Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623003704/ov3165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229623003704/ov3165mPMIpCH3sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229623003704/ov3165mAApCH3sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623003704/ov3165mPMIpCH3sup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623003704/ov3165mAApCH3sup5.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229623003704/ov3165sup6.pdf |
CCDC references: 2029949; 2029928
For both structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2001), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: X-SEED (Barbour, 2001).
C24H21NO | F(000) = 1440 |
Mr = 339.42 | Dx = 1.253 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
a = 19.5522 (13) Å | Cell parameters from 4400 reflections |
b = 5.8693 (4) Å | θ = 2.8–68.3° |
c = 31.3714 (19) Å | µ = 0.59 mm−1 |
β = 91.438 (4)° | T = 100 K |
V = 3599.0 (4) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.11 × 0.03 mm |
Bruker D8 Venture diffractometer | 3283 independent reflections |
Radiation source: Microsource IuS Incoatec 3.0 | 2526 reflections with I > 2σ(I) |
Double Bounce Multilayer Mirrors monochromator | Rint = 0.043 |
Detector resolution: 7.9 pixels mm-1 | θmax = 68.3°, θmin = 4.5° |
φ and ω scans | h = −22→23 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −6→7 |
Tmin = 0.684, Tmax = 0.753 | l = −37→37 |
10519 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0423P)2 + 2.4974P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3283 reflections | Δρmax = 0.17 e Å−3 |
237 parameters | Δρmin = −0.17 e Å−3 |
0 restraints |
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. |
Refinement. All C-H hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). The X-ray intensity data for each chalcone derivative was measured at 100 K on a Bruker Photon II D8 Venture diffractometer equipped with both IµS-Cu and IµS-Mo microfocus X-ray sources. The Cu Kα (λ = 1.54178 Å) source was used for all crystallographic investigations. Data sets were corrected for Lorentz and polarization effects as well as absorption. The criterion for observed reflections was I > 2σ(I). Lattice parameters were determined from least-squares analysis and reflection data. Empirical absorption corrections were applied using SADABS. Structures were solved by direct methods and refined by full-matrix least-squares analysis on F2 using X-SEED equipped with SHELXT (Barbour, 2001; Sheldrick, 2015a). All non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F2 using the SHELXL program (Sheldrick, 2015b). Unit-cell projections were visualized with Mercury 2020.1 (Macrae et al., 2020), Hirshfeld analyses were executed with CrystalExplorer17.5 (Turner et al., 2017), while distance/angle measurements, as well as ORTEP images, were captured using OLEX2 (Dolomanov et al., 2009). Electrostatic potential calculations employed GAUSSIAN09 (Frisch et al., 2009). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49474 (6) | 0.52779 (19) | 0.65074 (3) | 0.0298 (3) | |
N1 | 0.35087 (7) | 0.5081 (2) | 0.51350 (4) | 0.0267 (3) | |
C1 | 0.48027 (8) | 0.3248 (3) | 0.64654 (5) | 0.0237 (3) | |
C2 | 0.51253 (8) | 0.1489 (3) | 0.67399 (5) | 0.0252 (4) | |
H2 | 0.493799 | −0.000423 | 0.674354 | 0.030* | |
C3 | 0.56766 (8) | 0.1966 (3) | 0.69831 (5) | 0.0238 (3) | |
H3 | 0.585393 | 0.346729 | 0.696026 | 0.029* | |
C4 | 0.42985 (8) | 0.2539 (3) | 0.61228 (5) | 0.0219 (3) | |
C5 | 0.41504 (8) | 0.4089 (3) | 0.57967 (5) | 0.0232 (3) | |
H5 | 0.436777 | 0.553701 | 0.579918 | 0.028* | |
C6 | 0.36870 (8) | 0.3544 (3) | 0.54667 (5) | 0.0243 (4) | |
C7 | 0.33446 (9) | 0.1452 (3) | 0.54769 (5) | 0.0282 (4) | |
H7 | 0.301087 | 0.108959 | 0.526220 | 0.034* | |
C8 | 0.34926 (9) | −0.0086 (3) | 0.57997 (5) | 0.0284 (4) | |
H8 | 0.326314 | −0.151290 | 0.580274 | 0.034* | |
C9 | 0.39731 (8) | 0.0425 (3) | 0.61208 (5) | 0.0247 (3) | |
H9 | 0.407876 | −0.066126 | 0.633713 | 0.030* | |
C10 | 0.60389 (8) | 0.0446 (3) | 0.72806 (5) | 0.0223 (3) | |
C11 | 0.66169 (8) | 0.1229 (3) | 0.75075 (5) | 0.0253 (4) | |
H11 | 0.678902 | 0.270849 | 0.745028 | 0.030* | |
C12 | 0.69437 (8) | −0.0108 (3) | 0.78141 (5) | 0.0256 (4) | |
H12 | 0.733766 | 0.046423 | 0.796165 | 0.031* | |
C13 | 0.67045 (8) | −0.2271 (3) | 0.79092 (5) | 0.0246 (4) | |
C14 | 0.61319 (8) | −0.3070 (3) | 0.76779 (5) | 0.0252 (4) | |
H14 | 0.595879 | −0.454531 | 0.773765 | 0.030* | |
C15 | 0.58130 (8) | −0.1770 (3) | 0.73656 (5) | 0.0242 (3) | |
H15 | 0.543627 | −0.238174 | 0.720646 | 0.029* | |
C16 | 0.39784 (8) | 0.6276 (3) | 0.49703 (5) | 0.0276 (4) | |
H16 | 0.443977 | 0.601924 | 0.505962 | 0.033* | |
C17 | 0.38331 (8) | 0.8029 (3) | 0.46486 (5) | 0.0260 (4) | |
C18 | 0.31642 (8) | 0.8442 (3) | 0.44997 (5) | 0.0262 (4) | |
H18 | 0.279837 | 0.753635 | 0.459890 | 0.031* | |
C19 | 0.30344 (8) | 1.0161 (3) | 0.42093 (5) | 0.0262 (4) | |
H19 | 0.257753 | 1.042095 | 0.411094 | 0.031* | |
C20 | 0.35566 (8) | 1.1524 (3) | 0.40567 (5) | 0.0264 (4) | |
C21 | 0.42239 (9) | 1.1103 (3) | 0.42046 (5) | 0.0313 (4) | |
H21 | 0.458911 | 1.200764 | 0.410430 | 0.038* | |
C22 | 0.43590 (8) | 0.9378 (3) | 0.44961 (5) | 0.0306 (4) | |
H22 | 0.481619 | 0.911197 | 0.459317 | 0.037* | |
C23 | 0.34029 (9) | 1.3399 (3) | 0.37409 (5) | 0.0339 (4) | |
H23A | 0.350244 | 1.286856 | 0.345283 | 0.051* | |
H23B | 0.368749 | 1.472967 | 0.381026 | 0.051* | |
H23C | 0.291888 | 1.382030 | 0.375406 | 0.051* | |
C24 | 0.70477 (9) | −0.3717 (3) | 0.82490 (5) | 0.0308 (4) | |
H24A | 0.731695 | −0.491419 | 0.811428 | 0.046* | |
H24B | 0.669920 | −0.441575 | 0.842616 | 0.046* | |
H24C | 0.735007 | −0.276230 | 0.842739 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0368 (7) | 0.0227 (6) | 0.0295 (6) | −0.0030 (5) | −0.0101 (5) | 0.0012 (5) |
N1 | 0.0328 (8) | 0.0266 (7) | 0.0203 (6) | 0.0056 (6) | −0.0060 (6) | −0.0014 (6) |
C1 | 0.0249 (8) | 0.0244 (8) | 0.0216 (8) | −0.0004 (7) | −0.0011 (6) | 0.0018 (6) |
C2 | 0.0281 (8) | 0.0229 (8) | 0.0244 (8) | −0.0019 (7) | −0.0053 (6) | 0.0017 (6) |
C3 | 0.0272 (8) | 0.0226 (8) | 0.0216 (7) | −0.0020 (7) | −0.0002 (6) | 0.0004 (6) |
C4 | 0.0218 (8) | 0.0225 (8) | 0.0211 (7) | 0.0036 (6) | −0.0020 (6) | −0.0017 (6) |
C5 | 0.0252 (8) | 0.0217 (8) | 0.0226 (7) | 0.0035 (7) | −0.0029 (6) | −0.0011 (6) |
C6 | 0.0264 (8) | 0.0244 (8) | 0.0220 (8) | 0.0082 (7) | −0.0030 (6) | −0.0021 (6) |
C7 | 0.0311 (9) | 0.0266 (9) | 0.0264 (8) | 0.0046 (7) | −0.0090 (7) | −0.0057 (7) |
C8 | 0.0296 (9) | 0.0228 (8) | 0.0324 (9) | 0.0001 (7) | −0.0068 (7) | −0.0029 (7) |
C9 | 0.0267 (8) | 0.0225 (8) | 0.0246 (8) | 0.0033 (7) | −0.0034 (6) | −0.0001 (6) |
C10 | 0.0229 (8) | 0.0246 (8) | 0.0194 (7) | 0.0015 (7) | −0.0002 (6) | −0.0004 (6) |
C11 | 0.0270 (8) | 0.0213 (8) | 0.0275 (8) | −0.0015 (7) | −0.0024 (6) | 0.0003 (6) |
C12 | 0.0239 (8) | 0.0273 (9) | 0.0252 (8) | 0.0010 (7) | −0.0069 (6) | −0.0037 (7) |
C13 | 0.0274 (8) | 0.0278 (9) | 0.0187 (7) | 0.0053 (7) | −0.0015 (6) | −0.0006 (6) |
C14 | 0.0277 (8) | 0.0219 (8) | 0.0260 (8) | −0.0010 (7) | −0.0001 (7) | 0.0005 (7) |
C15 | 0.0236 (8) | 0.0255 (8) | 0.0232 (8) | −0.0003 (7) | −0.0040 (6) | −0.0020 (7) |
C16 | 0.0254 (8) | 0.0372 (10) | 0.0200 (8) | 0.0103 (8) | −0.0036 (6) | −0.0018 (7) |
C17 | 0.0273 (8) | 0.0331 (9) | 0.0175 (7) | 0.0071 (7) | −0.0009 (6) | −0.0021 (7) |
C18 | 0.0248 (8) | 0.0319 (9) | 0.0219 (8) | 0.0005 (7) | −0.0030 (6) | −0.0021 (7) |
C19 | 0.0247 (8) | 0.0326 (9) | 0.0209 (7) | 0.0046 (7) | −0.0057 (6) | −0.0033 (7) |
C20 | 0.0298 (9) | 0.0309 (9) | 0.0186 (7) | 0.0051 (7) | −0.0016 (6) | −0.0022 (7) |
C21 | 0.0265 (9) | 0.0423 (10) | 0.0250 (8) | 0.0001 (8) | 0.0001 (7) | 0.0041 (7) |
C22 | 0.0232 (8) | 0.0454 (11) | 0.0230 (8) | 0.0062 (8) | −0.0006 (6) | 0.0018 (7) |
C23 | 0.0367 (10) | 0.0362 (10) | 0.0285 (9) | 0.0032 (8) | −0.0035 (7) | 0.0040 (8) |
C24 | 0.0358 (10) | 0.0303 (9) | 0.0258 (8) | 0.0047 (8) | −0.0064 (7) | 0.0032 (7) |
O1—C1 | 1.231 (2) | C13—C14 | 1.400 (2) |
N1—C16 | 1.275 (2) | C13—C24 | 1.507 (2) |
N1—C6 | 1.414 (2) | C14—C15 | 1.379 (2) |
C1—C2 | 1.476 (2) | C14—H14 | 0.9500 |
C1—C4 | 1.499 (2) | C15—H15 | 0.9500 |
C2—C3 | 1.335 (2) | C16—C17 | 1.464 (2) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—C10 | 1.461 (2) | C17—C22 | 1.392 (2) |
C3—H3 | 0.9500 | C17—C18 | 1.399 (2) |
C4—C5 | 1.394 (2) | C18—C19 | 1.379 (2) |
C4—C9 | 1.395 (2) | C18—H18 | 0.9500 |
C5—C6 | 1.396 (2) | C19—C20 | 1.391 (2) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.399 (2) | C20—C21 | 1.396 (2) |
C7—C8 | 1.382 (2) | C20—C23 | 1.506 (2) |
C7—H7 | 0.9500 | C21—C22 | 1.385 (2) |
C8—C9 | 1.393 (2) | C21—H21 | 0.9500 |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—H9 | 0.9500 | C23—H23A | 0.9800 |
C10—C11 | 1.398 (2) | C23—H23B | 0.9800 |
C10—C15 | 1.401 (2) | C23—H23C | 0.9800 |
C11—C12 | 1.385 (2) | C24—H24A | 0.9800 |
C11—H11 | 0.9500 | C24—H24B | 0.9800 |
C12—C13 | 1.388 (2) | C24—H24C | 0.9800 |
C12—H12 | 0.9500 | ||
C16—N1—C6 | 118.85 (14) | C15—C14—C13 | 121.63 (15) |
O1—C1—C2 | 121.39 (14) | C15—C14—H14 | 119.2 |
O1—C1—C4 | 119.38 (14) | C13—C14—H14 | 119.2 |
C2—C1—C4 | 119.22 (14) | C14—C15—C10 | 120.66 (15) |
C3—C2—C1 | 120.93 (15) | C14—C15—H15 | 119.7 |
C3—C2—H2 | 119.5 | C10—C15—H15 | 119.7 |
C1—C2—H2 | 119.5 | N1—C16—C17 | 122.46 (15) |
C2—C3—C10 | 127.47 (16) | N1—C16—H16 | 118.8 |
C2—C3—H3 | 116.3 | C17—C16—H16 | 118.8 |
C10—C3—H3 | 116.3 | C22—C17—C18 | 118.61 (15) |
C5—C4—C9 | 119.42 (14) | C22—C17—C16 | 120.30 (15) |
C5—C4—C1 | 117.76 (14) | C18—C17—C16 | 121.05 (16) |
C9—C4—C1 | 122.82 (14) | C19—C18—C17 | 120.19 (16) |
C4—C5—C6 | 120.91 (15) | C19—C18—H18 | 119.9 |
C4—C5—H5 | 119.5 | C17—C18—H18 | 119.9 |
C6—C5—H5 | 119.5 | C18—C19—C20 | 121.58 (15) |
C5—C6—C7 | 119.10 (15) | C18—C19—H19 | 119.2 |
C5—C6—N1 | 122.87 (15) | C20—C19—H19 | 119.2 |
C7—C6—N1 | 117.87 (14) | C19—C20—C21 | 118.12 (15) |
C8—C7—C6 | 119.91 (15) | C19—C20—C23 | 120.70 (15) |
C8—C7—H7 | 120.0 | C21—C20—C23 | 121.17 (16) |
C6—C7—H7 | 120.0 | C22—C21—C20 | 120.68 (16) |
C7—C8—C9 | 120.95 (16) | C22—C21—H21 | 119.7 |
C7—C8—H8 | 119.5 | C20—C21—H21 | 119.7 |
C9—C8—H8 | 119.5 | C21—C22—C17 | 120.82 (16) |
C8—C9—C4 | 119.63 (15) | C21—C22—H22 | 119.6 |
C8—C9—H9 | 120.2 | C17—C22—H22 | 119.6 |
C4—C9—H9 | 120.2 | C20—C23—H23A | 109.5 |
C11—C10—C15 | 117.57 (14) | C20—C23—H23B | 109.5 |
C11—C10—C3 | 119.80 (15) | H23A—C23—H23B | 109.5 |
C15—C10—C3 | 122.56 (14) | C20—C23—H23C | 109.5 |
C12—C11—C10 | 121.34 (15) | H23A—C23—H23C | 109.5 |
C12—C11—H11 | 119.3 | H23B—C23—H23C | 109.5 |
C10—C11—H11 | 119.3 | C13—C24—H24A | 109.5 |
C11—C12—C13 | 121.03 (15) | C13—C24—H24B | 109.5 |
C11—C12—H12 | 119.5 | H24A—C24—H24B | 109.5 |
C13—C12—H12 | 119.5 | C13—C24—H24C | 109.5 |
C12—C13—C14 | 117.69 (14) | H24A—C24—H24C | 109.5 |
C12—C13—C24 | 121.39 (15) | H24B—C24—H24C | 109.5 |
C14—C13—C24 | 120.93 (15) | ||
O1—C1—C2—C3 | −13.4 (2) | C3—C10—C11—C12 | 175.32 (14) |
C4—C1—C2—C3 | 165.41 (14) | C10—C11—C12—C13 | −0.5 (2) |
C1—C2—C3—C10 | 177.79 (14) | C11—C12—C13—C14 | 1.4 (2) |
O1—C1—C4—C5 | 16.6 (2) | C11—C12—C13—C24 | −178.65 (15) |
C2—C1—C4—C5 | −162.19 (14) | C12—C13—C14—C15 | 0.1 (2) |
O1—C1—C4—C9 | −162.82 (15) | C24—C13—C14—C15 | −179.88 (15) |
C2—C1—C4—C9 | 18.4 (2) | C13—C14—C15—C10 | −2.4 (2) |
C9—C4—C5—C6 | −0.7 (2) | C11—C10—C15—C14 | 3.3 (2) |
C1—C4—C5—C6 | 179.86 (14) | C3—C10—C15—C14 | −173.79 (14) |
C4—C5—C6—C7 | 3.1 (2) | C6—N1—C16—C17 | −175.29 (14) |
C4—C5—C6—N1 | 178.44 (14) | N1—C16—C17—C22 | 176.32 (16) |
C16—N1—C6—C5 | 41.8 (2) | N1—C16—C17—C18 | −1.3 (2) |
C16—N1—C6—C7 | −142.73 (16) | C22—C17—C18—C19 | −0.3 (2) |
C5—C6—C7—C8 | −3.2 (2) | C16—C17—C18—C19 | 177.41 (15) |
N1—C6—C7—C8 | −178.77 (15) | C17—C18—C19—C20 | 0.0 (2) |
C6—C7—C8—C9 | 0.9 (2) | C18—C19—C20—C21 | 0.3 (2) |
C7—C8—C9—C4 | 1.5 (2) | C18—C19—C20—C23 | −179.74 (15) |
C5—C4—C9—C8 | −1.7 (2) | C19—C20—C21—C22 | −0.2 (2) |
C1—C4—C9—C8 | 177.80 (14) | C23—C20—C21—C22 | 179.80 (16) |
C2—C3—C10—C11 | 179.24 (16) | C20—C21—C22—C17 | −0.1 (3) |
C2—C3—C10—C15 | −3.8 (3) | C18—C17—C22—C21 | 0.3 (2) |
C15—C10—C11—C12 | −1.8 (2) | C16—C17—C22—C21 | −177.37 (15) |
C18H17NO2 | F(000) = 1184 |
Mr = 279.32 | Dx = 1.306 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
a = 25.1922 (5) Å | Cell parameters from 9920 reflections |
b = 5.7621 (1) Å | θ = 3.7–72.1° |
c = 20.7012 (4) Å | µ = 0.68 mm−1 |
β = 109.066 (1)° | T = 100 K |
V = 2840.14 (9) Å3 | Prism, colourless |
Z = 8 | 0.46 × 0.17 × 0.15 mm |
Bruker D8 Venture diffractometer | 2786 independent reflections |
Radiation source: Microsource IuS Incoatec 3.0 | 2596 reflections with I > 2σ(I) |
Double Bounce Multilayer Mirrors monochromator | Rint = 0.025 |
Detector resolution: 7.9 pixels mm-1 | θmax = 72.2°, θmin = 3.7° |
φ and ω scans | h = −30→30 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −7→6 |
Tmin = 0.646, Tmax = 0.754 | l = −25→25 |
14321 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0459P)2 + 2.0674P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2786 reflections | Δρmax = 0.24 e Å−3 |
195 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
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. |
Refinement. All C-H hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). The H atom attached to nitrogen N1 was located in Fourier diff map and assigned Uiso = 1.2xUeqiv. The X-ray intensity data for each chalcone derivative was measured at 100 K on a Bruker Photon II D8 Venture diffractometer equipped with both IµS-Cu and IµS-Mo microfocus X-ray sources. The Cu Kα (λ = 1.54178 Å) source was used for all crystallographic investigations. Data sets were corrected for Lorentz and polarization effects as well as absorption. The criterion for observed reflections was I > 2σ(I). Lattice parameters were determined from least-squares analysis and reflection data. Empirical absorption corrections were applied using SADABS. Structures were solved by direct methods and refined by full-matrix least-squares analysis on F2 using X-SEED equipped with SHELXT (Barbour, 2001; Sheldrick, 2015a). All non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F2 using the SHELXL program (Sheldrick, 2015b). Unit-cell projections were visualized with Mercury 2020.1 (Macrae et al., 2020), Hirshfeld analyses were executed with CrystalExplorer17.5 (Turner et al., 2017), while distance/angle measurements, as well as ORTEP images, were captured using OLEX2 (Dolomanov et al., 2009). Electrostatic potential calculations employed GAUSSIAN09 (Frisch et al., 2009). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.46820 (3) | 0.81616 (14) | 0.39168 (4) | 0.0250 (2) | |
O2 | 0.72479 (3) | 0.81750 (17) | 0.64907 (4) | 0.0312 (2) | |
N1 | 0.63056 (4) | 0.88412 (16) | 0.60966 (4) | 0.0186 (2) | |
HN1 | 0.6047 (6) | 0.979 (3) | 0.6119 (7) | 0.028* | |
C1 | 0.49200 (4) | 0.62787 (19) | 0.39523 (5) | 0.0186 (2) | |
C2 | 0.46888 (4) | 0.4432 (2) | 0.34406 (5) | 0.0206 (2) | |
H2 | 0.485316 | 0.293005 | 0.351190 | 0.025* | |
C3 | 0.42525 (4) | 0.4852 (2) | 0.28807 (5) | 0.0197 (2) | |
H3 | 0.410823 | 0.638878 | 0.283304 | 0.024* | |
C4 | 0.54573 (4) | 0.58199 (19) | 0.45210 (5) | 0.0172 (2) | |
C5 | 0.56419 (4) | 0.74641 (19) | 0.50440 (5) | 0.0172 (2) | |
H5 | 0.542254 | 0.881225 | 0.503505 | 0.021* | |
C6 | 0.61438 (4) | 0.71465 (19) | 0.55778 (5) | 0.0166 (2) | |
C7 | 0.64652 (4) | 0.51542 (19) | 0.55888 (5) | 0.0188 (2) | |
H7 | 0.680734 | 0.491344 | 0.595127 | 0.023* | |
C8 | 0.62815 (5) | 0.3539 (2) | 0.50687 (6) | 0.0212 (2) | |
H8 | 0.650112 | 0.219210 | 0.507728 | 0.025* | |
C9 | 0.57818 (4) | 0.38495 (19) | 0.45336 (5) | 0.0199 (2) | |
H9 | 0.566228 | 0.272749 | 0.417923 | 0.024* | |
C10 | 0.39684 (4) | 0.32381 (19) | 0.23303 (5) | 0.0181 (2) | |
C11 | 0.34430 (5) | 0.38547 (19) | 0.18694 (5) | 0.0204 (2) | |
H15 | 0.327915 | 0.529786 | 0.192141 | 0.025* | |
C12 | 0.31589 (4) | 0.2384 (2) | 0.13378 (5) | 0.0202 (2) | |
H14 | 0.279916 | 0.282282 | 0.103821 | 0.024* | |
C13 | 0.33906 (4) | 0.02806 (19) | 0.12351 (5) | 0.0191 (2) | |
C14 | 0.39167 (4) | −0.03316 (19) | 0.16940 (5) | 0.0200 (2) | |
H12 | 0.408461 | −0.175418 | 0.163221 | 0.024* | |
C15 | 0.41973 (4) | 0.10988 (19) | 0.22367 (5) | 0.0193 (2) | |
H11 | 0.454871 | 0.062276 | 0.254867 | 0.023* | |
C16 | 0.68404 (4) | 0.9267 (2) | 0.65190 (5) | 0.0192 (2) | |
C17 | 0.68940 (5) | 1.1167 (2) | 0.70315 (6) | 0.0231 (3) | |
H17A | 0.682174 | 1.053758 | 0.743465 | 0.035* | |
H17B | 0.662072 | 1.239254 | 0.682788 | 0.035* | |
H17C | 0.727444 | 1.181338 | 0.716695 | 0.035* | |
C18 | 0.30808 (5) | −0.1296 (2) | 0.06553 (6) | 0.0238 (3) | |
H18A | 0.281767 | −0.226556 | 0.079507 | 0.036* | |
H18B | 0.335026 | −0.228993 | 0.053528 | 0.036* | |
H18C | 0.287275 | −0.036090 | 0.025790 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0218 (4) | 0.0224 (4) | 0.0252 (4) | 0.0049 (3) | 0.0002 (3) | −0.0060 (3) |
O2 | 0.0169 (4) | 0.0408 (5) | 0.0333 (5) | 0.0008 (4) | 0.0047 (3) | −0.0127 (4) |
N1 | 0.0164 (4) | 0.0197 (5) | 0.0187 (4) | 0.0018 (4) | 0.0043 (3) | −0.0025 (4) |
C1 | 0.0178 (5) | 0.0196 (5) | 0.0190 (5) | −0.0002 (4) | 0.0068 (4) | −0.0017 (4) |
C2 | 0.0203 (5) | 0.0182 (5) | 0.0216 (5) | 0.0006 (4) | 0.0046 (4) | −0.0033 (4) |
C3 | 0.0202 (5) | 0.0179 (5) | 0.0210 (5) | −0.0010 (4) | 0.0066 (4) | −0.0019 (4) |
C4 | 0.0167 (5) | 0.0191 (5) | 0.0168 (5) | −0.0012 (4) | 0.0066 (4) | −0.0005 (4) |
C5 | 0.0165 (5) | 0.0168 (5) | 0.0190 (5) | 0.0015 (4) | 0.0068 (4) | 0.0000 (4) |
C6 | 0.0171 (5) | 0.0182 (5) | 0.0159 (5) | −0.0023 (4) | 0.0072 (4) | −0.0005 (4) |
C7 | 0.0175 (5) | 0.0210 (5) | 0.0169 (5) | 0.0019 (4) | 0.0045 (4) | 0.0032 (4) |
C8 | 0.0225 (5) | 0.0188 (5) | 0.0228 (5) | 0.0052 (4) | 0.0080 (4) | 0.0009 (4) |
C9 | 0.0221 (5) | 0.0196 (5) | 0.0180 (5) | 0.0007 (4) | 0.0066 (4) | −0.0026 (4) |
C10 | 0.0180 (5) | 0.0192 (5) | 0.0171 (5) | −0.0033 (4) | 0.0057 (4) | −0.0013 (4) |
C11 | 0.0218 (5) | 0.0185 (5) | 0.0208 (5) | 0.0007 (4) | 0.0068 (4) | −0.0001 (4) |
C12 | 0.0182 (5) | 0.0233 (6) | 0.0173 (5) | −0.0027 (4) | 0.0035 (4) | 0.0005 (4) |
C13 | 0.0218 (5) | 0.0211 (6) | 0.0167 (5) | −0.0073 (4) | 0.0093 (4) | −0.0016 (4) |
C14 | 0.0216 (5) | 0.0185 (5) | 0.0224 (5) | −0.0017 (4) | 0.0107 (4) | −0.0022 (4) |
C15 | 0.0162 (5) | 0.0210 (6) | 0.0204 (5) | −0.0007 (4) | 0.0058 (4) | 0.0000 (4) |
C16 | 0.0174 (5) | 0.0235 (6) | 0.0160 (5) | −0.0025 (4) | 0.0046 (4) | 0.0008 (4) |
C17 | 0.0207 (5) | 0.0269 (6) | 0.0204 (5) | −0.0031 (4) | 0.0049 (4) | −0.0034 (4) |
C18 | 0.0270 (6) | 0.0259 (6) | 0.0192 (5) | −0.0082 (5) | 0.0084 (4) | −0.0051 (4) |
O1—C1 | 1.2302 (14) | C9—H9 | 0.9500 |
O2—C16 | 1.2219 (14) | C10—C15 | 1.4010 (15) |
N1—C16 | 1.3675 (13) | C10—C11 | 1.4011 (15) |
N1—C6 | 1.4097 (14) | C11—C12 | 1.3880 (15) |
N1—HN1 | 0.862 (16) | C11—H15 | 0.9500 |
C1—C2 | 1.4800 (15) | C12—C13 | 1.3917 (16) |
C1—C4 | 1.4988 (14) | C12—H14 | 0.9500 |
C2—C3 | 1.3333 (15) | C13—C14 | 1.4003 (15) |
C2—H2 | 0.9500 | C13—C18 | 1.5044 (15) |
C3—C10 | 1.4638 (14) | C14—C15 | 1.3865 (15) |
C3—H3 | 0.9500 | C14—H12 | 0.9500 |
C4—C9 | 1.3943 (15) | C15—H11 | 0.9500 |
C4—C5 | 1.3990 (15) | C16—C17 | 1.4997 (15) |
C5—C6 | 1.3930 (14) | C17—H17A | 0.9800 |
C5—H5 | 0.9500 | C17—H17B | 0.9800 |
C6—C7 | 1.4007 (15) | C17—H17C | 0.9800 |
C7—C8 | 1.3835 (16) | C18—H18A | 0.9800 |
C7—H7 | 0.9500 | C18—H18B | 0.9800 |
C8—C9 | 1.3903 (15) | C18—H18C | 0.9800 |
C8—H8 | 0.9500 | ||
C16—N1—C6 | 126.20 (9) | C11—C10—C3 | 118.81 (10) |
C16—N1—HN1 | 117.2 (10) | C12—C11—C10 | 120.86 (10) |
C6—N1—HN1 | 116.3 (10) | C12—C11—H15 | 119.6 |
O1—C1—C2 | 121.41 (10) | C10—C11—H15 | 119.6 |
O1—C1—C4 | 119.99 (10) | C11—C12—C13 | 121.29 (10) |
C2—C1—C4 | 118.60 (9) | C11—C12—H14 | 119.4 |
C3—C2—C1 | 120.78 (10) | C13—C12—H14 | 119.4 |
C3—C2—H2 | 119.6 | C12—C13—C14 | 117.85 (10) |
C1—C2—H2 | 119.6 | C12—C13—C18 | 120.92 (10) |
C2—C3—C10 | 128.03 (11) | C14—C13—C18 | 121.23 (10) |
C2—C3—H3 | 116.0 | C15—C14—C13 | 121.26 (10) |
C10—C3—H3 | 116.0 | C15—C14—H12 | 119.4 |
C9—C4—C5 | 119.49 (10) | C13—C14—H12 | 119.4 |
C9—C4—C1 | 122.13 (10) | C14—C15—C10 | 120.74 (10) |
C5—C4—C1 | 118.37 (9) | C14—C15—H11 | 119.6 |
C6—C5—C4 | 120.74 (10) | C10—C15—H11 | 119.6 |
C6—C5—H5 | 119.6 | O2—C16—N1 | 123.00 (10) |
C4—C5—H5 | 119.6 | O2—C16—C17 | 121.81 (10) |
C5—C6—C7 | 119.39 (10) | N1—C16—C17 | 115.19 (9) |
C5—C6—N1 | 118.36 (9) | C16—C17—H17A | 109.5 |
C7—C6—N1 | 122.25 (9) | C16—C17—H17B | 109.5 |
C8—C7—C6 | 119.60 (9) | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 120.2 | C16—C17—H17C | 109.5 |
C6—C7—H7 | 120.2 | H17A—C17—H17C | 109.5 |
C7—C8—C9 | 121.28 (10) | H17B—C17—H17C | 109.5 |
C7—C8—H8 | 119.4 | C13—C18—H18A | 109.5 |
C9—C8—H8 | 119.4 | C13—C18—H18B | 109.5 |
C8—C9—C4 | 119.50 (10) | H18A—C18—H18B | 109.5 |
C8—C9—H9 | 120.2 | C13—C18—H18C | 109.5 |
C4—C9—H9 | 120.2 | H18A—C18—H18C | 109.5 |
C15—C10—C11 | 117.97 (10) | H18B—C18—H18C | 109.5 |
C15—C10—C3 | 123.22 (10) | ||
O1—C1—C2—C3 | 8.13 (16) | C5—C4—C9—C8 | 0.53 (16) |
C4—C1—C2—C3 | −171.62 (10) | C1—C4—C9—C8 | 178.84 (10) |
C1—C2—C3—C10 | −179.22 (10) | C2—C3—C10—C15 | −14.93 (17) |
O1—C1—C4—C9 | −171.19 (10) | C2—C3—C10—C11 | 165.48 (11) |
C2—C1—C4—C9 | 8.57 (15) | C15—C10—C11—C12 | 0.12 (15) |
O1—C1—C4—C5 | 7.14 (15) | C3—C10—C11—C12 | 179.73 (10) |
C2—C1—C4—C5 | −173.11 (9) | C10—C11—C12—C13 | −1.50 (16) |
C9—C4—C5—C6 | −0.36 (15) | C11—C12—C13—C14 | 1.20 (15) |
C1—C4—C5—C6 | −178.73 (9) | C11—C12—C13—C18 | −179.68 (10) |
C4—C5—C6—C7 | −0.07 (15) | C12—C13—C14—C15 | 0.46 (15) |
C4—C5—C6—N1 | −179.07 (9) | C18—C13—C14—C15 | −178.65 (9) |
C16—N1—C6—C5 | −156.74 (10) | C13—C14—C15—C10 | −1.84 (16) |
C16—N1—C6—C7 | 24.29 (16) | C11—C10—C15—C14 | 1.52 (15) |
C5—C6—C7—C8 | 0.33 (15) | C3—C10—C15—C14 | −178.07 (10) |
N1—C6—C7—C8 | 179.29 (9) | C6—N1—C16—O2 | −0.32 (17) |
C6—C7—C8—C9 | −0.16 (16) | C6—N1—C16—C17 | −179.59 (10) |
C7—C8—C9—C4 | −0.28 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1i | 0.862 (16) | 2.165 (16) | 3.0213 (12) | 172.3 (14) |
C7—H7···O2 | 0.95 | 2.28 | 2.8281 (14) | 116 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Φ1, Φ2, and Φ3 are torsion angles defined as C5—C4—C1—C2, C4—C1—C2—C3, and C2—C3—C10—C11, respectively. |
Chalcone | Φ1 | Φ2 | Φ3 |
m'PMIpCH3 | -173.11 (11) | -171.62 (11) | 165.47 (13) |
m'AApCH3 | -162.18 (15) | 165.39 (15) | 179.24 (18) |
m'AApCH3 has no R-ring. |
Chalcone | 1-Ring/3-Ring twist | 1-Ring/3-Ring fold | 1-Ring/R-Ring twist | 1-Ring/R-Ring fold |
m'PMIpCH3 | 178.52 (6) | 154.6 (8) | 140.16 (6) | 25.27 (16) |
m'AApCH3 | 0.89 (4) | 4.21 (4) | n.a. | n.a. |
Distances to the 1-Ring, 3-Ring, and R-Ring reflect distances to the centroids of those rings. The sums of the van der Waals (VDW) radii (Å) for hydrogen plus carbon, nitrogen, or oxygen are 2.9, 2.75, and 2.72, respectively, while the sum for carbon plus carbon is 3.4 and the sum for hydrogen plus hydrogen is 2.4; distances greater than the sum of the VDW radii are italicized. The symmetry codes apply to those molecules interacting with the asymmetric unit. Symmetry codes m'PMIpCH3: (i) -x+1, -y+2, -z+1; (ii) -x+1, y, -z+3/2; (iii) x, y-1, z. Symmetry codes for m'AApCH3: (i) -x+1, -y+2, -z+1; (ii) x+1/2, -y+1/2, z+1/2; (iii) x+1/2, -y+3/2, z+1/2; (iv) -x+1, y, -z+1/2. Standard uncertainties are listed in parentheses. |
m'PMIpCH3 | Distance | m'AApCH3 | Distance |
C21—H21···O1i | 2.6701 (10) | N1—HN1···O1i | 2.164 (16) |
C15—H15···C15ii | 2.8394 (16) | C3—H3···H17Bi | 2.28041 (4) |
C15···C15ii | 3.310 (3) | O2···H18A—C18ii | 2.400 (2) |
1-Ring···R-Ringiii | 4.7168 (10) | O2···H11—C11iii | 2.6087 (8) |
C7–H7···C18iii | 2.8745 (16) | 1-Ring···3-Ringiv | 4.7134 (7) |
C9—H9···C14iv | 2.9584 (11) |