Synthesis and crystal structure of 4-benzyl-4-pentyl­morpholin-4-ium chloride

Yakhshilikova, Z.; Kholikov, T.; Zhurakulov, S.; Turgunov, K.

doi:10.1107/S2056989025006772

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 797-800

https://doi.org/10.1107/S2056989025006772

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Synthesis and crystal structure of 4-benzyl-4-pentylmorpholin-4-ium chloride

Zarifa Yakhshilikova,^a Tursunali Kholikov,^a Sherzod Zhurakulov ^b and Kambarali Turgunov ^b,^c ^*

^aNational University of Uzbekistan named after Mirzo Ulugbek, University Str, 4., Tashkent, 100174, Uzbekistan, ^bS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan, and ^cTurin Polytechnic University in Tashkent, Kichik Khalka yuli str. 17, 100095 Tashkent, Uzbekistan
^*Correspondence e-mail: [email protected]

Edited by S. P. Kelley, University of Missouri-Columbia, USA (Received 15 May 2025; accepted 30 July 2025; online 5 August 2025)

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.

Keywords: crystal structure; molecular structure; N-pentyl morpholine; benzyl chloride; quaternary morpholine halide.

CCDC reference: 2477070

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.

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

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 C_ar—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, ν_max, 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, ν_max, 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 U_iso(H) = 1.2U_eq(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 )
T_min, T_max	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
Δρ_max, Δρ_min (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)
Computer programs: APEX5 (Bruker, 2023 ), SAINT (Bruker, 2019 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2477070

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025006772/ev2018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006772/ev2018Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025006772/ev2018Isup3.cml

checkCIF report

Computing details top

4-Benzyl-4-pentylmorpholin-4-ium chloride top

Crystal data top

C₁₆H₂₆NO⁺·Cl⁻	D_x = 1.181 Mg m⁻³
M_r = 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

Data collection top

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	R_int = 0.034
ω–φ scans	θ_max = 74.6°, θ_min = 4.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −27→25
T_min = 0.620, T_max = 0.754	k = −9→10
22843 measured reflections	l = −11→10

Refinement top

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(F_o²) + (0.039P)² + 0.1423P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.074	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.16 e Å⁻³
3168 reflections	Δρ_min = −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)

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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 information

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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