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Phthalonitrile derivatives are generally reported to crystallize in space groups P21/c and P1 in the literature. In this study, 7-hydroxy-4,8-dimethyl-3-pentylcoumarin (2) and its phthalonitrile derivative (2d) were crystallized; 2d crystallized in the rare trigonal space group R3. In the phthalonitrile derivative (2d), weak C—H...O hydrogen-bonding interactions promoted the formation of supramolecular double helices, and these supramolecular P and M double helices came together to form a honeycomb-like architectural motif involving one-dimensional tubular channels. In silico molecular-docking studies were performed to support the experimental processes and the results agree with each other. In vitro studies of compounds 2 and 2d were performed in LoVo colorectal adenocarcinoma and CCD18Co healthy human cell lines using flow cytometry. For compounds 2 and 2d, there was a statistically significant increase (p < 0.001) in both early and late apoptosis with respect to the control in a dose-dependent manner.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2059798322007823/di5058sup1.cif
Contains datablocks 21gtu143_fs_2_0ma, 21gtu181_fs_1_0m

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2059798322007823/di5058sup2.pdf
Supplementary Figures and Tables.

CCDC references: 2158229; 2158230

Computing details top

For both structures, program(s) used to solve structure: SHELXT 2014/4 (Sheldrick, 2014); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

(21gtu143_fs_2_0ma) top
Crystal data top
C24H22N2O3·[+solvents]Dx = 1.090 Mg m3
Mr = 386.43Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 1475 reflections
a = 49.850 (7) Åθ = 2.2–18.7°
c = 4.9234 (8) ŵ = 0.07 mm1
V = 10596 (3) Å3T = 296 K
Z = 18Plate, colourless
F(000) = 36720.26 × 0.10 × 0.09 mm
Data collection top
Bruker APEX-II CCD
diffractometer
4177 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs1911 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.061
Detector resolution: 7.9 pixels mm-1θmax = 25.1°, θmin = 0.8°
φ and ω scansh = 3759
Absorption correction: multi-scan
SADABS V2014/4 (Bruker AXS)
k = 5848
Tmin = 0.393, Tmax = 0.746l = 55
13237 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.110H-atom parameters constrained
wR(F2) = 0.378 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
4177 reflectionsΔρmax = 0.42 e Å3
294 parametersΔρmin = 0.29 e Å3
290 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*/UeqOcc. (<1)
O10.58536 (9)0.66105 (8)0.3036 (7)0.0821 (12)
O20.58900 (11)0.69363 (9)0.0062 (8)0.1089 (14)
O30.58604 (9)0.59571 (8)0.9902 (7)0.0808 (12)
N10.50369 (11)0.46859 (10)0.6091 (10)0.0844 (13)
N20.55298 (11)0.44869 (13)1.1255 (12)0.0977 (14)
C20.57141 (19)0.67297 (14)0.1453 (13)0.0964 (15)
C30.53856 (17)0.66050 (12)0.1646 (11)0.0818 (16)
C40.52125 (15)0.63695 (13)0.3410 (12)0.0816 (14)
C50.52189 (13)0.60265 (12)0.7127 (11)0.0689 (14)
H50.5006560.5940280.7373630.083*
C60.53775 (13)0.59287 (11)0.8681 (10)0.0668 (14)
H60.5275970.5780091.0020520.080*
C70.56909 (13)0.60513 (11)0.8261 (10)0.0657 (14)
C80.58553 (13)0.62776 (12)0.6380 (11)0.0753 (14)
C90.56861 (13)0.63788 (11)0.4897 (10)0.0644 (14)
C100.53712 (13)0.62563 (11)0.5148 (10)0.0647 (13)
C110.48694 (14)0.62201 (13)0.3592 (12)0.0887 (15)
H11A0.4777760.6002220.3244200.133*
H11B0.4796750.6310690.2271250.133*
H11C0.4812380.6251000.5378120.133*
C120.61999 (13)0.64097 (13)0.5966 (12)0.0854 (15)
H12A0.6250590.6463820.4089840.128*
H12B0.6255340.6257760.6473760.128*
H12C0.6312190.6591120.7071840.128*
C130.52451 (18)0.67409 (14)0.0226 (12)0.1049 (18)
H13A0.5040350.6578850.0767260.126*
H13B0.5371130.6817200.1851930.126*
C140.5219 (2)0.70050 (17)0.1077 (14)0.126 (2)
H14A0.5422880.7185650.1312770.152*0.558 (8)
H14B0.5119710.6942800.2838830.152*0.558 (8)
H14C0.5075460.6913470.2577890.152*0.442 (8)
H14D0.5420030.7141940.1879780.152*0.442 (8)
C15A0.5023 (4)0.7077 (4)0.088 (3)0.150 (3)0.558 (8)
H15A0.5135500.7158910.2563250.180*0.558 (8)
H15B0.4832370.6887390.1294350.180*0.558 (8)
C15B0.5127 (5)0.7208 (4)0.035 (5)0.146 (3)0.442 (8)
H15C0.5243530.7287950.2024670.175*0.442 (8)
H15D0.5159200.7380060.0787020.175*0.442 (8)
C16A0.4944 (4)0.7311 (4)0.032 (3)0.160 (3)0.558 (8)
H16A0.5133120.7494280.0891040.192*0.558 (8)
H16B0.4813870.7222010.1908480.192*0.558 (8)
C16B0.4788 (5)0.6995 (5)0.092 (5)0.161 (3)0.442 (8)
H16C0.4773510.6874810.2523800.193*0.442 (8)
H16D0.4704050.6850050.0581220.193*0.442 (8)
C17A0.4775 (4)0.7401 (4)0.178 (4)0.162 (3)0.558 (8)
H17A0.4685360.7243990.3150500.243*0.558 (8)
H17B0.4919410.7595200.2598840.243*0.558 (8)
H17C0.4614110.7420950.0888780.243*0.558 (8)
C17B0.4579 (5)0.7127 (5)0.136 (5)0.162 (3)0.442 (8)
H17D0.4602430.7202620.3186210.243*0.442 (8)
H17E0.4633130.7293850.0107930.243*0.442 (8)
H17F0.4367970.6968260.1063610.243*0.442 (8)
C180.57731 (12)0.56516 (12)1.0092 (10)0.0642 (13)
C190.55447 (11)0.54189 (11)0.8484 (9)0.0591 (13)
H190.5439360.5466580.7186510.071*
C200.54772 (11)0.51164 (11)0.8850 (9)0.0576 (12)
C210.56434 (11)0.50469 (12)1.0723 (10)0.0641 (13)
C220.58679 (12)0.52859 (13)1.2290 (11)0.0716 (15)
H220.5975530.5240911.3584430.086*
C230.59334 (12)0.55812 (13)1.1979 (10)0.0714 (15)
H230.6086510.5737431.3034670.086*
C240.52381 (14)0.48802 (12)0.7306 (11)0.0739 (13)
C250.55801 (13)0.47377 (15)1.1043 (14)0.0881 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.096 (3)0.054 (2)0.066 (2)0.0140 (19)0.0202 (19)0.0061 (18)
O20.142 (3)0.067 (2)0.086 (3)0.029 (2)0.019 (2)0.0139 (18)
O30.086 (2)0.053 (2)0.083 (2)0.0191 (19)0.020 (2)0.0085 (18)
N10.086 (3)0.058 (2)0.087 (3)0.020 (2)0.017 (2)0.008 (2)
N20.072 (2)0.084 (3)0.126 (3)0.031 (3)0.011 (2)0.022 (3)
C20.135 (3)0.058 (2)0.078 (3)0.035 (2)0.019 (2)0.009 (2)
C30.128 (4)0.056 (3)0.059 (3)0.043 (3)0.009 (3)0.012 (2)
C40.099 (3)0.060 (3)0.079 (3)0.035 (2)0.009 (3)0.018 (2)
C50.072 (3)0.051 (3)0.072 (3)0.022 (2)0.012 (3)0.009 (2)
C60.078 (3)0.041 (3)0.069 (3)0.021 (2)0.007 (3)0.003 (2)
C70.074 (3)0.040 (2)0.066 (3)0.017 (2)0.005 (3)0.012 (2)
C80.073 (2)0.054 (2)0.074 (3)0.012 (2)0.005 (2)0.009 (2)
C90.077 (3)0.041 (2)0.053 (3)0.013 (2)0.012 (2)0.001 (2)
C100.079 (3)0.044 (2)0.056 (3)0.020 (2)0.005 (2)0.007 (2)
C110.102 (3)0.067 (3)0.086 (3)0.034 (2)0.012 (3)0.015 (2)
C120.078 (3)0.062 (2)0.082 (3)0.010 (2)0.005 (2)0.007 (2)
C130.156 (5)0.078 (3)0.080 (4)0.057 (3)0.015 (3)0.009 (3)
C140.181 (5)0.100 (4)0.118 (4)0.086 (4)0.016 (4)0.014 (3)
C15A0.193 (6)0.120 (5)0.156 (5)0.093 (5)0.026 (5)0.001 (5)
C15B0.195 (6)0.116 (5)0.154 (5)0.099 (4)0.020 (5)0.004 (5)
C16A0.197 (6)0.131 (5)0.178 (5)0.102 (4)0.027 (5)0.001 (5)
C16B0.197 (6)0.132 (5)0.177 (5)0.100 (5)0.027 (5)0.000 (5)
C17A0.198 (6)0.132 (5)0.180 (5)0.100 (4)0.027 (5)0.000 (5)
C17B0.198 (6)0.132 (5)0.179 (5)0.100 (4)0.027 (5)0.000 (5)
C180.064 (3)0.056 (3)0.054 (3)0.016 (2)0.000 (2)0.005 (2)
C190.061 (3)0.054 (3)0.051 (3)0.020 (2)0.001 (2)0.007 (2)
C200.056 (3)0.052 (2)0.054 (3)0.020 (2)0.003 (2)0.004 (2)
C210.051 (3)0.060 (3)0.066 (3)0.017 (2)0.012 (2)0.008 (2)
C220.054 (3)0.072 (3)0.072 (3)0.020 (3)0.004 (2)0.009 (3)
C230.061 (3)0.067 (3)0.062 (3)0.014 (3)0.009 (2)0.003 (3)
C240.078 (3)0.052 (2)0.080 (3)0.023 (2)0.015 (2)0.007 (2)
C250.067 (2)0.078 (3)0.118 (3)0.035 (3)0.012 (2)0.024 (3)
Geometric parameters (Å, º) top
O1—C21.363 (8)C14—H14D0.9700
O1—C91.381 (6)C14—C15A1.540 (8)
O2—C21.218 (7)C14—C15B1.480 (15)
O3—C71.409 (6)C15A—H15A0.9700
O3—C181.362 (6)C15A—H15B0.9700
N1—C241.154 (6)C15A—C16A1.520 (9)
N2—C251.151 (7)C15B—H15C0.9700
C2—C31.435 (9)C15B—H15D0.9700
C3—C41.365 (8)C15B—C16B1.507 (17)
C3—C131.508 (8)C16A—H16A0.9700
C4—C101.457 (8)C16A—H16B0.9700
C4—C111.488 (8)C16A—C17A1.537 (9)
C5—H50.9300C16B—H16C0.9700
C5—C61.354 (7)C16B—H16D0.9700
C5—C101.403 (7)C16B—C17B1.501 (17)
C6—H60.9300C17A—H17A0.9600
C6—C71.379 (7)C17A—H17B0.9600
C7—C81.370 (7)C17A—H17C0.9600
C8—C91.387 (8)C17B—H17D0.9600
C8—C121.515 (8)C17B—H17E0.9600
C9—C101.376 (8)C17B—H17F0.9600
C11—H11A0.9600C18—C191.396 (6)
C11—H11B0.9600C18—C231.381 (7)
C11—H11C0.9600C19—H190.9300
C12—H12A0.9600C19—C201.383 (7)
C12—H12B0.9600C20—C211.394 (7)
C12—H12C0.9600C20—C241.408 (7)
C13—H13A0.9700C21—C221.391 (7)
C13—H13B0.9700C21—C251.419 (8)
C13—C141.527 (7)C22—H220.9300
C14—H14A0.9700C22—C231.348 (7)
C14—H14B0.9700C23—H230.9300
C14—H14C0.9700
C2—O1—C9121.2 (5)C15B—C14—H14D106.0
C18—O3—C7120.2 (4)C14—C15A—H15A109.2
O1—C2—C3119.6 (6)C14—C15A—H15B109.2
O2—C2—O1114.2 (7)H15A—C15A—H15B107.9
O2—C2—C3126.2 (7)C16A—C15A—C14112.0 (8)
C2—C3—C13116.8 (6)C16A—C15A—H15A109.2
C4—C3—C2120.6 (6)C16A—C15A—H15B109.2
C4—C3—C13122.6 (7)C14—C15B—H15C111.1
C3—C4—C10118.3 (6)C14—C15B—H15D111.1
C3—C4—C11122.9 (6)C14—C15B—C16B103.2 (13)
C10—C4—C11118.8 (5)H15C—C15B—H15D109.1
C6—C5—H5119.6C16B—C15B—H15C111.1
C6—C5—C10120.7 (5)C16B—C15B—H15D111.1
C10—C5—H5119.6C15A—C16A—H16A109.5
C5—C6—H6120.3C15A—C16A—H16B109.5
C5—C6—C7119.4 (5)C15A—C16A—C17A110.6 (8)
C7—C6—H6120.3H16A—C16A—H16B108.1
C6—C7—O3120.1 (5)C17A—C16A—H16A109.5
C8—C7—O3116.8 (5)C17A—C16A—H16B109.5
C8—C7—C6123.0 (5)C15B—C16B—H16C107.4
C7—C8—C9115.7 (5)C15B—C16B—H16D107.4
C7—C8—C12122.0 (6)H16C—C16B—H16D106.9
C9—C8—C12122.3 (5)C17B—C16B—C15B119.9 (17)
O1—C9—C8115.5 (5)C17B—C16B—H16C107.4
C10—C9—O1120.6 (5)C17B—C16B—H16D107.4
C10—C9—C8123.9 (5)C16A—C17A—H17A109.5
C5—C10—C4123.2 (5)C16A—C17A—H17B109.5
C9—C10—C4119.7 (5)C16A—C17A—H17C109.5
C9—C10—C5117.2 (5)H17A—C17A—H17B109.5
C4—C11—H11A109.5H17A—C17A—H17C109.5
C4—C11—H11B109.5H17B—C17A—H17C109.5
C4—C11—H11C109.5C16B—C17B—H17D109.5
H11A—C11—H11B109.5C16B—C17B—H17E109.5
H11A—C11—H11C109.5C16B—C17B—H17F109.5
H11B—C11—H11C109.5H17D—C17B—H17E109.5
C8—C12—H12A109.5H17D—C17B—H17F109.5
C8—C12—H12B109.5H17E—C17B—H17F109.5
C8—C12—H12C109.5O3—C18—C19124.2 (5)
H12A—C12—H12B109.5O3—C18—C23115.4 (5)
H12A—C12—H12C109.5C23—C18—C19120.4 (5)
H12B—C12—H12C109.5C18—C19—H19120.5
C3—C13—H13A109.0C20—C19—C18119.0 (5)
C3—C13—H13B109.0C20—C19—H19120.5
C3—C13—C14112.9 (5)C19—C20—C21120.4 (5)
H13A—C13—H13B107.8C19—C20—C24119.0 (5)
C14—C13—H13A109.0C21—C20—C24120.6 (5)
C14—C13—H13B109.0C20—C21—C25120.4 (5)
C13—C14—H14A110.5C22—C21—C20118.5 (5)
C13—C14—H14B110.5C22—C21—C25121.1 (5)
C13—C14—H14C106.0C21—C22—H22119.2
C13—C14—H14D106.0C23—C22—C21121.6 (5)
C13—C14—C15A106.1 (6)C23—C22—H22119.2
H14A—C14—H14B108.7C18—C23—H23120.0
H14C—C14—H14D106.3C22—C23—C18120.0 (5)
C15A—C14—H14A110.5C22—C23—H23120.0
C15A—C14—H14B110.5N1—C24—C20178.3 (6)
C15B—C14—C13125.3 (11)N2—C25—C21178.8 (8)
C15B—C14—H14C106.0
O1—C2—C3—C40.3 (8)C7—C8—C9—C102.9 (7)
O1—C2—C3—C13178.1 (5)C8—C9—C10—C4177.3 (5)
O1—C9—C10—C40.7 (7)C8—C9—C10—C53.3 (7)
O1—C9—C10—C5178.6 (4)C9—O1—C2—O2178.7 (4)
O2—C2—C3—C4179.1 (6)C9—O1—C2—C32.3 (8)
O2—C2—C3—C130.7 (9)C10—C5—C6—C71.7 (7)
O3—C7—C8—C9176.4 (4)C11—C4—C10—C54.5 (7)
O3—C7—C8—C123.2 (7)C11—C4—C10—C9176.2 (5)
O3—C18—C19—C20179.6 (5)C12—C8—C9—O10.6 (7)
O3—C18—C23—C22178.9 (5)C12—C8—C9—C10177.5 (5)
C2—O1—C9—C8180.0 (5)C13—C3—C4—C10179.5 (5)
C2—O1—C9—C101.8 (7)C13—C3—C4—C111.7 (8)
C2—C3—C4—C102.1 (8)C13—C14—C15A—C16A173.0 (14)
C2—C3—C4—C11176.7 (5)C13—C14—C15B—C16B70 (2)
C2—C3—C13—C1493.4 (8)C14—C15A—C16A—C17A174.6 (15)
C3—C4—C10—C5176.7 (4)C14—C15B—C16B—C17B157 (2)
C3—C4—C10—C92.6 (7)C18—O3—C7—C656.2 (6)
C3—C13—C14—C15A170.4 (10)C18—O3—C7—C8127.1 (5)
C3—C13—C14—C15B172.1 (12)C18—C19—C20—C212.5 (7)
C4—C3—C13—C1488.1 (7)C18—C19—C20—C24177.4 (5)
C5—C6—C7—O3178.6 (4)C19—C18—C23—C220.5 (8)
C5—C6—C7—C82.1 (7)C19—C20—C21—C222.8 (7)
C6—C5—C10—C4179.7 (4)C19—C20—C21—C25178.2 (5)
C6—C5—C10—C90.9 (7)C20—C21—C22—C232.0 (8)
C6—C7—C8—C90.1 (7)C21—C22—C23—C180.8 (8)
C6—C7—C8—C12179.7 (5)C23—C18—C19—C201.3 (7)
C7—O3—C18—C198.5 (7)C24—C20—C21—C22177.1 (5)
C7—O3—C18—C23173.1 (4)C24—C20—C21—C251.9 (7)
C7—C8—C9—O1179.0 (4)C25—C21—C22—C23179.0 (5)
(21gtu181_fs_1_0m) top
Crystal data top
C16H20O3Dx = 1.220 Mg m3
Mr = 260.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 1711 reflections
a = 29.189 (8) Åθ = 2.7–22.6°
b = 5.5877 (15) ŵ = 0.08 mm1
c = 8.686 (3) ÅT = 298 K
V = 1416.7 (7) Å3Block, colourless
Z = 40.19 × 0.14 × 0.10 mm
F(000) = 560
Data collection top
Bruker APEX-II CCD
diffractometer
2415 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs1700 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.057
Detector resolution: 7.9 pixels mm-1θmax = 25.0°, θmin = 1.4°
ω and φ scansh = 3432
Absorption correction: multi-scan
SADABS V2014/4 (Bruker AXS)
k = 66
Tmin = 0.393, Tmax = 0.746l = 1010
6701 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.074 w = 1/[σ2(Fo2) + (0.1144P)2 + 0.4608P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.211(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.28 e Å3
2415 reflectionsΔρmin = 0.25 e Å3
186 parametersAbsolute structure: Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
42 restraintsAbsolute structure parameter: 0.6 (10)
Primary atom site location: dual
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)
O10.69987 (15)0.1949 (7)0.3862 (4)0.0461 (11)
O20.64576 (17)0.0130 (8)0.5000 (6)0.0689 (15)
O30.82287 (16)0.6022 (8)0.1601 (6)0.0637 (14)
H30.8280150.7134630.1009820.096*
C20.6542 (2)0.1560 (11)0.4157 (7)0.0526 (17)
C30.6204 (2)0.3094 (11)0.3446 (8)0.0517 (16)
C40.6350 (2)0.4920 (11)0.2514 (7)0.0509 (17)
C50.7006 (2)0.7136 (11)0.1311 (8)0.0535 (18)
H50.6807860.8217280.0844290.064*
C60.7464 (2)0.7370 (10)0.1080 (8)0.0547 (17)
H60.7574420.8575000.0440500.066*
C70.7773 (2)0.5797 (10)0.1803 (7)0.0466 (15)
C80.7614 (2)0.3959 (10)0.2731 (7)0.0434 (15)
C90.7145 (2)0.3781 (10)0.2927 (6)0.0419 (14)
C100.6823 (2)0.5299 (10)0.2239 (7)0.0415 (14)
C110.6006 (2)0.6525 (14)0.1714 (10)0.071 (2)
H11A0.6029790.8118380.2119160.106*
H11B0.5702480.5923570.1886640.106*
H11C0.6068520.6549170.0628730.106*
C120.7942 (3)0.2276 (12)0.3499 (9)0.0577 (18)
H12A0.8143410.1599730.2741770.087*
H12B0.7773670.1018650.3996300.087*
H12C0.8118560.3132550.4251100.087*
C130.5713 (3)0.2591 (13)0.3834 (10)0.080 (2)
H13A0.5691410.0946540.4184240.096*
H13B0.5534520.2719400.2896590.096*
C140.5497 (4)0.4167 (18)0.5030 (10)0.105 (3)
H14A0.5570890.5818370.4791000.126*0.796 (18)
H14B0.5166840.3997950.4958270.126*0.796 (18)
H14C0.5292920.5186150.4440430.126*0.204 (18)
H14D0.5745520.5200570.5357510.126*0.204 (18)
C15A0.5637 (5)0.3677 (18)0.6644 (13)0.102 (4)0.796 (18)
H15A0.5547500.5009980.7293720.122*0.796 (18)
H15B0.5967590.3522410.6695130.122*0.796 (18)
C15B0.5231 (10)0.369 (4)0.652 (3)0.076 (8)0.204 (18)
H15C0.4906770.3535800.6290110.091*0.204 (18)
H15D0.5271850.5008330.7225700.091*0.204 (18)
C160.5411 (4)0.1346 (18)0.7248 (12)0.115 (3)
H16A0.5079610.1500760.7251870.138*0.796 (18)
H16B0.5493600.0002510.6602360.138*0.796 (18)
H16C0.5164250.0195130.7129490.138*0.204 (18)
H16D0.5655330.0805550.6577520.138*0.204 (18)
C170.5590 (5)0.098 (3)0.8888 (13)0.147 (5)
H17A0.5780340.2315400.9170030.221*
H17B0.5766430.0465020.8933440.221*
H17C0.5336570.0874640.9587650.221*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.063 (3)0.037 (2)0.039 (2)0.0047 (18)0.006 (2)0.009 (2)
O20.081 (3)0.047 (3)0.079 (3)0.006 (2)0.014 (3)0.031 (3)
O30.069 (3)0.046 (3)0.076 (4)0.001 (2)0.006 (3)0.016 (3)
C20.077 (5)0.035 (3)0.047 (4)0.004 (3)0.014 (3)0.001 (3)
C30.065 (4)0.040 (3)0.050 (4)0.009 (3)0.004 (3)0.004 (3)
C40.063 (5)0.042 (3)0.048 (4)0.012 (3)0.005 (3)0.005 (3)
C50.077 (5)0.035 (3)0.049 (4)0.004 (3)0.002 (4)0.020 (3)
C60.080 (5)0.037 (3)0.047 (4)0.001 (4)0.003 (4)0.018 (3)
C70.060 (4)0.036 (3)0.044 (4)0.001 (3)0.003 (3)0.005 (3)
C80.069 (4)0.027 (3)0.035 (3)0.003 (3)0.000 (3)0.003 (3)
C90.069 (4)0.030 (3)0.026 (3)0.004 (3)0.005 (3)0.005 (3)
C100.058 (4)0.036 (3)0.030 (3)0.009 (3)0.000 (3)0.006 (3)
C110.077 (5)0.057 (4)0.079 (5)0.016 (4)0.002 (4)0.025 (4)
C120.072 (5)0.046 (4)0.054 (4)0.002 (3)0.000 (3)0.016 (3)
C130.082 (5)0.059 (4)0.099 (5)0.015 (4)0.024 (4)0.024 (4)
C140.127 (8)0.081 (5)0.107 (5)0.017 (5)0.042 (5)0.015 (4)
C15A0.132 (11)0.063 (5)0.110 (5)0.002 (6)0.011 (6)0.013 (5)
C15B0.072 (17)0.064 (12)0.090 (10)0.026 (11)0.010 (9)0.001 (9)
C160.146 (8)0.091 (6)0.109 (7)0.001 (5)0.011 (6)0.024 (5)
C170.136 (10)0.180 (12)0.125 (8)0.008 (9)0.003 (7)0.047 (8)
Geometric parameters (Å, º) top
O1—C21.375 (8)C12—H12C0.9600
O1—C91.375 (7)C13—H13A0.9700
O2—C21.220 (7)C13—H13B0.9700
O3—H30.8200C13—C141.501 (9)
O3—C71.347 (8)C14—H14A0.9700
C2—C31.446 (9)C14—H14B0.9700
C3—C41.371 (9)C14—H14C0.9700
C3—C131.497 (11)C14—H14D0.9700
C4—C101.416 (9)C14—C15A1.486 (10)
C4—C111.515 (9)C14—C15B1.529 (12)
C5—H50.9300C15A—H15A0.9700
C5—C61.359 (8)C15A—H15B0.9700
C5—C101.410 (9)C15A—C161.552 (10)
C6—H60.9300C15B—H15C0.9700
C6—C71.407 (8)C15B—H15D0.9700
C7—C81.386 (8)C15B—C161.546 (13)
C8—C91.384 (8)C16—H16A0.9700
C8—C121.498 (9)C16—H16B0.9700
C9—C101.400 (8)C16—H16C0.9700
C11—H11A0.9600C16—H16D0.9700
C11—H11B0.9600C16—C171.531 (11)
C11—H11C0.9600C17—H17A0.9600
C12—H12A0.9600C17—H17B0.9600
C12—H12B0.9600C17—H17C0.9600
C9—O1—C2121.9 (5)C14—C13—H13A108.1
C7—O3—H3109.5C14—C13—H13B108.1
O1—C2—C3119.3 (5)C13—C14—H14A108.4
O2—C2—O1115.4 (6)C13—C14—H14B108.4
O2—C2—C3125.3 (6)C13—C14—H14C103.7
C2—C3—C13116.4 (6)C13—C14—H14D103.7
C4—C3—C2118.7 (6)C13—C14—C15B134.0 (12)
C4—C3—C13124.8 (6)H14A—C14—H14B107.5
C3—C4—C10121.0 (5)H14C—C14—H14D105.4
C3—C4—C11120.3 (6)C15A—C14—C13115.4 (9)
C10—C4—C11118.7 (5)C15A—C14—H14A108.4
C6—C5—H5119.1C15A—C14—H14B108.4
C6—C5—C10121.9 (6)C15B—C14—H14C103.7
C10—C5—H5119.1C15B—C14—H14D103.7
C5—C6—H6119.8C14—C15A—H15A109.5
C5—C6—C7120.3 (6)C14—C15A—H15B109.5
C7—C6—H6119.8C14—C15A—C16110.9 (9)
O3—C7—C6121.1 (5)H15A—C15A—H15B108.1
O3—C7—C8118.4 (5)C16—C15A—H15A109.5
C8—C7—C6120.5 (6)C16—C15A—H15B109.5
C7—C8—C12120.7 (6)C14—C15B—H15C109.9
C9—C8—C7117.1 (5)C14—C15B—H15D109.9
C9—C8—C12122.2 (5)C14—C15B—C16108.9 (11)
O1—C9—C8115.7 (5)H15C—C15B—H15D108.3
O1—C9—C10119.7 (5)C16—C15B—H15C109.9
C8—C9—C10124.6 (5)C16—C15B—H15D109.9
C5—C10—C4125.1 (5)C15A—C16—H16A110.5
C9—C10—C4119.4 (5)C15A—C16—H16B110.5
C9—C10—C5115.5 (6)C15B—C16—H16C105.4
C4—C11—H11A109.5C15B—C16—H16D105.4
C4—C11—H11B109.5H16A—C16—H16B108.7
C4—C11—H11C109.5H16C—C16—H16D106.0
H11A—C11—H11B109.5C17—C16—C15A106.2 (10)
H11A—C11—H11C109.5C17—C16—C15B127.7 (17)
H11B—C11—H11C109.5C17—C16—H16A110.5
C8—C12—H12A109.5C17—C16—H16B110.5
C8—C12—H12B109.5C17—C16—H16C105.4
C8—C12—H12C109.5C17—C16—H16D105.4
H12A—C12—H12B109.5C16—C17—H17A109.5
H12A—C12—H12C109.5C16—C17—H17B109.5
H12B—C12—H12C109.5C16—C17—H17C109.5
C3—C13—H13A108.1H17A—C17—H17B109.5
C3—C13—H13B108.1H17A—C17—H17C109.5
C3—C13—C14116.6 (8)H17B—C17—H17C109.5
H13A—C13—H13B107.3
O1—C2—C3—C41.0 (9)C6—C5—C10—C91.4 (10)
O1—C2—C3—C13179.2 (6)C6—C7—C8—C91.1 (9)
O1—C9—C10—C40.2 (8)C6—C7—C8—C12179.8 (6)
O1—C9—C10—C5179.5 (6)C7—C8—C9—O1179.6 (5)
O2—C2—C3—C4179.5 (6)C7—C8—C9—C100.9 (9)
O2—C2—C3—C132.2 (10)C8—C9—C10—C4179.3 (6)
O3—C7—C8—C9179.5 (5)C8—C9—C10—C51.1 (9)
O3—C7—C8—C120.4 (9)C9—O1—C2—O2179.7 (5)
C2—O1—C9—C8179.9 (5)C9—O1—C2—C31.0 (8)
C2—O1—C9—C100.4 (8)C10—C5—C6—C71.6 (11)
C2—C3—C4—C100.4 (9)C11—C4—C10—C52.5 (9)
C2—C3—C4—C11178.3 (6)C11—C4—C10—C9177.8 (6)
C2—C3—C13—C14100.1 (8)C12—C8—C9—O10.5 (8)
C3—C4—C10—C5179.4 (7)C12—C8—C9—C10180.0 (6)
C3—C4—C10—C90.2 (9)C13—C3—C4—C10178.4 (6)
C3—C13—C14—C15A75.1 (10)C13—C3—C4—C113.6 (11)
C3—C13—C14—C15B128 (2)C13—C14—C15A—C1674.0 (13)
C4—C3—C13—C1478.0 (10)C13—C14—C15B—C1632 (4)
C5—C6—C7—O3179.2 (6)C14—C15A—C16—C17178.2 (11)
C5—C6—C7—C81.5 (10)C14—C15B—C16—C17125.6 (19)
C6—C5—C10—C4179.0 (6)
 

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