008 (6)
C10.0221 (8)0.0187 (8)0.0227 (9)0.0002 (7)0.0091 (7)0.0035 (7)
O20.0305 (7)0.0300 (7)0.0275 (7)0.0029 (6)0.0125 (6)0.0043 (6)
N20.0216 (7)0.0172 (7)0.0184 (7)0.0024 (5)0.0062 (6)0.0010 (6)
C20.0240 (9)0.0172 (8)0.0194 (8)0.0015 (6)0.0109 (7)0.0002 (6)
O30.0313 (7)0.0163 (6)0.0156 (6)0.0061 (5)0.0043 (5)0.0008 (5)
C30.0224 (8)0.0170 (8)0.0197 (8)0.0004 (6)0.0118 (7)0.0020 (6)
O40.0282 (7)0.0218 (7)0.0317 (7)0.0070 (5)0.0092 (6)0.0012 (5)
C40.0215 (8)0.0190 (8)0.0199 (8)0.0036 (6)0.0087 (7)0.0016 (7)
C50.0319 (10)0.0163 (8)0.0257 (9)0.0052 (7)0.0106 (8)0.0036 (7)
C60.0313 (10)0.0138 (8)0.0308 (10)0.0010 (7)0.0131 (8)0.0006 (7)
C70.0226 (8)0.0180 (8)0.0172 (8)0.0013 (6)0.0098 (7)0.0008 (6)
C80.0248 (9)0.0175 (8)0.0152 (8)0.0065 (7)0.0050 (7)0.0004 (6)
C90.0197 (8)0.0201 (8)0.0135 (8)0.0027 (6)0.0009 (6)0.0036 (6)
C100.0225 (9)0.0230 (9)0.0281 (10)0.0061 (7)0.0056 (7)0.0018 (7)
C110.0209 (9)0.0361 (11)0.0420 (12)0.0058 (8)0.0118 (9)0.0014 (9)
C120.0173 (9)0.0344 (10)0.0357 (11)0.0063 (8)0.0056 (8)0.0015 (9)
C130.0273 (10)0.0207 (9)0.0348 (11)0.0020 (7)0.0044 (8)0.0012 (8)
C140.0233 (9)0.0223 (9)0.0243 (9)0.0030 (7)0.0048 (7)0.0044 (7)
C150.0305 (10)0.0163 (8)0.0203 (8)0.0011 (7)0.0098 (7)0.0024 (7)
C160.0310 (10)0.0299 (10)0.0239 (9)0.0013 (8)0.0037 (8)0.0001 (8)
C170.0402 (11)0.0280 (10)0.0172 (9)0.0084 (8)0.0139 (8)0.0006 (7)
C180.0190 (8)0.0228 (9)0.0229 (9)0.0032 (7)0.0107 (7)0.0045 (7)
C190.0189 (9)0.0312 (10)0.0318 (10)0.0006 (7)0.0055 (8)0.0035 (8)
Geometric parameters (Å, º) top
I1—C12.0979 (18)C8—C171.512 (2)
F1—C121.365 (2)C9—C101.390 (2)
O1—C41.397 (2)C9—C141.395 (2)
O1—C151.373 (2)C10—H100.9500
N1—N21.3983 (19)C10—C111.387 (3)
N1—C71.281 (2)C11—H110.9500
C1—C21.386 (2)C11—C121.371 (3)
C1—C61.390 (3)C12—C131.373 (3)
O2—C151.195 (2)C13—H130.9500
N2—C81.491 (2)C13—C141.386 (3)
N2—C181.364 (2)C14—H140.9500
C2—H20.9500C15—C161.493 (3)
C2—C31.400 (2)C16—H16A0.9800
O3—C71.365 (2)C16—H16B0.9800
O3—C81.4515 (19)C16—H16C0.9800
C3—C41.400 (2)C17—H17A0.9800
C3—C71.464 (2)C17—H17B0.9800
O4—C181.222 (2)C17—H17C0.9800
C4—C51.379 (2)C18—C191.500 (3)
C5—H50.9500C19—H19A0.9800
C5—C61.387 (3)C19—H19B0.9800
C6—H60.9500C19—H19C0.9800
C8—C91.523 (2)
C15—O1—C4117.16 (13)C11—C10—H10119.6
C7—N1—N2104.65 (14)C10—C11—H11120.8
C2—C1—I1118.74 (13)C12—C11—C10118.38 (18)
C2—C1—C6120.79 (17)C12—C11—H11120.8
C6—C1—I1120.42 (13)F1—C12—C11119.10 (18)
N1—N2—C8111.07 (13)F1—C12—C13118.09 (18)
C18—N2—N1122.51 (14)C11—C12—C13122.81 (19)
C18—N2—C8126.37 (14)C12—C13—H13120.9
C1—C2—H2120.0C12—C13—C14118.30 (18)
C1—C2—C3120.05 (16)C14—C13—H13120.9
C3—C2—H2120.0C9—C14—H14119.6
C7—O3—C8107.33 (12)C13—C14—C9120.78 (17)
C2—C3—C4118.51 (16)C13—C14—H14119.6
C2—C3—C7118.41 (15)O1—C15—C16110.38 (15)
C4—C3—C7123.02 (16)O2—C15—O1122.66 (17)
O1—C4—C3120.58 (15)O2—C15—C16126.93 (17)
C5—C4—O1118.26 (15)C15—C16—H16A109.5
C5—C4—C3121.07 (16)C15—C16—H16B109.5
C4—C5—H5119.9C15—C16—H16C109.5
C4—C5—C6120.18 (17)H16A—C16—H16B109.5
C6—C5—H5119.9H16A—C16—H16C109.5
C1—C6—H6120.3H16B—C16—H16C109.5
C5—C6—C1119.39 (16)C8—C17—H17A109.5
C5—C6—H6120.3C8—C17—H17B109.5
N1—C7—O3116.20 (15)C8—C17—H17C109.5
N1—C7—C3128.00 (16)H17A—C17—H17B109.5
O3—C7—C3115.78 (15)H17A—C17—H17C109.5
N2—C8—C9111.26 (13)H17B—C17—H17C109.5
N2—C8—C17112.74 (15)N2—C18—C19116.33 (16)
O3—C8—N299.24 (12)O4—C18—N2120.39 (17)
O3—C8—C9109.17 (13)O4—C18—C19123.28 (16)
O3—C8—C17108.06 (14)C18—C19—H19A109.5
C17—C8—C9115.09 (15)C18—C19—H19B109.5
C10—C9—C8120.38 (15)C18—C19—H19C109.5
C10—C9—C14118.86 (17)H19A—C19—H19B109.5
C14—C9—C8120.64 (15)H19A—C19—H19C109.5
C9—C10—H10119.6H19B—C19—H19C109.5
C11—C10—C9120.80 (17)
I1—C1—C2—C3177.52 (12)C6—C1—C2—C30.2 (3)
I1—C1—C6—C5178.17 (13)C7—N1—N2—C87.40 (18)
F1—C12—C13—C14177.44 (17)C7—N1—N2—C18175.13 (15)
O1—C4—C5—C6176.19 (16)C7—O3—C8—N211.41 (16)
N1—N2—C8—O311.66 (16)C7—O3—C8—C9105.04 (15)
N1—N2—C8—C9103.18 (15)C7—O3—C8—C17129.12 (15)
N1—N2—C8—C17125.79 (15)C7—C3—C4—O17.2 (2)
N1—N2—C18—O4177.18 (15)C7—C3—C4—C5176.30 (16)
N1—N2—C18—C192.7 (2)C8—N2—C18—O40.1 (3)
C1—C2—C3—C40.8 (2)C8—N2—C18—C19179.75 (15)
C1—C2—C3—C7176.69 (15)C8—O3—C7—N18.6 (2)
N2—N1—C7—O30.70 (19)C8—O3—C7—C3169.74 (14)
N2—N1—C7—C3177.36 (16)C8—C9—C10—C11173.47 (17)
N2—C8—C9—C1090.33 (18)C8—C9—C14—C13173.28 (16)
N2—C8—C9—C1485.57 (19)C9—C10—C11—C120.2 (3)
C2—C1—C6—C50.9 (3)C10—C9—C14—C132.7 (3)
C2—C3—C4—O1175.43 (14)C10—C11—C12—F1177.25 (18)
C2—C3—C4—C51.0 (2)C10—C11—C12—C132.1 (3)
C2—C3—C7—N1178.95 (17)C11—C12—C13—C141.9 (3)
C2—C3—C7—O30.9 (2)C12—C13—C14—C90.6 (3)
O3—C8—C9—C1018.2 (2)C14—C9—C10—C112.5 (3)
O3—C8—C9—C14165.92 (15)C15—O1—C4—C381.4 (2)
C3—C4—C5—C60.3 (3)C15—O1—C4—C5102.02 (18)
C4—O1—C15—O25.6 (2)C17—C8—C9—C10139.87 (17)
C4—O1—C15—C16176.14 (14)C17—C8—C9—C1444.2 (2)
C4—C3—C7—N11.6 (3)C18—N2—C8—O3170.99 (15)
C4—C3—C7—O3176.45 (15)C18—N2—C8—C974.2 (2)
C4—C5—C6—C10.6 (3)C18—N2—C8—C1756.9 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.533.331 (2)142
C14—H14···O2ii0.952.513.335 (2)145
C16—H16A···O4iii0.982.543.513 (2)174
C17—H17C···Cg3ii0.982.503.407 (2)154
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+3/2, z+1/2; (iii) x, y+3/2, z1/2.
2-[4-Acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6e) top
Crystal data top
C19H16ClIN2O4F(000) = 984
Mr = 498.69Dx = 1.736 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.703 (2) ÅCell parameters from 9499 reflections
b = 22.037 (4) Åθ = 2.9–31.1°
c = 7.4073 (12) ŵ = 1.85 mm1
β = 92.888 (8)°T = 100 K
V = 1907.9 (5) Å3Block, colourless
Z = 40.22 × 0.12 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
3863 reflections with I > 2σ(I)
φ and ω scansRint = 0.042
Absorption correction: multi-scan
SADABS2014/2 (Bruker, 2014)
θmax = 27.5°, θmin = 2.9°
Tmin = 0.640, Tmax = 0.746h = 1515
62840 measured reflectionsk = 2828
4387 independent reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0233P)2 + 1.3951P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
4387 reflectionsΔρmax = 0.40 e Å3
247 parametersΔρmin = 0.66 e Å3
0 restraints
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
I10.89006 (2)0.30547 (2)0.88485 (2)0.03207 (5)
Cl10.06374 (4)0.34278 (2)0.41999 (8)0.03241 (12)
O10.77394 (10)0.50823 (5)0.31612 (16)0.0169 (2)
N10.64395 (12)0.42152 (6)0.12176 (18)0.0155 (3)
C10.84397 (15)0.37358 (8)0.6975 (2)0.0175 (3)
O20.91227 (11)0.47025 (6)0.14881 (17)0.0219 (3)
N20.56147 (13)0.38760 (6)0.02279 (19)0.0165 (3)
C20.77370 (14)0.35965 (7)0.5465 (2)0.0156 (3)
H20.7425010.3200350.5324210.019*
O30.61627 (10)0.33434 (5)0.27089 (16)0.0156 (2)
C30.74881 (14)0.40416 (7)0.4147 (2)0.0135 (3)
O40.44240 (12)0.37370 (6)0.22008 (18)0.0279 (3)
C40.79720 (14)0.46180 (7)0.4405 (2)0.0147 (3)
C50.86500 (15)0.47563 (8)0.5935 (2)0.0176 (3)
H50.8955680.5153240.6092080.021*
C60.88836 (15)0.43149 (8)0.7241 (2)0.0183 (3)
H60.9340580.4408050.8301140.022*
C70.67047 (14)0.38903 (7)0.2610 (2)0.0137 (3)
C80.53275 (14)0.33051 (7)0.1187 (2)0.0145 (3)
C90.41367 (14)0.33227 (7)0.1917 (2)0.0142 (3)
C100.39456 (15)0.36749 (8)0.3436 (2)0.0193 (4)
H100.4560420.3899650.3992030.023*
C110.28763 (16)0.37029 (8)0.4149 (2)0.0209 (4)
H110.2754420.3942480.5187960.025*
C120.19911 (15)0.33766 (8)0.3323 (2)0.0191 (4)
C130.21483 (16)0.30168 (8)0.1829 (3)0.0226 (4)
H130.1529880.2790550.1290090.027*
C140.32285 (16)0.29914 (8)0.1126 (2)0.0198 (4)
H140.3347640.2745920.0097820.024*
C150.84064 (15)0.50789 (8)0.1683 (2)0.0172 (3)
C160.81145 (19)0.56051 (9)0.0475 (3)0.0292 (4)
H16A0.8019650.5969840.1209470.044*
H16B0.7400150.5520370.0226980.044*
H16C0.8732080.5670200.0349170.044*
C170.55813 (15)0.27428 (8)0.0106 (2)0.0197 (4)
H17A0.5482980.2381870.0855340.029*
H17B0.6370730.2760050.0273850.029*
H17C0.5054530.2722320.0963340.029*
C180.51525 (15)0.40515 (8)0.1420 (2)0.0190 (4)
C190.55873 (17)0.46367 (9)0.2175 (2)0.0239 (4)
H19A0.5161260.4730140.3314410.036*
H19B0.6402460.4595790.2395690.036*
H19C0.5481470.4965320.1308300.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02554 (8)0.03502 (8)0.03427 (8)0.00758 (5)0.01207 (5)0.02000 (6)
Cl10.0206 (2)0.0319 (3)0.0460 (3)0.00113 (19)0.0134 (2)0.0002 (2)
O10.0224 (6)0.0132 (5)0.0153 (6)0.0002 (5)0.0019 (5)0.0013 (4)
N10.0162 (7)0.0158 (7)0.0143 (7)0.0012 (5)0.0003 (5)0.0009 (5)
C10.0145 (8)0.0224 (9)0.0156 (8)0.0002 (7)0.0005 (6)0.0049 (7)
O20.0227 (7)0.0242 (7)0.0192 (6)0.0005 (5)0.0047 (5)0.0013 (5)
N20.0183 (7)0.0169 (7)0.0140 (7)0.0030 (6)0.0019 (6)0.0012 (5)
C20.0144 (8)0.0151 (8)0.0174 (8)0.0022 (6)0.0011 (6)0.0005 (6)
O30.0157 (6)0.0147 (6)0.0158 (6)0.0030 (5)0.0048 (5)0.0014 (4)
C30.0114 (8)0.0156 (8)0.0135 (7)0.0004 (6)0.0018 (6)0.0005 (6)
O40.0291 (8)0.0343 (8)0.0191 (7)0.0041 (6)0.0088 (6)0.0005 (6)
C40.0152 (8)0.0155 (8)0.0137 (8)0.0010 (6)0.0034 (6)0.0007 (6)
C50.0190 (9)0.0168 (8)0.0173 (8)0.0037 (7)0.0030 (7)0.0032 (6)
C60.0149 (8)0.0259 (9)0.0141 (8)0.0037 (7)0.0001 (6)0.0018 (7)
C70.0130 (8)0.0131 (7)0.0152 (8)0.0004 (6)0.0026 (6)0.0010 (6)
C80.0150 (8)0.0156 (8)0.0125 (8)0.0013 (6)0.0023 (6)0.0004 (6)
C90.0165 (8)0.0127 (7)0.0131 (8)0.0012 (6)0.0018 (6)0.0009 (6)
C100.0196 (9)0.0206 (8)0.0174 (8)0.0013 (7)0.0018 (7)0.0049 (7)
C110.0243 (9)0.0205 (9)0.0179 (9)0.0040 (7)0.0023 (7)0.0044 (7)
C120.0158 (8)0.0188 (8)0.0231 (9)0.0027 (7)0.0047 (7)0.0055 (7)
C130.0176 (9)0.0226 (9)0.0273 (10)0.0036 (7)0.0012 (7)0.0031 (7)
C140.0197 (9)0.0207 (9)0.0189 (8)0.0012 (7)0.0008 (7)0.0062 (7)
C150.0180 (8)0.0179 (8)0.0155 (8)0.0062 (7)0.0002 (7)0.0010 (6)
C160.0346 (11)0.0273 (10)0.0258 (10)0.0006 (8)0.0021 (8)0.0121 (8)
C170.0191 (9)0.0193 (8)0.0208 (9)0.0004 (7)0.0023 (7)0.0054 (7)
C180.0196 (9)0.0228 (9)0.0146 (8)0.0048 (7)0.0011 (7)0.0002 (7)
C190.0308 (10)0.0254 (9)0.0156 (9)0.0029 (8)0.0022 (7)0.0053 (7)
Geometric parameters (Å, º) top
I1—C12.0963 (17)C8—C171.513 (2)
Cl1—C121.7459 (18)C9—C101.395 (2)
O1—C41.395 (2)C9—C141.394 (2)
O1—C151.377 (2)C10—H100.9500
N1—N21.399 (2)C10—C111.384 (3)
N1—C71.281 (2)C11—H110.9500
C1—C21.389 (2)C11—C121.379 (3)
C1—C61.388 (2)C12—C131.381 (3)
O2—C151.193 (2)C13—H130.9500
N2—C81.491 (2)C13—C141.392 (3)
N2—C181.366 (2)C14—H140.9500
C2—H20.9500C15—C161.493 (2)
C2—C31.404 (2)C16—H16A0.9800
O3—C71.366 (2)C16—H16B0.9800
O3—C81.4568 (19)C16—H16C0.9800
C3—C41.400 (2)C17—H17A0.9800
C3—C71.464 (2)C17—H17B0.9800
O4—C181.221 (2)C17—H17C0.9800
C4—C51.384 (2)C18—C191.505 (3)
C5—H50.9500C19—H19A0.9800
C5—C61.389 (2)C19—H19B0.9800
C6—H60.9500C19—H19C0.9800
C8—C91.520 (2)
C15—O1—C4114.96 (13)C11—C10—H10119.4
C7—N1—N2104.84 (14)C10—C11—H11120.6
C2—C1—I1119.80 (13)C12—C11—C10118.76 (16)
C6—C1—I1118.83 (13)C12—C11—H11120.6
C6—C1—C2121.32 (16)C11—C12—Cl1118.47 (14)
N1—N2—C8111.55 (13)C11—C12—C13121.84 (16)
C18—N2—N1123.28 (14)C13—C12—Cl1119.69 (14)
C18—N2—C8125.17 (14)C12—C13—H13120.6
C1—C2—H2120.0C12—C13—C14118.87 (17)
C1—C2—C3119.95 (15)C14—C13—H13120.6
C3—C2—H2120.0C9—C14—H14119.7
C7—O3—C8107.76 (12)C13—C14—C9120.60 (16)
C2—C3—C7118.79 (15)C13—C14—H14119.7
C4—C3—C2118.07 (15)O1—C15—C16110.52 (15)
C4—C3—C7123.10 (15)O2—C15—O1122.00 (15)
O1—C4—C3120.76 (15)O2—C15—C16127.46 (17)
C5—C4—O1117.65 (15)C15—C16—H16A109.5
C5—C4—C3121.53 (15)C15—C16—H16B109.5
C4—C5—H5120.0C15—C16—H16C109.5
C4—C5—C6120.03 (16)H16A—C16—H16B109.5
C6—C5—H5120.0H16A—C16—H16C109.5
C1—C6—C5119.06 (16)H16B—C16—H16C109.5
C1—C6—H6120.5C8—C17—H17A109.5
C5—C6—H6120.5C8—C17—H17B109.5
N1—C7—O3116.24 (15)C8—C17—H17C109.5
N1—C7—C3128.02 (15)H17A—C17—H17B109.5
O3—C7—C3115.71 (14)H17A—C17—H17C109.5
N2—C8—C9112.35 (14)H17B—C17—H17C109.5
N2—C8—C17112.57 (14)N2—C18—C19116.68 (16)
O3—C8—N299.28 (12)O4—C18—N2119.87 (16)
O3—C8—C9108.34 (13)O4—C18—C19123.46 (16)
O3—C8—C17108.37 (13)C18—C19—H19A109.5
C17—C8—C9114.64 (14)C18—C19—H19B109.5
C10—C9—C8119.22 (15)C18—C19—H19C109.5
C14—C9—C8122.03 (15)H19A—C19—H19B109.5
C14—C9—C10118.74 (16)H19A—C19—H19C109.5
C9—C10—H10119.4H19B—C19—H19C109.5
C11—C10—C9121.16 (16)
I1—C1—C2—C3175.79 (12)C6—C1—C2—C31.7 (3)
I1—C1—C6—C5175.24 (13)C7—N1—N2—C82.98 (18)
Cl1—C12—C13—C14178.69 (14)C7—N1—N2—C18176.27 (16)
O1—C4—C5—C6178.30 (15)C7—O3—C8—N25.51 (15)
N1—N2—C8—O35.26 (16)C7—O3—C8—C9111.89 (14)
N1—N2—C8—C9109.07 (15)C7—O3—C8—C17123.16 (14)
N1—N2—C8—C17119.69 (15)C7—C3—C4—O11.2 (2)
N1—N2—C18—O4179.05 (16)C7—C3—C4—C5175.70 (15)
N1—N2—C18—C190.9 (2)C8—N2—C18—O41.8 (3)
C1—C2—C3—C40.4 (2)C8—N2—C18—C19178.20 (15)
C1—C2—C3—C7177.32 (15)C8—O3—C7—N14.56 (19)
N2—N1—C7—O30.98 (19)C8—O3—C7—C3173.32 (13)
N2—N1—C7—C3176.59 (16)C8—C9—C10—C11179.82 (16)
N2—C8—C9—C1074.07 (19)C8—C9—C14—C13179.91 (16)
N2—C8—C9—C14106.70 (18)C9—C10—C11—C120.3 (3)
C2—C1—C6—C52.3 (3)C10—C9—C14—C130.7 (3)
C2—C3—C4—O1178.77 (14)C10—C11—C12—Cl1178.58 (14)
C2—C3—C4—C51.9 (2)C10—C11—C12—C131.1 (3)
C2—C3—C7—N1174.43 (16)C11—C12—C13—C141.0 (3)
C2—C3—C7—O38.0 (2)C12—C13—C14—C90.1 (3)
O3—C8—C9—C1034.6 (2)C14—C9—C10—C110.6 (3)
O3—C8—C9—C14144.63 (15)C15—O1—C4—C383.54 (19)
C3—C4—C5—C61.3 (3)C15—O1—C4—C599.47 (17)
C4—O1—C15—O20.4 (2)C17—C8—C9—C10155.75 (16)
C4—O1—C15—C16178.08 (15)C17—C8—C9—C1423.5 (2)
C4—C3—C7—N18.0 (3)C18—N2—C8—O3173.97 (15)
C4—C3—C7—O3169.58 (15)C18—N2—C8—C971.7 (2)
C4—C5—C6—C10.8 (3)C18—N2—C8—C1759.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.473.258 (2)140
C11—H11···O1ii0.952.553.435 (2)155
C19—H19B···Cg2iii0.982.753.649 (2)153
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y, z1.
Cytotoxic effects of the examined compounds 6a6i (IC50a) in µM) top
CompoundKBHep-G2
6a3.733±0.47212.574±0.766
6b9.214±0.88414.735±0.727
6c5.280±0.81912.284±0.625
6d1.867±0.5684.564±0.539
6e4.012±0.6223.811±0.822
6f0.921±0.3603.315±0.552
6g6.262±0.64513.260±0.866
6h3.166±0.3983.983±0.482
6i12.476±0.97911.900±1.036
Elipcitine1.260±0,5282.358±0.407
Note: (a) IC50 is the concentration of the compound required to inhibit cell growth by 50%.
 

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