In the title compound, the crystal packing features C—H⋯Cl hydrogen bonds, which form R22(12) graph-set motifs.
Keywords: piperidine derivative, intermolecular hydrogen bonds, Hirshfeld surface analysis, crystal structure
Abstract
In the crystal structure of the title compound, C22H24ClNO2, the piperidine ring adopts a boat conformation. Intra- and intermolecular C—H⋯Cl hydrogen bonds are observed. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, revealing that H⋯H interactions contribute most to the crystal packing (56.1%).
1. Chemical context
Piperidin-4-one derivatives represent a significant class of heterocyclic compounds widely documented for their versatility in the field of medicinal chemistry. The piperidin-4-one scaffold serves as a valuable synthetic intermediate and as a promising pharmacophore showing diverse biological activities (Sahu et al., 2013 ▸). Among piperidin-4-one derivatives, 3-alkyl-2,6-diarylpiperidin-4-one derivatives have been extensively investigated, particularly with respect to their synthesis, stereochemistry, and diverse biological activities. 3-Alkyl-2,6-diarylpiperidone derivatives predominantly adopt a chair conformation with an equatorial orientation of the alkyl and phenyl substituents (Pandiarajan et al., 1991 ▸). The introduction of groups such as –NO, –CHO, –COCH3, and N—COCH2Cl onto the ring nitrogen atom of a 2,6-diarylpiperidin-4-one moiety significantly alter the ring conformation and the orientation of its substituents. Delocalization of the nitrogen lone pair into the –COR π-system imparts partial double-bond character to the —N—CO linkage, thereby restricting its rotation. The steric interaction between the N—CO group and the neighbouring equatorial substituent causes molecular strain, which is relieved by adopting a chair form with an axial orientation of the phenyl substituents or a boat form with one phenyl substituent in the flagpole position. The effects of such substitutions on the geometry of the piperidin-4-one nucleus have been extensively reported. Structural variations such as N-benzoyl (Krishnapillay et al., 2000 ▸), N-nitroso (Ravindran et al., 1991 ▸), N-formyl (Pandiarajan et al., 1997 ▸), N-chloroacetyl (Aridoss et al., 2007a ▸,b ▸; Divyabharathi et al., 2024 ▸) and N-thiocyanatoacetyl (Karthiga et al., 2024 ▸, 2025 ▸) derivatives have all been studied. Furthermore, investigations into the DNA-binding properties of N-acetyl analogues (Mohanraj & Ponnuswamy, 2018 ▸) and their antibacterial activities (Aridoss et al., 2008 ▸) have also been reported. In the present work, crystal structure and Hirshfeld surface analysis of 1-(2-chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one, are reported.
2. Structural commentary
The molecular structure is presented in Fig. 1 ▸. The compound is chiral due to the presence of stereogenic centres. Although the molecular structure depicted in Fig. 1 ▸ shows the 2R,3S,6S enantiomer, the crystal contains a racemic mixture of enantiomers. The O1—C3 [1.207 (2) Å] and O2—C6 [1.221 (2) Å] bond lengths confirm the double-bond character. The sum of the angles around atom N1 (357.1°) indicates that nitrogen adopts an almost trigonal–planar geometry. Conjugation between the carbonyl group and the adjacent C—C bond, combined with steric hindrance from the chloromethyl substituent, restricts free rotation about the C6—C7 bond. This limited rotational freedom results in distinct preferred conformations, which is reflected in the observed torsion angles O2—C6—C7—Cl1 [100.5 (2)°] and N1—C6—C7—Cl1 [−80.4 (2)°]. The piperidine ring adopts a boat conformation; the puckering parameters (Cremer & Pople, 1975 ▸) are: q2 = 0.677 (2) Å, q3 = −0.060 (2) Å, QT = 0.680 (2) Å and φ = 107.4 (2)°. Atoms C2 and C5 in the piperidine ring (N1/C1–C5) deviate by −0.528 (2) and −0.604 (2) Å, respectively, from the least-squares plane through the remaining four atoms. The methylphenyl rings C8–C13 and C15–C21 are planar, with their attached methyl atoms C14 and C22 deviate by −0.024 (3) and 0.003 (3) Å, respectively, from their ring planes. These methylphenyl rings are oriented with a dihedral angle of 51.7 (1)° with respect to each other. A weak intramolecular contact (Table 1 ▸) between a methine H atom and the Cl atom attached to the 2-chloroacetaldehyde moiety (C6/O2/C7/Cl1) leads to the stabilization of the molecular conformation. This C5—H5⋯Cl1 interaction forms an S(6) ring motif (Bernstein et al., 1995 ▸), as shown in Fig. 1 ▸.
Figure 1.
Molecular structure showing the atom-labelling scheme and the intramolecular hydrogen bond (dashed line). Ellipsoids are drawn at the 30% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
Cg is the centroid of the C8–C13 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C5—H5⋯Cl1 | 0.98 | 2.61 | 3.342 (2) | 132 |
| C1—H1⋯Cl1i | 0.98 | 2.79 | 3.674 (2) | 151 |
| C7—H7A⋯Cgii | 0.97 | 2.85 | 3.575 (2) | 133 |
Symmetry codes: (i) 
; (ii) 
.
3. Supramolecular features
In the crystal, molecules associate pairwise via C1—H1⋯Cl1i hydrogen bonds (Table 1 ▸) into inversion dimers with an 
(12) graph-set motif (Etter et al., 1990 ▸), as shown in Fig. 2 ▸. Moreover, molecules are further linked into an (14) graph-set motif by C—H⋯π interactions, C7—H7A⋯Cg, where Cg is the centroid of the symmetry-related C8–C13 benzene ring at (2 − x, 2 − y, 1 − z) (Table 1 ▸).
Figure 2.
Centrosymmetric dimer through C—H⋯Cl hydrogen bonds [Symmetry code: (a) −x + 1, −y, −z + 1].
4. Hirshfeld surface analysis
The intermolecular interactions were quantified by a Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ▸) using CrystalExplorer (Spackman et al., 2021 ▸). The HS mapped over dnorm is illustrated in Fig. 3 ▸. where no red spot occurs. This represents the non-availability of potential hydrogen bonds in this crystal. The associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) provide quantitative information about the non-covalent interactions in the crystal packing in terms of the percentage contribution of the interatomic contacts (Spackman & McKinnon, 2002 ▸). The overall two-dimensional fingerprint plot is shown in Fig. 4 ▸a (top left). The HS analysis reveals that H⋯H and H⋯O/O⋯H contacts are the main contributors to the crystal packing followed by H⋯C/C⋯H, H⋯Cl/Cl⋯H, Cl⋯C/C⋯Cl, C⋯C and Cl⋯O/O⋯Cl contacts; see Fig. 4 ▸b–h.
Figure 3.
Hirshfeld surface mapped over dnorm.
Figure 4.
Two-dimensional fingerprint plots showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e)H⋯Cl/Cl⋯H, (f) Cl⋯C/C⋯Cl, (g) C⋯C and (h) Cl⋯O/O⋯Cl interactions. The di and de values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.
5. Synthesis and crystallization
The compound has been previously reported, and all characterization data are consistent with those described by Aridoss et al., 2007a ▸,b ▸. The compound was synthesized by mixing 3-methyl-2,6-di-p-tolylpiperidin-4-one (0.75 g, 2.5 mmol) and chloroacetyl chloride (1.0 mL, 10 mmol). The mixture was stirred in anhydrous benzene (50 mL) at room temperature. Then, triethylamine (1.4 mL, 10 mmol) was added as a base to initiate the reaction. The reaction mixture was maintained at room temperature for 6 h. Upon completion, the precipitated triethylammonium chloride salt was removed by filtration. The resulting organic layer was washed thoroughly with water then dried over anhydrous Na2SO4. The solvent was removed and the crude product was recrystallized from a mixture of petroleum ether and ethyl acetate (9:1, v/v) to afford the product as colourless crystals.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C22H24ClNO2 |
| M r | 369.87 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 298 |
| a, b, c (Å) | 8.7654 (5), 11.3919 (6), 11.6090 (7) |
| α, β, γ (°) | 110.594 (2), 102.709 (2), 107.595 (2) |
| V (Å3) | 962.71 (10) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.21 |
| Crystal size (mm) | 0.35 × 0.23 × 0.19 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.711, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 24328, 5355, 3183 |
| R int | 0.043 |
| (sin θ/λ)max (Å−1) | 0.706 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.135, 1.03 |
| No. of reflections | 5355 |
| No. of parameters | 238 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.18, −0.27 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989026000083/tx2106sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000083/tx2106Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026000083/tx2106sup3.txt
CCDC reference: 2184416
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Single Crystal XRD Facility at the Department of Chemistry, Annamalai University,Tamil Nadu, India, for providing the instrumentation and support necessary for this study.
supplementary crystallographic information
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Crystal data
| C22H24ClNO2 | Z = 2 |
| Mr = 369.87 | F(000) = 392 |
| Triclinic, P1 | Dx = 1.276 Mg m−3 |
| a = 8.7654 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.3919 (6) Å | Cell parameters from 6744 reflections |
| c = 11.6090 (7) Å | θ = 2.6–28.8° |
| α = 110.594 (2)° | µ = 0.21 mm−1 |
| β = 102.709 (2)° | T = 298 K |
| γ = 107.595 (2)° | Block, colourless |
| V = 962.71 (10) Å3 | 0.35 × 0.23 × 0.19 mm |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Data collection
| Bruker APEXII CCD diffractometer | 3183 reflections with I > 2σ(I) |
| Radiation source: i-mu-s microfocus source | Rint = 0.043 |
| φ and ω scans | θmax = 30.1°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→12 |
| Tmin = 0.711, Tmax = 0.746 | k = −15→16 |
| 24328 measured reflections | l = −15→16 |
| 5355 independent reflections |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
| wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2977P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 5355 reflections | Δρmax = 0.18 e Å−3 |
| 238 parameters | Δρmin = −0.27 e Å−3 |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. 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. |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.25775 (8) | −0.21845 (5) | 0.47830 (6) | 0.0760 (2) | |
| O1 | 0.85771 (18) | 0.29415 (17) | 0.90454 (19) | 0.0905 (6) | |
| O2 | 0.20241 (19) | 0.06629 (14) | 0.46708 (13) | 0.0676 (4) | |
| N1 | 0.34459 (17) | 0.11084 (13) | 0.67584 (13) | 0.0436 (3) | |
| C1 | 0.4496 (2) | 0.25412 (16) | 0.70160 (16) | 0.0430 (4) | |
| H1 | 0.493746 | 0.246576 | 0.629971 | 0.052* | |
| C2 | 0.6072 (2) | 0.33108 (17) | 0.83254 (17) | 0.0467 (4) | |
| H2 | 0.563298 | 0.350761 | 0.904614 | 0.056* | |
| C3 | 0.7039 (2) | 0.2449 (2) | 0.84836 (19) | 0.0544 (4) | |
| C4 | 0.5966 (2) | 0.09311 (18) | 0.79297 (19) | 0.0523 (4) | |
| H4A | 0.639400 | 0.060054 | 0.854009 | 0.063* | |
| H4B | 0.608122 | 0.044809 | 0.710194 | 0.063* | |
| C5 | 0.4065 (2) | 0.05969 (17) | 0.76895 (16) | 0.0459 (4) | |
| H5 | 0.345337 | −0.041045 | 0.722924 | 0.055* | |
| C6 | 0.2292 (2) | 0.02538 (18) | 0.55034 (17) | 0.0498 (4) | |
| C7 | 0.1282 (2) | −0.12542 (18) | 0.5127 (2) | 0.0589 (5) | |
| H7A | 0.025083 | −0.164551 | 0.435285 | 0.071* | |
| H7B | 0.093917 | −0.133089 | 0.584595 | 0.071* | |
| C8 | 0.3460 (2) | 0.33884 (16) | 0.69974 (16) | 0.0436 (4) | |
| C9 | 0.2647 (2) | 0.36976 (18) | 0.78849 (18) | 0.0501 (4) | |
| H9 | 0.266432 | 0.332410 | 0.848017 | 0.060* | |
| C10 | 0.1809 (2) | 0.45532 (19) | 0.79026 (19) | 0.0551 (5) | |
| H10 | 0.125999 | 0.473644 | 0.850156 | 0.066* | |
| C11 | 0.1777 (2) | 0.51415 (19) | 0.70398 (19) | 0.0577 (5) | |
| C12 | 0.2585 (3) | 0.4826 (2) | 0.6152 (2) | 0.0632 (5) | |
| H12 | 0.257599 | 0.520543 | 0.556190 | 0.076* | |
| C13 | 0.3407 (3) | 0.39610 (19) | 0.61200 (17) | 0.0552 (5) | |
| H13 | 0.392961 | 0.375967 | 0.550488 | 0.066* | |
| C14 | 0.0891 (3) | 0.6093 (2) | 0.7089 (3) | 0.0801 (7) | |
| H14A | 0.090380 | 0.653225 | 0.796661 | 0.120* | |
| H14B | −0.027693 | 0.557154 | 0.647625 | 0.120* | |
| H14C | 0.148117 | 0.678073 | 0.685548 | 0.120* | |
| C15 | 0.7241 (3) | 0.4697 (2) | 0.8473 (2) | 0.0629 (5) | |
| H15A | 0.665406 | 0.529360 | 0.857365 | 0.094* | |
| H15B | 0.753294 | 0.455989 | 0.769991 | 0.094* | |
| H15C | 0.827119 | 0.511073 | 0.923769 | 0.094* | |
| C16 | 0.3612 (2) | 0.10762 (17) | 0.89173 (17) | 0.0459 (4) | |
| C17 | 0.4756 (3) | 0.15250 (19) | 1.01738 (18) | 0.0566 (5) | |
| H17 | 0.586631 | 0.158729 | 1.028921 | 0.068* | |
| C18 | 0.4274 (3) | 0.1882 (2) | 1.12598 (19) | 0.0623 (5) | |
| H18 | 0.507013 | 0.218030 | 1.209176 | 0.075* | |
| C19 | 0.2642 (3) | 0.18084 (19) | 1.1142 (2) | 0.0605 (5) | |
| C20 | 0.1502 (3) | 0.1367 (2) | 0.9891 (2) | 0.0628 (5) | |
| H20 | 0.039547 | 0.131290 | 0.977987 | 0.075* | |
| C21 | 0.1972 (2) | 0.1003 (2) | 0.87960 (19) | 0.0546 (5) | |
| H21 | 0.117321 | 0.070404 | 0.796475 | 0.066* | |
| C22 | 0.2150 (4) | 0.2203 (3) | 1.2342 (2) | 0.0888 (8) | |
| H22A | 0.095320 | 0.202382 | 1.207207 | 0.133* | |
| H22B | 0.282704 | 0.316607 | 1.292575 | 0.133* | |
| H22C | 0.235683 | 0.167058 | 1.279197 | 0.133* |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0787 (4) | 0.0539 (3) | 0.0795 (4) | 0.0288 (3) | 0.0323 (3) | 0.0103 (3) |
| O1 | 0.0434 (8) | 0.0746 (10) | 0.1260 (15) | 0.0156 (8) | 0.0014 (9) | 0.0413 (10) |
| O2 | 0.0794 (10) | 0.0584 (8) | 0.0419 (7) | 0.0190 (7) | 0.0066 (7) | 0.0156 (6) |
| N1 | 0.0441 (8) | 0.0359 (7) | 0.0393 (7) | 0.0099 (6) | 0.0108 (6) | 0.0130 (6) |
| C1 | 0.0439 (9) | 0.0388 (8) | 0.0402 (9) | 0.0113 (7) | 0.0144 (7) | 0.0168 (7) |
| C2 | 0.0419 (9) | 0.0395 (9) | 0.0453 (9) | 0.0094 (7) | 0.0092 (7) | 0.0154 (7) |
| C3 | 0.0427 (10) | 0.0543 (11) | 0.0571 (11) | 0.0145 (9) | 0.0129 (8) | 0.0234 (9) |
| C4 | 0.0499 (10) | 0.0485 (10) | 0.0582 (11) | 0.0215 (8) | 0.0182 (9) | 0.0237 (9) |
| C5 | 0.0464 (9) | 0.0366 (8) | 0.0468 (9) | 0.0126 (7) | 0.0129 (8) | 0.0170 (7) |
| C6 | 0.0468 (10) | 0.0432 (9) | 0.0425 (10) | 0.0138 (8) | 0.0104 (8) | 0.0092 (8) |
| C7 | 0.0478 (10) | 0.0428 (10) | 0.0591 (11) | 0.0111 (8) | 0.0088 (9) | 0.0073 (9) |
| C8 | 0.0431 (9) | 0.0375 (8) | 0.0372 (8) | 0.0094 (7) | 0.0073 (7) | 0.0138 (7) |
| C9 | 0.0524 (10) | 0.0475 (10) | 0.0484 (10) | 0.0181 (8) | 0.0160 (8) | 0.0231 (8) |
| C10 | 0.0506 (10) | 0.0515 (10) | 0.0549 (11) | 0.0194 (9) | 0.0157 (9) | 0.0189 (9) |
| C11 | 0.0486 (10) | 0.0469 (10) | 0.0573 (12) | 0.0149 (9) | 0.0006 (9) | 0.0175 (9) |
| C12 | 0.0713 (13) | 0.0591 (12) | 0.0531 (11) | 0.0229 (11) | 0.0084 (10) | 0.0308 (10) |
| C13 | 0.0650 (12) | 0.0543 (11) | 0.0415 (10) | 0.0214 (10) | 0.0146 (9) | 0.0224 (8) |
| C14 | 0.0723 (15) | 0.0693 (14) | 0.0925 (17) | 0.0371 (12) | 0.0105 (13) | 0.0352 (13) |
| C15 | 0.0533 (11) | 0.0474 (10) | 0.0654 (13) | 0.0044 (9) | 0.0095 (9) | 0.0230 (10) |
| C16 | 0.0494 (10) | 0.0372 (8) | 0.0466 (10) | 0.0124 (7) | 0.0155 (8) | 0.0199 (7) |
| C17 | 0.0559 (11) | 0.0534 (11) | 0.0502 (11) | 0.0165 (9) | 0.0132 (9) | 0.0215 (9) |
| C18 | 0.0768 (14) | 0.0496 (11) | 0.0446 (10) | 0.0157 (10) | 0.0128 (10) | 0.0187 (9) |
| C19 | 0.0852 (15) | 0.0444 (10) | 0.0581 (12) | 0.0258 (10) | 0.0336 (11) | 0.0264 (9) |
| C20 | 0.0664 (13) | 0.0701 (13) | 0.0721 (14) | 0.0326 (11) | 0.0370 (11) | 0.0427 (11) |
| C21 | 0.0539 (11) | 0.0593 (11) | 0.0542 (11) | 0.0202 (9) | 0.0202 (9) | 0.0319 (9) |
| C22 | 0.133 (2) | 0.0797 (16) | 0.0738 (16) | 0.0489 (17) | 0.0600 (16) | 0.0382 (13) |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Geometric parameters (Å, º)
| Cl1—C7 | 1.789 (2) | C10—H10 | 0.9300 |
| O1—C3 | 1.207 (2) | C11—C12 | 1.381 (3) |
| O2—C6 | 1.221 (2) | C11—C14 | 1.505 (3) |
| N1—C6 | 1.361 (2) | C12—C13 | 1.380 (3) |
| N1—C5 | 1.476 (2) | C12—H12 | 0.9300 |
| N1—C1 | 1.493 (2) | C13—H13 | 0.9300 |
| C1—C8 | 1.514 (2) | C14—H14A | 0.9600 |
| C1—C2 | 1.547 (2) | C14—H14B | 0.9600 |
| C1—H1 | 0.9800 | C14—H14C | 0.9600 |
| C2—C3 | 1.509 (3) | C15—H15A | 0.9600 |
| C2—C15 | 1.526 (2) | C15—H15B | 0.9600 |
| C2—H2 | 0.9800 | C15—H15C | 0.9600 |
| C3—C4 | 1.502 (3) | C16—C17 | 1.384 (2) |
| C4—C5 | 1.528 (2) | C16—C21 | 1.387 (3) |
| C4—H4A | 0.9700 | C17—C18 | 1.382 (3) |
| C4—H4B | 0.9700 | C17—H17 | 0.9300 |
| C5—C16 | 1.523 (2) | C18—C19 | 1.380 (3) |
| C5—H5 | 0.9800 | C18—H18 | 0.9300 |
| C6—C7 | 1.519 (3) | C19—C20 | 1.381 (3) |
| C7—H7A | 0.9700 | C19—C22 | 1.506 (3) |
| C7—H7B | 0.9700 | C20—C21 | 1.385 (3) |
| C8—C9 | 1.383 (2) | C20—H20 | 0.9300 |
| C8—C13 | 1.389 (2) | C21—H21 | 0.9300 |
| C9—C10 | 1.384 (3) | C22—H22A | 0.9600 |
| C9—H9 | 0.9300 | C22—H22B | 0.9600 |
| C10—C11 | 1.387 (3) | C22—H22C | 0.9600 |
| C6—N1—C5 | 122.82 (14) | C11—C10—H10 | 119.5 |
| C6—N1—C1 | 115.84 (14) | C12—C11—C10 | 117.69 (18) |
| C5—N1—C1 | 118.41 (13) | C12—C11—C14 | 122.0 (2) |
| N1—C1—C8 | 113.14 (13) | C10—C11—C14 | 120.4 (2) |
| N1—C1—C2 | 112.07 (13) | C13—C12—C11 | 121.62 (18) |
| C8—C1—C2 | 110.05 (13) | C13—C12—H12 | 119.2 |
| N1—C1—H1 | 107.1 | C11—C12—H12 | 119.2 |
| C8—C1—H1 | 107.1 | C12—C13—C8 | 120.64 (18) |
| C2—C1—H1 | 107.1 | C12—C13—H13 | 119.7 |
| C3—C2—C15 | 112.14 (15) | C8—C13—H13 | 119.7 |
| C3—C2—C1 | 112.78 (14) | C11—C14—H14A | 109.5 |
| C15—C2—C1 | 110.77 (14) | C11—C14—H14B | 109.5 |
| C3—C2—H2 | 106.9 | H14A—C14—H14B | 109.5 |
| C15—C2—H2 | 106.9 | C11—C14—H14C | 109.5 |
| C1—C2—H2 | 106.9 | H14A—C14—H14C | 109.5 |
| O1—C3—C4 | 121.39 (18) | H14B—C14—H14C | 109.5 |
| O1—C3—C2 | 122.60 (18) | C2—C15—H15A | 109.5 |
| C4—C3—C2 | 115.99 (15) | C2—C15—H15B | 109.5 |
| C3—C4—C5 | 112.45 (15) | H15A—C15—H15B | 109.5 |
| C3—C4—H4A | 109.1 | C2—C15—H15C | 109.5 |
| C5—C4—H4A | 109.1 | H15A—C15—H15C | 109.5 |
| C3—C4—H4B | 109.1 | H15B—C15—H15C | 109.5 |
| C5—C4—H4B | 109.1 | C17—C16—C21 | 117.32 (17) |
| H4A—C4—H4B | 107.8 | C17—C16—C5 | 122.49 (16) |
| N1—C5—C16 | 112.38 (14) | C21—C16—C5 | 120.10 (15) |
| N1—C5—C4 | 108.01 (14) | C18—C17—C16 | 121.07 (19) |
| C16—C5—C4 | 116.21 (14) | C18—C17—H17 | 119.5 |
| N1—C5—H5 | 106.5 | C16—C17—H17 | 119.5 |
| C16—C5—H5 | 106.5 | C19—C18—C17 | 121.76 (19) |
| C4—C5—H5 | 106.5 | C19—C18—H18 | 119.1 |
| O2—C6—N1 | 122.11 (16) | C17—C18—H18 | 119.1 |
| O2—C6—C7 | 118.71 (16) | C18—C19—C20 | 117.24 (18) |
| N1—C6—C7 | 119.17 (17) | C18—C19—C22 | 120.7 (2) |
| C6—C7—Cl1 | 109.87 (13) | C20—C19—C22 | 122.1 (2) |
| C6—C7—H7A | 109.7 | C19—C20—C21 | 121.4 (2) |
| Cl1—C7—H7A | 109.7 | C19—C20—H20 | 119.3 |
| C6—C7—H7B | 109.7 | C21—C20—H20 | 119.3 |
| Cl1—C7—H7B | 109.7 | C20—C21—C16 | 121.20 (18) |
| H7A—C7—H7B | 108.2 | C20—C21—H21 | 119.4 |
| C9—C8—C13 | 117.95 (16) | C16—C21—H21 | 119.4 |
| C9—C8—C1 | 122.47 (15) | C19—C22—H22A | 109.5 |
| C13—C8—C1 | 119.44 (16) | C19—C22—H22B | 109.5 |
| C8—C9—C10 | 121.14 (17) | H22A—C22—H22B | 109.5 |
| C8—C9—H9 | 119.4 | C19—C22—H22C | 109.5 |
| C10—C9—H9 | 119.4 | H22A—C22—H22C | 109.5 |
| C9—C10—C11 | 120.95 (19) | H22B—C22—H22C | 109.5 |
| C9—C10—H10 | 119.5 | ||
| C6—N1—C1—C8 | 70.04 (18) | C2—C1—C8—C9 | −63.9 (2) |
| C5—N1—C1—C8 | −128.78 (15) | N1—C1—C8—C13 | −122.15 (16) |
| C6—N1—C1—C2 | −164.83 (15) | C2—C1—C8—C13 | 111.63 (17) |
| C5—N1—C1—C2 | −3.6 (2) | C13—C8—C9—C10 | −0.1 (3) |
| N1—C1—C2—C3 | 46.1 (2) | C1—C8—C9—C10 | 175.48 (16) |
| C8—C1—C2—C3 | 172.88 (14) | C8—C9—C10—C11 | −0.8 (3) |
| N1—C1—C2—C15 | 172.67 (15) | C9—C10—C11—C12 | 1.0 (3) |
| C8—C1—C2—C15 | −60.51 (19) | C9—C10—C11—C14 | −178.77 (18) |
| C15—C2—C3—O1 | 21.0 (3) | C10—C11—C12—C13 | −0.3 (3) |
| C1—C2—C3—O1 | 146.9 (2) | C14—C11—C12—C13 | 179.49 (19) |
| C15—C2—C3—C4 | −160.61 (16) | C11—C12—C13—C8 | −0.7 (3) |
| C1—C2—C3—C4 | −34.7 (2) | C9—C8—C13—C12 | 0.9 (3) |
| O1—C3—C4—C5 | 160.7 (2) | C1—C8—C13—C12 | −174.90 (17) |
| C2—C3—C4—C5 | −17.7 (2) | N1—C5—C16—C17 | −138.29 (17) |
| C6—N1—C5—C16 | −118.60 (17) | C4—C5—C16—C17 | −13.2 (2) |
| C1—N1—C5—C16 | 81.61 (17) | N1—C5—C16—C21 | 45.3 (2) |
| C6—N1—C5—C4 | 111.89 (17) | C4—C5—C16—C21 | 170.40 (16) |
| C1—N1—C5—C4 | −47.90 (18) | C21—C16—C17—C18 | 0.1 (3) |
| C3—C4—C5—N1 | 58.85 (19) | C5—C16—C17—C18 | −176.44 (16) |
| C3—C4—C5—C16 | −68.5 (2) | C16—C17—C18—C19 | 0.0 (3) |
| C5—N1—C6—O2 | −166.44 (17) | C17—C18—C19—C20 | −0.3 (3) |
| C1—N1—C6—O2 | −6.2 (3) | C17—C18—C19—C22 | 179.97 (19) |
| C5—N1—C6—C7 | 14.5 (2) | C18—C19—C20—C21 | 0.5 (3) |
| C1—N1—C6—C7 | 174.76 (15) | C22—C19—C20—C21 | −179.78 (19) |
| O2—C6—C7—Cl1 | 100.48 (19) | C19—C20—C21—C16 | −0.4 (3) |
| N1—C6—C7—Cl1 | −80.42 (19) | C17—C16—C21—C20 | 0.1 (3) |
| N1—C1—C8—C9 | 62.3 (2) | C5—C16—C21—C20 | 176.72 (16) |
1-(2-Chloroacetyl)-3-methyl-2,6-bis(4-methylphenyl)piperidin-4-one. Hydrogen-bond geometry (Å, º)
Cg is the centroid of the C8–C13 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···Cl1 | 0.98 | 2.61 | 3.342 (2) | 132 |
| C1—H1···Cl1i | 0.98 | 2.79 | 3.674 (2) | 151 |
| C7—H7A···Cgii | 0.97 | 2.85 | 3.575 (2) | 133 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+2, −z+1.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989026000083/tx2106sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000083/tx2106Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026000083/tx2106sup3.txt
CCDC reference: 2184416
Additional supporting information: crystallographic information; 3D view; checkCIF report