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—HO 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 (pSupporting information

CCDC references: 2158229; 2158230

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).

Crystal data C24H22N2O3·[+solvents]Dx = 1.090 Mg m−3Mr = 386.43Mo Kα radiation, λ = 0.71073 ÅTrigonal, R3Cell parameters from 1475 reflectionsa = 49.850 (7) Åθ = 2.2–18.7°c = 4.9234 (8) ŵ = 0.07 mm−1V = 10596 (3) Å3T = 296 KZ = 18Plate, colourlessF(000) = 36720.26 × 0.10 × 0.09 mm Data collection Bruker APEX-II CCD
diffractometer4177 independent reflectionsRadiation source: microfocus sealed X-ray tube, Incoatec Iµs1911 reflections with I > 2σ(I)Mirror optics monochromatorRint = 0.061Detector resolution: 7.9 pixels mm-1θmax = 25.1°, θmin = 0.8°φ and ω scansh = −37→59Absorption correction: multi-scan
SADABS V2014/4 (Bruker AXS)k = −58→48Tmin = 0.393, Tmax = 0.746l = −5→513237 measured reflections Refinement Refinement on F2Primary atom site location: dualLeast-squares matrix: fullHydrogen site location: inferred from neighbouring sitesR[F2 > 2σ(F2)] = 0.110H-atom parameters constrainedwR(F2) = 0.378 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3S = 1.15(Δ/σ)max < 0.0014177 reflectionsΔρmax = 0.42 e Å−3294 parametersΔρmin = −0.29 e Å−3290 restraints Special details

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) 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)H13A0.5040350.657885−0.0767260.126*H13B0.5371130.681720−0.1851930.126*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)H15A0.5135500.715891−0.2563250.180*0.558 (8)H15B0.4832370.688739−0.1294350.180*0.558 (8)C15B0.5127 (5)0.7208 (4)−0.035 (5)0.146 (3)0.442 (8)H15C0.5243530.728795−0.2024670.175*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)H16C0.4773510.687481−0.2523800.193*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)H17A0.4685360.724399−0.3150500.243*0.558 (8)H17B0.4919410.759520−0.2598840.243*0.558 (8)H17C0.4614110.742095−0.0888780.243*0.558 (8)C17B0.4579 (5)0.7127 (5)−0.136 (5)0.162 (3)0.442 (8)H17D0.4602430.720262−0.3186210.243*0.442 (8)H17E0.4633130.729385−0.0107930.243*0.442 (8)H17F0.4367970.696826−0.1063610.243*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) U11U22U33U12U13U23O10.096 (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) O1—C21.363 (8)C14—H14D0.9700O1—C91.381 (6)C14—C15A1.540 (8)O2—C21.218 (7)C14—C15B1.480 (15)O3—C71.409 (6)C15A—H15A0.9700O3—C181.362 (6)C15A—H15B0.9700N1—C241.154 (6)C15A—C16A1.520 (9)N2—C251.151 (7)C15B—H15C0.9700C2—C31.435 (9)C15B—H15D0.9700C3—C41.365 (8)C15B—C16B1.507 (17)C3—C131.508 (8)C16A—H16A0.9700C4—C101.457 (8)C16A—H16B0.9700C4—C111.488 (8)C16A—C17A1.537 (9)C5—H50.9300C16B—H16C0.9700C5—C61.354 (7)C16B—H16D0.9700C5—C101.403 (7)C16B—C17B1.501 (17)C6—H60.9300C17A—H17A0.9600C6—C71.379 (7)C17A—H17B0.9600C7—C81.370 (7)C17A—H17C0.9600C8—C91.387 (8)C17B—H17D0.9600C8—C121.515 (8)C17B—H17E0.9600C9—C101.376 (8)C17B—H17F0.9600C11—H11A0.9600C18—C191.396 (6)C11—H11B0.9600C18—C231.381 (7)C11—H11C0.9600C19—H190.9300C12—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—H220.9300C14—H14A0.9700C22—C231.348 (7)C14—H14B0.9700C23—H230.9300C14—H14C0.9700 C2—O1—C9121.2 (5)C15B—C14—H14D106.0C18—O3—C7120.2 (4)C14—C15A—H15A109.2O1—C2—C3119.6 (6)C14—C15A—H15B109.2O2—C2—O1114.2 (7)H15A—C15A—H15B107.9O2—C2—C3126.2 (7)C16A—C15A—C14112.0 (8)C2—C3—C13116.8 (6)C16A—C15A—H15A109.2C4—C3—C2120.6 (6)C16A—C15A—H15B109.2C4—C3—C13122.6 (7)C14—C15B—H15C111.1C3—C4—C10118.3 (6)C14—C15B—H15D111.1C3—C4—C11122.9 (6)C14—C15B—C16B103.2 (13)C10—C4—C11118.8 (5)H15C—C15B—H15D109.1C6—C5—H5119.6C16B—C15B—H15C111.1C6—C5—C10120.7 (5)C16B—C15B—H15D111.1C10—C5—H5119.6C15A—C16A—H16A109.5C5—C6—H6120.3C15A—C16A—H16B109.5C5—C6—C7119.4 (5)C15A—C16A—C17A110.6 (8)C7—C6—H6120.3H16A—C16A—H16B108.1C6—C7—O3120.1 (5)C17A—C16A—H16A109.5C8—C7—O3116.8 (5)C17A—C16A—H16B109.5C8—C7—C6123.0 (5)C15B—C16B—H16C107.4C7—C8—C9115.7 (5)C15B—C16B—H16D107.4C7—C8—C12122.0 (6)H16C—C16B—H16D106.9C9—C8—C12122.3 (5)C17B—C16B—C15B119.9 (17)O1—C9—C8115.5 (5)C17B—C16B—H16C107.4C10—C9—O1120.6 (5)C17B—C16B—H16D107.4C10—C9—C8123.9 (5)C16A—C17A—H17A109.5C5—C10—C4123.2 (5)C16A—C17A—H17B109.5C9—C10—C4119.7 (5)C16A—C17A—H17C109.5C9—C10—C5117.2 (5)H17A—C17A—H17B109.5C4—C11—H11A109.5H17A—C17A—H17C109.5C4—C11—H11B109.5H17B—C17A—H17C109.5C4—C11—H11C109.5C16B—C17B—H17D109.5H11A—C11—H11B109.5C16B—C17B—H17E109.5H11A—C11—H11C109.5C16B—C17B—H17F109.5H11B—C11—H11C109.5H17D—C17B—H17E109.5C8—C12—H12A109.5H17D—C17B—H17F109.5C8—C12—H12B109.5H17E—C17B—H17F109.5C8—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—H19120.5C3—C13—H13A109.0C20—C19—C18119.0 (5)C3—C13—H13B109.0C20—C19—H19120.5C3—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—H22119.2C13—C14—H14D106.0C23—C22—C21121.6 (5)C13—C14—C15A106.1 (6)C23—C22—H22119.2H14A—C14—H14B108.7C18—C23—H23120.0H14C—C14—H14D106.3C22—C23—C18120.0 (5)C15A—C14—H14A110.5C22—C23—H23120.0C15A—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—C10−2.9 (7)O1—C2—C3—C13−178.1 (5)C8—C9—C10—C4−177.3 (5)O1—C9—C10—C40.7 (7)C8—C9—C10—C53.3 (7)O1—C9—C10—C5−178.6 (4)C9—O1—C2—O2178.7 (4)O2—C2—C3—C4179.1 (6)C9—O1—C2—C3−2.3 (8)O2—C2—C3—C130.7 (9)C10—C5—C6—C7−1.7 (7)O3—C7—C8—C9−176.4 (4)C11—C4—C10—C5−4.5 (7)O3—C7—C8—C123.2 (7)C11—C4—C10—C9176.2 (5)O3—C18—C19—C20179.6 (5)C12—C8—C9—O1−0.6 (7)O3—C18—C23—C22−178.9 (5)C12—C8—C9—C10177.5 (5)C2—O1—C9—C8180.0 (5)C13—C3—C4—C10−179.5 (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—C11−176.7 (5)C13—C14—C15B—C16B70 (2)C2—C3—C13—C14−93.4 (8)C14—C15A—C16A—C17A174.6 (15)C3—C4—C10—C5176.7 (4)C14—C15B—C16B—C17B157 (2)C3—C4—C10—C9−2.6 (7)C18—O3—C7—C656.2 (6)C3—C13—C14—C15A−170.4 (10)C18—O3—C7—C8−127.1 (5)C3—C13—C14—C15B172.1 (12)C18—C19—C20—C21−2.5 (7)C4—C3—C13—C1488.1 (7)C18—C19—C20—C24177.4 (5)C5—C6—C7—O3178.6 (4)C19—C18—C23—C22−0.5 (8)C5—C6—C7—C82.1 (7)C19—C20—C21—C222.8 (7)C6—C5—C10—C4179.7 (4)C19—C20—C21—C25−178.2 (5)C6—C5—C10—C9−0.9 (7)C20—C21—C22—C23−2.0 (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—C22−177.1 (5)C7—O3—C18—C23−173.1 (4)C24—C20—C21—C251.9 (7)C7—C8—C9—O1179.0 (4)C25—C21—C22—C23179.0 (5) Crystal data C16H20O3Dx = 1.220 Mg m−3Mr = 260.32Mo Kα radiation, λ = 0.71073 ÅOrthorhombic, Pca21Cell parameters from 1711 reflectionsa = 29.189 (8) Åθ = 2.7–22.6°b = 5.5877 (15) ŵ = 0.08 mm−1c = 8.686 (3) ÅT = 298 KV = 1416.7 (7) Å3Block, colourlessZ = 40.19 × 0.14 × 0.10 mmF(000) = 560 Data collection Bruker APEX-II CCD
diffractometer2415 independent reflectionsRadiation source: microfocus sealed X-ray tube, Incoatec Iµs1700 reflections with I > 2σ(I)Mirror optics monochromatorRint = 0.057Detector resolution: 7.9 pixels mm-1θmax = 25.0°, θmin = 1.4°ω and φ scansh = −34→32Absorption correction: multi-scan
SADABS V2014/4 (Bruker AXS)k = −6→6Tmin = 0.393, Tmax = 0.746l = −10→106701 measured reflections Refinement Refinement on F2Hydrogen site location: inferred from neighbouring sitesLeast-squares matrix: fullH-atom parameters constrainedR[F2 > 2σ(F2)] = 0.074 w = 1/[σ2(Fo2) + (0.1144P)2 + 0.4608P]
where P = (Fo2 + 2Fc2)/3wR(F2) = 0.211(Δ/σ)max < 0.001S = 1.05Δρmax = 0.28 e Å−32415 reflectionsΔρmin = −0.25 e Å−3186 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)