An investigation is reported of the synthesis and crystal structure of 4-benzyl-4-pentylmorpholin-4-ium chloride
Keywords: crystal structure, molecular structure, N-pentyl morpholine, benzyl chloride, quaternary morpholine halide
Abstract
The reaction of N-pentylmorpholine with benzyl chloride resulted in the title compound, C16H26ClNO, which crystallizes in the orthorhombic space group Pna21 with Z = 4. In the crystal, the chloride ions are surrounded by four cations, forming layers.
1. Chemical context
Morpholine is a multipurpose chemical that is used as a solvent for resins, dyes and waxes. One of its most important uses is as a chemical intermediate in the preparation of pesticides (Muruganandam et al., 2009 ▸). A number of morpholine derivatives have been described as analgesics and local anesthetics. The morpholinomethyl derivative of pyrizinamide (morphozinamide) has been found to be more effective in the treatment of tuberculosis than pyrizinamide (Sedavkina et al., 1984 ▸). Quaternary morpholine halides were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922. (Morandini et al., 2021 ▸). Additionally, most drugs containing a morpholine moiety in their structure have been found to exhibit significant biological properties (Basavaraja et al., 2010 ▸). Quaternary morpholine halides are valuable precursors for the preparation of ionic liquids (ILs) by ion metathesis (Kim et al., 2005 ▸). The excellent conductivity, broad electrochemical window, thermal stability, and low volatility of ILs have made them promising media for electrochemical processes (Zein El Abedin et al., 2004 ▸, 2005 ▸). In particular, ILs based on the morpholinium cation are favored because of their low cost, easy synthesis, and electrochemical stability (Kim et al., 2006 ▸). We report here a new example structure of this class.
2. Structural commentary
The title compound crystallizes in the orthorhombic space group Pna21 with Z = 4. The asymmetric unit consists of a 4-benzyl-4-pentylmorpholin-4-ium cation with a quaternary nitrogen atom and the chloride counter-anion, which ensures neutrality (Fig. 1 ▸). The average C—N bond length of 1.521 Å and C—N—C angle of 109° are consistent with the geometry of a charged quaternary nitrogen atom found in different structures (Rousselin & Clavel, 2024 ▸). In the cation, the morpholinium ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975 ▸) of the ring Q = 0.5711 (18) Å, θ = 4.26 (18)°, φ = 29 (2)°. Weak intramolecular C—H ⋯Cl hydrogen bonds help to consolidate the conformation of the molecule (Table 1 ▸). The pentyl group carbon atoms lie in a plane with an r.m.s. deviation of 0.0252 Å.
Figure 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 is the centroid of the benzene ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C2—H2B⋯Cl1i | 0.97 | 2.78 | 3.708 (2) | 160 |
| C3—H3B⋯Cl1ii | 0.97 | 2.78 | 3.645 (2) | 149 |
| C6—H6B⋯Cl1 | 0.97 | 2.77 | 3.477 (2) | 130 |
| C12—H12B⋯Cl1ii | 0.97 | 2.75 | 3.639 (2) | 153 |
| C15—H15⋯Cg1iii | 0.93 | 3.28 | 4.104 (3) | 149 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
3. Supramolecular features
The crystal packing is shown in Fig. 2 ▸, where four cations, accompanied by counter-ions, are arranged head-to-tail in the unit cell. An examination of the distribution of the positively charged nitrogen atoms in the morpholinium cations and the chloride counter-ions shows that the crystal forms ion layers parallel to the bc plane, which corresponds to the planar surface of the monocrystal (Fig. 3 ▸). Within these layers, each nitrogen atom forms short contacts with four chloride ions at distances of 3.938 (2), 4.657 (2), 4.892 (2), and 4.988 (2) Å. The chloride ions are separated by a distance of 6.3470 (4) Å, forming a two-dimensional structure typical of salts with a cyclobutane-like puckering conformation. Each chloride ion is surrounded by methylene groups, which form weak C—H⋯Cl hydrogen bonds (Table 1 ▸). The arrangement and geometry of the nitrogen atoms are similar, with a nitrogen–nitrogen distance of 6.673 (1) Å (Fig. 4 ▸). These layers are packed through the partial intercalation of alkyl and phenyl groups along the a axis, forming Car—H⋯π interactions (Table 1 ▸).
Figure 2.
The packing of the title compound.
Figure 3.
Screenshot from the face-indexing procedure (showing the unit-cell axes).
Figure 4.
Distribution of positively charged nitrogen atoms and chloride counter-ions in a layer. Interatomic distances are given in Å.
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.46 of November 2024; Groom et al., 2016 ▸) for structures containing a morpholine fragment with three bonded nitrogen atom returned 2745 hits. A search for structures containing a morpholin-4-ium fragment returned 188 hits, while a search for the morpholin-4-ium fragment with a benzyl substituent produced 10 matches. Homologous structures with methyl and ethyl substituents are MOKJOM (Bian, 2009a ▸) and DOKYAE (Bian, 2009b ▸). The C—N bond length in a neutral morpholine fragment is approximately 1.46–1.48 Å (Groom et al., 2016 ▸; Mutalliev et al., 2022 ▸) while the C—N bond in a morpholin-4-ium structure, as mentioned above, measures around 1.52 Å.
5. Synthesis and crystallization
N-pentyl morpholine, C9H19NO. To a 50 ml round-bottom flask, 4.95 g (0.06 mol) of morpholine were added. After adding 0.6 mol of ethanol as the solvent, 0.06 mol of potassium carbonate (K2CO3) and then 7.50 ml (0.06 mol) of pentyl bromide were added. The reaction mixture was heated under reflux with magnetic stirring for 1–9 h (monitored by TLC). Afterward, the solvent was evaporated. The remaining potassium carbonate in the solution was dissolved in water, and the reaction product was extracted with chloroform (CHCl3). After the chloroform had evaporated, the residue was dried under vacuum. Yield 6.5 g (72.0%).
1 H-NMR (600 MHz, CDCl3, δ, ppm J/Hz): 0.85 (3H, t, J = 7.2, H-11), 1.26 (4H, m, H-9,10), 1.44 (2H, kd, J = 7.4, 2.1, H-8), 2.27 (2H, dt, J = 7.9, 2.4, H-7), 2.39 (4H, s, H-2,6), 3.68 (4H, s, H-3,5).
13C NMR (150 MHz, CDCl3, δ, ppm): 14.09 (C-11), 22.41 (C-10), 26.31 (C-8), 29.89 (C-9), 53.62 (C-2,6), 59.29 (C-7), 66,93 (C-3,5).
IR spectrum (KBr, νmax, cm−1): 2957, 2931, 2856, 2807, 1708, 1454, 1358, 1271, 1118, 1071-1757, 1034, 1004, 914, 864, 796, 628.
4-Benzyl-4-pentylmorpholin-4-ium chloride, C16H26ClNO. To a 50 ml round-bottom flask, 2 g (0.013 mol) of N-pentyl morpholine were added. After adding 5.4 ml (0.104 mol) of acetonitrile as the solvent, 0.013 mol of potassium carbonate (K2CO3) were added, followed by benzyl chloride in a 1:1 ratio, i.e., 0.013 mol. The reaction mixture was heated under reflux with magnetic stirring for 5 h (monitored by TLC). Then the solvent was evaporated, the remaining potassium carbonate was dissolved in water, and the reaction product was extracted with chloroform (CHCl3). After the chloroform had evaporated, the product was dried under vacuum. The obtained product was purified using column chromatography. Yield 3.16 g (94.0%), m.p. 467–469 K. Single crystals were obtained by slow evaporation of an acetone solution.
1 H-NMR (600 MHz, CDCl3, δ, ppm J/Hz): 0.87 (3H, t, J = 6.19, H-11), 1.33 (4H, m, H-9,10), 1.80 (2H, m, H-8), 3.40 (2H, dd, J = 9.63, 2.38, H-7), 3.58 (4H, m, H-1,5), 3.76 (2H, t, J = 10.41 H-12), 3.95 (2H, m, H-2), 4.07 (2H, d, J = 13.94 H-4), 7.40 (3H, m, H-16,17,15), 7.58 (2H, d, J = 4.95 H-18,14).
13C NMR (150 MHz, CDCl3, δ, ppm): 13.94 (C-18), 21.84 (C-17), 22.31 (C-15), 28.42 (C-16), 56.33 (C-2,4), 56.98 (C-7), 60,62 (C-1,5), 64,85 (C-8), 126.77 (C-9), 129.42 (C-11,13), 130.86 (C-12), 133.40 (C-10,14).
IR spectrum (KBr, νmax, cm−1): 2976, 2951, 2873, 1495, 1458, 1393, 1216, 1121, 1050, 1019, 991, 946, 932, 912, 886, 860, 764.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were placed in calculated positions and refined as riding on their parent atoms [C—H = 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C)].
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C16H26NO+·Cl− |
| M r | 283.83 |
| Crystal system, space group | Orthorhombic, Pna21 |
| Temperature (K) | 293 |
| a, b, c (Å) | 21.8109 (4), 8.2459 (2), 8.8751 (2) |
| V (Å3) | 1596.19 (6) |
| Z | 4 |
| Radiation type | Cu Kα |
| μ (mm−1) | 2.05 |
| Crystal size (mm) | 0.30 × 0.10 × 0.05 |
| Data collection | |
| Diffractometer | Bruker D8 VENTURE dual wavelength Mo/Cu |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.620, 0.754 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 22843, 3168, 3064 |
| R int | 0.034 |
| (sin θ/λ)max (Å−1) | 0.625 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.074, 1.06 |
| No. of reflections | 3168 |
| No. of parameters | 173 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.16, −0.21 |
| Absolute structure | Flack x determined using 1329 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013 ▸) |
| Absolute structure parameter | 0.014 (6) |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989025006772/ev2018sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025006772/ev2018Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989025006772/ev2018Isup3.cml
CCDC reference: 2477070
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
4-Benzyl-4-pentylmorpholin-4-ium chloride. Crystal data
| C16H26NO+·Cl− | Dx = 1.181 Mg m−3 |
| Mr = 283.83 | Melting point: 468(2) K |
| Orthorhombic, Pna21 | Cu Kα radiation, λ = 1.54178 Å |
| a = 21.8109 (4) Å | Cell parameters from 9944 reflections |
| b = 8.2459 (2) Å | θ = 4.1–74.5° |
| c = 8.8751 (2) Å | µ = 2.05 mm−1 |
| V = 1596.19 (6) Å3 | T = 293 K |
| Z = 4 | Plate, colourless |
| F(000) = 616 | 0.30 × 0.10 × 0.05 mm |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Data collection
| Bruker D8 VENTURE dual wavelength Mo/Cu diffractometer | 3168 independent reflections |
| Radiation source: microfocus X-ray source, Incoatec IµS 3.0 Microfocus Source | 3064 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.034 |
| ω–φ scans | θmax = 74.6°, θmin = 4.1° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −27→25 |
| Tmin = 0.620, Tmax = 0.754 | k = −9→10 |
| 22843 measured reflections | l = −11→10 |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.1423P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
| S = 1.06 | Δρmax = 0.16 e Å−3 |
| 3168 reflections | Δρmin = −0.21 e Å−3 |
| 173 parameters | Absolute structure: Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| 1 restraint | Absolute structure parameter: 0.014 (6) |
4-Benzyl-4-pentylmorpholin-4-ium chloride. 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. |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.29346 (3) | 0.33262 (7) | 0.13961 (7) | 0.06703 (18) | |
| O1 | 0.37213 (7) | 0.03995 (18) | 0.55365 (16) | 0.0541 (4) | |
| N4 | 0.31419 (6) | 0.31617 (17) | 0.69908 (18) | 0.0378 (3) | |
| C2 | 0.35629 (9) | 0.0320 (2) | 0.7090 (2) | 0.0489 (4) | |
| H2A | 0.3854 | −0.0368 | 0.7614 | 0.059* | |
| H2B | 0.3159 | −0.0160 | 0.7195 | 0.059* | |
| C3 | 0.35639 (9) | 0.1990 (2) | 0.7799 (2) | 0.0431 (4) | |
| H3A | 0.3978 | 0.2418 | 0.7786 | 0.052* | |
| H3B | 0.3437 | 0.1900 | 0.8843 | 0.052* | |
| C5 | 0.32960 (9) | 0.3091 (2) | 0.5339 (2) | 0.0421 (4) | |
| H5A | 0.3700 | 0.3553 | 0.5177 | 0.050* | |
| H5B | 0.3002 | 0.3736 | 0.4778 | 0.050* | |
| C6 | 0.32864 (10) | 0.1372 (2) | 0.4759 (2) | 0.0492 (4) | |
| H6A | 0.2880 | 0.0919 | 0.4892 | 0.059* | |
| H6B | 0.3380 | 0.1369 | 0.3690 | 0.059* | |
| C7 | 0.24799 (8) | 0.2672 (2) | 0.7317 (2) | 0.0428 (4) | |
| H7A | 0.2441 | 0.1512 | 0.7163 | 0.051* | |
| H7B | 0.2394 | 0.2890 | 0.8370 | 0.051* | |
| C8 | 0.19981 (8) | 0.3526 (2) | 0.6362 (3) | 0.0468 (4) | |
| H8A | 0.2029 | 0.3170 | 0.5323 | 0.056* | |
| H8B | 0.2064 | 0.4689 | 0.6391 | 0.056* | |
| C9 | 0.13639 (8) | 0.3120 (2) | 0.6983 (3) | 0.0502 (5) | |
| H9A | 0.1303 | 0.1956 | 0.6940 | 0.060* | |
| H9B | 0.1343 | 0.3447 | 0.8032 | 0.060* | |
| C10 | 0.08545 (9) | 0.3951 (3) | 0.6118 (3) | 0.0613 (6) | |
| H10A | 0.0858 | 0.3565 | 0.5085 | 0.074* | |
| H10B | 0.0933 | 0.5109 | 0.6098 | 0.074* | |
| C11 | 0.02260 (11) | 0.3655 (4) | 0.6789 (4) | 0.0841 (10) | |
| H11A | −0.0082 | 0.4107 | 0.6139 | 0.126* | |
| H11B | 0.0202 | 0.4160 | 0.7762 | 0.126* | |
| H11C | 0.0159 | 0.2509 | 0.6892 | 0.126* | |
| C12 | 0.32319 (8) | 0.4877 (2) | 0.7628 (2) | 0.0453 (4) | |
| H12A | 0.2952 | 0.5606 | 0.7114 | 0.054* | |
| H12B | 0.3120 | 0.4868 | 0.8685 | 0.054* | |
| C13 | 0.38755 (8) | 0.5547 (2) | 0.7483 (2) | 0.0437 (4) | |
| C14 | 0.42946 (11) | 0.5302 (3) | 0.8635 (3) | 0.0612 (6) | |
| H14 | 0.4180 | 0.4735 | 0.9496 | 0.073* | |
| C15 | 0.48864 (12) | 0.5907 (3) | 0.8500 (4) | 0.0801 (8) | |
| H15 | 0.5172 | 0.5711 | 0.9256 | 0.096* | |
| C16 | 0.50513 (13) | 0.6793 (3) | 0.7253 (5) | 0.0831 (9) | |
| H16 | 0.5449 | 0.7188 | 0.7161 | 0.100* | |
| C17 | 0.46324 (14) | 0.7091 (3) | 0.6154 (4) | 0.0769 (8) | |
| H17 | 0.4742 | 0.7719 | 0.5326 | 0.092* | |
| C18 | 0.40444 (11) | 0.6468 (2) | 0.6257 (3) | 0.0584 (5) | |
| H18 | 0.3762 | 0.6673 | 0.5495 | 0.070* |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0981 (4) | 0.0586 (3) | 0.0444 (2) | 0.0226 (3) | 0.0031 (3) | 0.0032 (3) |
| O1 | 0.0621 (9) | 0.0502 (8) | 0.0500 (8) | 0.0156 (6) | −0.0040 (7) | −0.0115 (6) |
| N4 | 0.0375 (7) | 0.0369 (7) | 0.0389 (8) | 0.0034 (5) | −0.0024 (6) | −0.0031 (6) |
| C2 | 0.0556 (11) | 0.0426 (10) | 0.0483 (11) | 0.0106 (8) | −0.0070 (9) | −0.0021 (9) |
| C3 | 0.0452 (9) | 0.0433 (9) | 0.0409 (9) | 0.0078 (7) | −0.0066 (8) | −0.0025 (8) |
| C5 | 0.0435 (9) | 0.0452 (10) | 0.0376 (9) | 0.0017 (7) | −0.0001 (7) | −0.0011 (7) |
| C6 | 0.0596 (12) | 0.0470 (10) | 0.0409 (10) | 0.0041 (8) | −0.0070 (9) | −0.0069 (8) |
| C7 | 0.0385 (8) | 0.0427 (9) | 0.0473 (9) | 0.0002 (7) | 0.0003 (7) | 0.0010 (8) |
| C8 | 0.0396 (9) | 0.0508 (9) | 0.0501 (9) | 0.0027 (7) | −0.0008 (9) | 0.0026 (10) |
| C9 | 0.0419 (9) | 0.0503 (10) | 0.0583 (12) | −0.0014 (8) | 0.0010 (9) | −0.0007 (9) |
| C10 | 0.0434 (10) | 0.0626 (12) | 0.0780 (17) | 0.0017 (9) | 0.0005 (10) | 0.0120 (11) |
| C11 | 0.0460 (12) | 0.0957 (19) | 0.110 (3) | 0.0070 (11) | 0.0087 (13) | 0.0243 (17) |
| C12 | 0.0468 (9) | 0.0386 (9) | 0.0505 (11) | 0.0034 (7) | −0.0001 (8) | −0.0088 (8) |
| C13 | 0.0460 (9) | 0.0341 (8) | 0.0510 (10) | 0.0011 (7) | 0.0000 (8) | −0.0075 (7) |
| C14 | 0.0660 (13) | 0.0534 (12) | 0.0642 (13) | −0.0100 (10) | −0.0163 (12) | 0.0010 (10) |
| C15 | 0.0621 (14) | 0.0643 (15) | 0.114 (2) | −0.0117 (12) | −0.0296 (15) | −0.0005 (16) |
| C16 | 0.0594 (13) | 0.0580 (14) | 0.132 (3) | −0.0143 (11) | 0.0110 (17) | −0.0100 (16) |
| C17 | 0.0891 (18) | 0.0552 (13) | 0.086 (2) | −0.0174 (12) | 0.0222 (16) | 0.0003 (14) |
| C18 | 0.0734 (14) | 0.0413 (9) | 0.0604 (13) | −0.0024 (9) | −0.0029 (12) | 0.0001 (11) |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Geometric parameters (Å, º)
| O1—C6 | 1.421 (3) | C9—H9A | 0.9700 |
| O1—C2 | 1.423 (2) | C9—H9B | 0.9700 |
| N4—C5 | 1.506 (3) | C10—C11 | 1.515 (3) |
| N4—C3 | 1.515 (2) | C10—H10A | 0.9700 |
| N4—C7 | 1.527 (2) | C10—H10B | 0.9700 |
| N4—C12 | 1.536 (2) | C11—H11A | 0.9600 |
| C2—C3 | 1.514 (3) | C11—H11B | 0.9600 |
| C2—H2A | 0.9700 | C11—H11C | 0.9600 |
| C2—H2B | 0.9700 | C12—C13 | 1.514 (3) |
| C3—H3A | 0.9700 | C12—H12A | 0.9700 |
| C3—H3B | 0.9700 | C12—H12B | 0.9700 |
| C5—C6 | 1.508 (3) | C13—C18 | 1.378 (3) |
| C5—H5A | 0.9700 | C13—C14 | 1.386 (3) |
| C5—H5B | 0.9700 | C14—C15 | 1.389 (3) |
| C6—H6A | 0.9700 | C14—H14 | 0.9300 |
| C6—H6B | 0.9700 | C15—C16 | 1.374 (5) |
| C7—C8 | 1.522 (3) | C15—H15 | 0.9300 |
| C7—H7A | 0.9700 | C16—C17 | 1.359 (5) |
| C7—H7B | 0.9700 | C16—H16 | 0.9300 |
| C8—C9 | 1.526 (3) | C17—C18 | 1.384 (4) |
| C8—H8A | 0.9700 | C17—H17 | 0.9300 |
| C8—H8B | 0.9700 | C18—H18 | 0.9300 |
| C9—C10 | 1.514 (3) | ||
| C6—O1—C2 | 109.55 (15) | C10—C9—C8 | 112.49 (18) |
| C5—N4—C3 | 107.53 (14) | C10—C9—H9A | 109.1 |
| C5—N4—C7 | 112.67 (14) | C8—C9—H9A | 109.1 |
| C3—N4—C7 | 108.43 (14) | C10—C9—H9B | 109.1 |
| C5—N4—C12 | 111.44 (14) | C8—C9—H9B | 109.1 |
| C3—N4—C12 | 109.60 (13) | H9A—C9—H9B | 107.8 |
| C7—N4—C12 | 107.12 (13) | C9—C10—C11 | 113.1 (2) |
| O1—C2—C3 | 111.15 (17) | C9—C10—H10A | 109.0 |
| O1—C2—H2A | 109.4 | C11—C10—H10A | 109.0 |
| C3—C2—H2A | 109.4 | C9—C10—H10B | 109.0 |
| O1—C2—H2B | 109.4 | C11—C10—H10B | 109.0 |
| C3—C2—H2B | 109.4 | H10A—C10—H10B | 107.8 |
| H2A—C2—H2B | 108.0 | C10—C11—H11A | 109.5 |
| C2—C3—N4 | 112.47 (14) | C10—C11—H11B | 109.5 |
| C2—C3—H3A | 109.1 | H11A—C11—H11B | 109.5 |
| N4—C3—H3A | 109.1 | C10—C11—H11C | 109.5 |
| C2—C3—H3B | 109.1 | H11A—C11—H11C | 109.5 |
| N4—C3—H3B | 109.1 | H11B—C11—H11C | 109.5 |
| H3A—C3—H3B | 107.8 | C13—C12—N4 | 115.05 (14) |
| N4—C5—C6 | 111.45 (16) | C13—C12—H12A | 108.5 |
| N4—C5—H5A | 109.3 | N4—C12—H12A | 108.5 |
| C6—C5—H5A | 109.3 | C13—C12—H12B | 108.5 |
| N4—C5—H5B | 109.3 | N4—C12—H12B | 108.5 |
| C6—C5—H5B | 109.3 | H12A—C12—H12B | 107.5 |
| H5A—C5—H5B | 108.0 | C18—C13—C14 | 119.1 (2) |
| O1—C6—C5 | 110.81 (16) | C18—C13—C12 | 121.06 (19) |
| O1—C6—H6A | 109.5 | C14—C13—C12 | 119.7 (2) |
| C5—C6—H6A | 109.5 | C13—C14—C15 | 119.8 (3) |
| O1—C6—H6B | 109.5 | C13—C14—H14 | 120.1 |
| C5—C6—H6B | 109.5 | C15—C14—H14 | 120.1 |
| H6A—C6—H6B | 108.1 | C16—C15—C14 | 120.2 (3) |
| C8—C7—N4 | 115.16 (16) | C16—C15—H15 | 119.9 |
| C8—C7—H7A | 108.5 | C14—C15—H15 | 119.9 |
| N4—C7—H7A | 108.5 | C17—C16—C15 | 119.9 (2) |
| C8—C7—H7B | 108.5 | C17—C16—H16 | 120.1 |
| N4—C7—H7B | 108.5 | C15—C16—H16 | 120.1 |
| H7A—C7—H7B | 107.5 | C16—C17—C18 | 120.6 (3) |
| C7—C8—C9 | 108.86 (19) | C16—C17—H17 | 119.7 |
| C7—C8—H8A | 109.9 | C18—C17—H17 | 119.7 |
| C9—C8—H8A | 109.9 | C13—C18—C17 | 120.3 (2) |
| C7—C8—H8B | 109.9 | C13—C18—H18 | 119.9 |
| C9—C8—H8B | 109.9 | C17—C18—H18 | 119.9 |
| H8A—C8—H8B | 108.3 | ||
| C6—O1—C2—C3 | −60.6 (2) | C8—C9—C10—C11 | −175.9 (2) |
| O1—C2—C3—N4 | 56.3 (2) | C5—N4—C12—C13 | −59.3 (2) |
| C5—N4—C3—C2 | −51.0 (2) | C3—N4—C12—C13 | 59.6 (2) |
| C7—N4—C3—C2 | 71.1 (2) | C7—N4—C12—C13 | 176.99 (16) |
| C12—N4—C3—C2 | −172.25 (16) | N4—C12—C13—C18 | 92.4 (2) |
| C3—N4—C5—C6 | 52.57 (19) | N4—C12—C13—C14 | −90.8 (2) |
| C7—N4—C5—C6 | −66.85 (19) | C18—C13—C14—C15 | −3.6 (3) |
| C12—N4—C5—C6 | 172.70 (15) | C12—C13—C14—C15 | 179.6 (2) |
| C2—O1—C6—C5 | 62.8 (2) | C13—C14—C15—C16 | 2.2 (4) |
| N4—C5—C6—O1 | −60.2 (2) | C14—C15—C16—C17 | 0.6 (4) |
| C5—N4—C7—C8 | −50.2 (2) | C15—C16—C17—C18 | −2.0 (4) |
| C3—N4—C7—C8 | −169.13 (16) | C14—C13—C18—C17 | 2.3 (3) |
| C12—N4—C7—C8 | 72.7 (2) | C12—C13—C18—C17 | 179.0 (2) |
| N4—C7—C8—C9 | −171.03 (16) | C16—C17—C18—C13 | 0.5 (4) |
| C7—C8—C9—C10 | 178.75 (19) |
4-Benzyl-4-pentylmorpholin-4-ium chloride. Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the benzene ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2B···Cl1i | 0.97 | 2.78 | 3.708 (2) | 160 |
| C3—H3B···Cl1ii | 0.97 | 2.78 | 3.645 (2) | 149 |
| C6—H6B···Cl1 | 0.97 | 2.77 | 3.477 (2) | 130 |
| C12—H12B···Cl1ii | 0.97 | 2.75 | 3.639 (2) | 153 |
| C15—H15···Cg1iii | 0.93 | 3.28 | 4.104 (3) | 149 |
Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x, y, z+1; (iii) −x+1, −y+1, z+1/2.
Funding Statement
This work was carried out within the framework of the Basic Scientific Research Program of the Academy of Sciences of the Republic of Uzbekistan.
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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/S2056989025006772/ev2018sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025006772/ev2018Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989025006772/ev2018Isup3.cml
CCDC reference: 2477070
Additional supporting information: crystallographic information; 3D view; checkCIF report