Crystal structures of (S)-3-{1-[(4-chloro­phen­yl)sulfon­yl]piperidin-2-yl}pyridine, (S)-3-[1-(4-methyl­phen­yl)piperidin-2-yl]pyridine, (S)-3-{1-[(4-meth­oxy­phen­yl)sulfon­yl]piperidin-2-yl}pyridine and (S)-3-{1-[(3,4-di­methyl­phen­yl)sulfon­yl]piperidin-2-yl}pyridine

Okmanov, R.Y.; Olimova, M.I.; Yuldashova, I.E.; Azimova, G.Z.; Pulatova, F.A.

doi:10.1107/S2056989026004524

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Volume 82| Part 6| June 2026|

https://doi.org/10.1107/S2056989026004524

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Crystal structures of (S)-3-{1-[(4-chlorophenyl)sulfonyl]piperidin-2-yl}pyridine, (S)-3-[1-(4-methylphenyl)piperidin-2-yl]pyridine, (S)-3-{1-[(4-methoxyphenyl)sulfonyl]piperidin-2-yl}pyridine and (S)-3-{1-[(3,4-dimethylphenyl)sulfonyl]piperidin-2-yl}pyridine

R. Ya. Okmanov,^a ^* M. I. Olimova,^a I. E. Yuldashova,^a G. Z. Azimova ^b and F. A. Pulatova ^c

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek str., 77, Tashkent, 100170, Uzbekistan, ^bNational University of Uzbekistan named after Mirzo Ulugbek, Universitet str., 4, Almazar district, Tashkent, 100174, Uzbekistan, and ^cTashkent Pharmaceutical institute, Mirabad district, Aybek str., 45, Tashkent, 100015, Uzbekistan
^*Correspondence e-mail: [email protected]

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 24 February 2026; accepted 29 April 2026; online 7 May 2026)

In the presence of trimethylamine, new compounds were obtained by arylsulfonylation of 3-(piperidin-2-yl)pyridine (the alkaloid anabasine), namely: (S)-3-{1-[(4-chlorophenyl)sulfonyl]piperidin-2-yl}pyridine, C₁₆H₁₇ClN₂O₂S (1); (S)-3-[1-(4-methylphenyl)piperidin-2-yl]pyridine, C₁₇H₂₀N₂O₂S (2); (S)-3-{1-[(4-methoxyphenyl)sulfonyl]piperidin-2-yl}pyridine, C₁₇H₂₀N₂O₃S (3); and (S)-3-{1-[(3,4-dimethylphenyl)sulfonyl]piperidin-2-yl}pyridine, C₁₈H₂₂N₂O₂S (4). In the crystal structures, the spatial arrangement of the pyridine and piperidine rings around the Csp²—C* bond, as well as the orientation of the benzene ring of the arylsulfonyl group relative to the anabasine moiety, are analyzed.

Keywords: alkaloid anabazin; 3-(piperidin-2-yl)pyridine; arylsulfonyl; crystal structure.

CCDC references: 2550374; 2550373; 2550372; 2550371

1. Chemical context

Alkaloids are natural organic compounds containing nitrogen atoms that are synthesized by plants. They play an important role in pharmacology, toxicology, and medicinal chemistry (Dewick, 2009 ; Daly, 2005 ).

Anabasine (C₁₀H₁₄N₂) is a natural alkaloid with a pyridine–piperidine structure, primarily found in Anabasis aphylla L. (Ujváry, 2010 ). Pharmacological studies have shown that anabasine exhibits a stimulating effect at low doses, whereas at high doses it produces strong toxic effects. High concentrations may lead to paralysis of the nervous system, depression of the respiratory center, and death (Kuete, 2014 ). For this reason, anabasine is classified as a toxic alkaloid and its use is restricted. Historically, anabasine was used as an insecticide in agriculture; however, due to its high toxicity, it is not widely applied in practice today (Amtaghri et al., 2025 ).

In addition to being isolated from plants, synthetic methods for obtaining anabasine have also been developed (Felpin et al., 2000 ). Numerous reactions have been carried out based on anabasine, most of which are focused on the synthesis of N-derivatives (Kulakov, 2010 ; Slyn'ko et al., 2013 ; Bakbardina et al., 2006 ). Although the main objective of these studies has been the synthesis of new biologically active compounds, particular emphasis has been placed on obtaining less toxic and biologically selective derivatives (Mukusheva et al., 2022 ; Artyushin et al., 2016 ).

Arylsulfonylation reactions are typically carried out at room temperature in various solvents in the presence of triethylamine or sodium hydroxide. According to the literature, the reaction time varies, mainly depending on the reactivity of the reagents involved. Structural studies of the synthesized arylsulfonyl products using X-ray crystallographic analysis have provided interesting and distinctive results (Abdireymov et al., 2011 ; Okmanov et al., 2022 , 2023 ).

2. Structural commentary

The asymmetric unit of all the structures consists of a single molecule (Fig. 1). In the anabasine fragment, the piperidine rings adopt a chair conformation, and the spatial orientation of the pyridine ring relative to it is observed to be axial. In structures 1–4, the relative arrangement of the pyridine and piperidine rings around the Csp²—C* bond differs slightly. This can be explained by the values of the N1′—C*—C—C torsion angles. The torsion angle values are 34.0 (4)° for 1, 31.3 (4)° for 2, 25.2 (5)° for 3, and 28.4 (5)° for 4. According to literature sources, in anabasine derivatives with various substituents, these torsion angles range from 17 to 82° (Kulakov et al., 2010 ; Wojciechowska-Nowak et al., 2007 ).

Figure 1
The molecular structures of the title compounds drawn at 50% probability ellipsoids.

When comparing the N(pyridine)⋯N(piperidine) distances in the anabasine fragment, it is observed that they are very similar: 4.799 (4) Å for 1, 4.819 (4) Å for 2, 4.833 (5) Å for 3, and 4.832 (4) Å for 4. In other anabasine derivatives, depending on the spatial arrangement of the piperidine and pyridine rings, the N⋯N distances have been reported to range from 4.29 to 4.86 Å (Wojciechowska-Nowak et al., 2007).

In studies by Wojciechowska-Nowak et al. on the structures of salts of anabasine derivatives, four conformations were proposed based on the arrangement of the piperidine and pyridine rings. The N-arylsulfonyl anabasine derivatives 1–4 studied here differ from the proposed conformations (Fig. 2).

Figure 2
The spatial arrangement of the pyridine and piperidine rings in N-arylsulfonyl anabasine (1–4)

The position of the arylsulfonyl group relative to the piperidine ring in structures (around the N1—S1 and S1—C7 bonds) is nearly identical. The mutual arrangement of the piperidine and benzene rings was analyzed using the C2′—N1′—S1—O1 and O1—S1—C7—C12 torsion angles, which are 34.8 (2) and −24.4 (3)° for 1, 33.7 (2) and −31.5 (3)° for 2, 37.2 (4) and −24.0 (4)° for 3, and 35.6 (3) and −32.3 (3)° for 4, respectively. In all structures, such an arrangement of groups can be explained by the presence of intramolecular hydrogen bonding.

The mutual arrangement of planar aromatic rings relative to the six-membered saturated heterocycle in compounds 2–4 is nearly identical. The nature of intermolecular van der Waals contacts in these structures is also similar, indicating the formation of isostructural crystals in the packing (space group P2₁2₁2₁) with identical unit-cell parameters (Table 5).

It was established that in the crystal structures, the similar arrangement of the piperidine ring and the benzene ring connected via the sulfonyl group is due to intermolecular interactions. Substituents on the benzene ring (Cl, CH₃, OCH₃) do not significantly affect the mutual arrangement of the rings.

3. Supramolecular features

The analysis of intermolecular interactions in all studied structures revealed only weak hydrogen bonding, which plays a key role in consolidating the crystal packing (Tables 1–4 , Figs. 3–6 ).

Table 1
Hydrogen-bond geometry (Å, °) for 1

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.58	3.383 (4)	145
C3′—H3′B⋯Cl1ⁱⁱ	0.97	2.98	3.923 (4)	163
C8—H8⋯Cl1ⁱⁱⁱ	0.93	2.97	3.807 (3)	150
C2′—H2′A⋯O1	0.98	2.38	2.880 (4)	111
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for 2

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.62	3.474 (4)	152
C5′—H5′A⋯O1ⁱⁱ	0.97	2.51	3.369 (4)	147
C2′—H2′A⋯O1	0.98	2.37	2.884 (4)	112
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) .

Table 3
Hydrogen-bond geometry (Å, °) for 3

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.47	3.252 (5)	142
C5′—H5′A⋯O1ⁱⁱ	0.97	2.49	3.298 (5)	140
C2′—H2′A⋯O1	0.98	2.37	2.880 (5)	111
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) .

Table 4
Hydrogen-bond geometry (Å, °) for 4

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5′—H5′A⋯O1ⁱ	0.97	2.60	3.462 (5)	148
C5—H5⋯O1ⁱⁱ	0.93	2.64	3.384 (5)	138
C2′—H2′A⋯O1	0.98	2.39	2.892 (4)	111
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 3
Observed intermolecular O1⋯Cl1 contacts in the crystal structure of 1 (the molecules are linked along the c-axis direction).

Figure 4
Observed intermolecular C12—H12⋯O2 interactions in the crystal structure of 2 (the molecules are linked along the b-axis direction).

Figure 5
Observed intermolecular C12—H12⋯O2 interactions in the crystal structure of 3 (the molecules are linked along the b-axis direction).

Figure 6
Observed intermolecular C5′—H5′A⋯O1 interactions in the crystal structure of 4 (the molecules are linked along the a-axis direction).

A consistent intramolecular C—H⋯O hydrogen bond was observed to consolidate the molecular conformation in the solid state. This interaction involves the piperidine ring via the asymmetric carbon atom and the oxygen atom of the SO₂ group (C2′—H2'A⋯O1).

In the crystal structure of compound 1, an infinite ribbon is formed along the c-axis direction, driven by donor–acceptor interactions between the oxygen atom of the SO₂ group and the chlorine atom at the C10 position [Cl⋯O distance = 3.127 (2) Å; symmetry operation: $[{3\over 2}]$ − x, 2 − y, − $[{1\over 2}]$ + z; Fig. 3). These ribbons are further interconnected along the a-axis direction through intermolecular C12—H12⋯O2 hydrogen bonds. Additionally, the chlorine atom participates in weak C–H⋯Cl (C3′—H3′B⋯Cl1 and C8—H8⋯Cl1) hydrogen bonding interactions.

In the crystal structures of compounds 2 and 3, similar intermolecular hydrogen bonding patterns are observed, where molecules are linked along the b-axis direction via C12—H12⋯O2 interactions (Figs. 4 and 5). The resulting chains are further consolidated by C5′—H5′A⋯O1 hydrogen bonds. In the crystal structure of 4, this type of interaction leads to the formation of molecular chains along the a-axis direction (Fig. 6). In contrast to the previous structures, the chains in structure 4 are interconnected via intermolecular C5—H5⋯O1 hydrogen bonds.

4. Database survey

A search of anabasine derivatives in the Cambridge Structural Database (CSD, updated to November 2025; Groom et al., 2016 ) yielded 37 results. Of them, 13 are N-derivatives of anabasin alkaloids.

The axial orientation of the pyridine ring is observed in the crystal structures of N-ethyl-2-(pyridin-3-yl)piperidine-1-carbothioamide (ATUGAZ; Nurkenov et al., 2016 ) and 2-(pyridin-3-yl)-N-[2-(vinyloxy)ethyl]piperidine-1-carbothiamide (QELPON; Ibraev et al., 2006 ).

Structurally similar compounds in terms of the orientation of the pyridine ring relative to the piperidine ring and the distance between the nitrogen atoms are N-(anabasinyl-1-carbonothioyl)-2-furamide (FUSKUA; Kulakov et al., 2009 ) and 2-(pyridin-3-yl)-N-[2-(vinyloxy)ethyl]piperidine-1-carbothiamide (QELPON; Ibraev et al., 2006).

5. Synthesis and crystallization

(S)-3-{1-[(4-Chlorophenyl)sulfonyl]piperidin-2-yl}pyridine (1), (S)-3-[1-(4-methylphenyl)piperidin-2-yl]pyridine (2), (S)-3-{1-[(4-methoxyphenyl)sulfonyl]piperidin-2-yl}pyridine (3), and (S)-3-{1-[(3,4-dimethylphenyl)sulfonyl]piperidin-2-yl}pyridine (4) were synthesized according to the reported method (Olimova et al., 2025 ). Colourless single crystals of the compounds, suitable for X-ray diffraction analysis, were successfully obtained from ethanol.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. All hydrogen atoms were found in difference maps and then freely refined with isotropic shift parameters, resulting in C—H distances of 0.97 Å for CH₂, 0.96 Å for CH₃ and 0.93 Å for C_ar.

Table 5
Experimental details

	1	2	3	4
Crystal data
Chemical formula	C₁₆H₁₇ClN₂O₂S	C₁₇H₂₀N₂O₂S	C₁₇H₂₀N₂O₃S	C₁₈H₂₂N₂O₂S
M_r	336.83	316.41	332.41	330.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁
Temperature (K)	294	297	297	295
a, b, c (Å)	10.694 (2), 10.715 (2), 14.110 (3)	7.8933 (16), 11.408 (2), 18.195 (4)	7.9758 (16), 11.131 (2), 18.754 (4)	7.9087 (16), 11.737 (2), 18.117 (4)
V (Å³)	1616.8 (6)	1638.5 (6)	1664.9 (6)	1681.6 (6)
Z	4	4	4	4
Radiation type	Cu Kα	Cu Kα	Cu Kα	Cu Kα
μ (mm⁻¹)	3.37	1.82	1.87	1.80
Crystal size (mm)	0.50 × 0.45 × 0.30	0.45 × 0.30 × 0.25	0.30 × 0.25 × 0.25	0.45 × 0.25 × 0.22

Data collection
Diffractometer	Bruker D8 VENTURE dual wavelength Mo/Cu	Xcalibur, Ruby	Xcalibur, Ruby	Xcalibur, Ruby
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.32, 0.43	0.79, 1.00	0.78, 1.00	0.88, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	50181, 3234, 3222	11987, 3372, 3194	12142, 3427, 2899	12220, 3428, 2886
R_int	0.029	0.033	0.048	0.045
(sin θ/λ)_max (Å⁻¹)	0.625	0.630	0.629	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.06	0.051, 0.123, 1.12	0.054, 0.133, 1.10	0.045, 0.111, 1.07
No. of reflections	3234	3372	3427	3428
No. of parameters	199	200	209	210
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.44	0.33, −0.63	0.23, −0.53	0.21, −0.34
Absolute structure	Flack x determined using 1346 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )	Flack x determined using 1275 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)	Flack x determined using 1030 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)	Flack x determined using 1007 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.094 (3)	0.005 (8)	−0.014 (15)	0.011 (14)
Computer programs: APEX5 and SAINT (Bruker, 2012 ), CrysAlis PRO (Rigaku OD, 2021 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), XP in SHELXTL (Sheldrick, 2008 ), Mercury (Macrae et al., 2020 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 2550374; 2550373; 2550372; 2550371

Crystal structure: contains datablocks 1, 2, 3, 4, manuscript. DOI: https://doi.org/10.1107/S2056989026004524/dx2068sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989026004524/dx20681sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989026004524/dx20682sup3.hkl

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989026004524/dx20683sup4.hkl

Structure factors: contains datablock 4. DOI: https://doi.org/10.1107/S2056989026004524/dx20684sup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004524/dx20681sup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004524/dx20682sup7.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004524/dx20683sup8.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004524/dx20684sup9.cml

checkCIF report

Computing details top

(S)-3-{1-[(4-Chlorophenyl)sulfonyl]piperidin-2-yl}pyridine (1) top

Crystal data top

C₁₆H₁₇ClN₂O₂S	D_x = 1.384 Mg m⁻³
M_r = 336.83	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9773 reflections
a = 10.694 (2) Å	θ = 4.1–74.2°
b = 10.715 (2) Å	µ = 3.37 mm⁻¹
c = 14.110 (3) Å	T = 294 K
V = 1616.8 (6) Å³	Prism, colourless
Z = 4	0.50 × 0.45 × 0.30 mm
F(000) = 704

Data collection top

Bruker D8 VENTURE dual wavelength Mo/Cu diffractometer	3234 independent reflections
Radiation source: microfocus sealed X-ray tube, INCOATEC IµS	3222 reflections with I > 2σ(I)
Detector resolution: 7.39 pixels mm^-1	R_int = 0.029
φ and ω scans	θ_max = 74.4°, θ_min = 5.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −13→13
T_min = 0.32, T_max = 0.43	k = −13→13
50181 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0574P)² + 0.4484P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3234 reflections	Δρ_max = 0.30 e Å⁻³
199 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1346 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.094 (3)

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
S1	0.78885 (6)	0.66179 (6)	0.48625 (4)	0.04518 (19)
Cl1	0.82268 (11)	1.15407 (11)	0.25168 (8)	0.0926 (4)
O1	0.7158 (3)	0.6849 (2)	0.56915 (13)	0.0642 (6)
O2	0.9117 (2)	0.6108 (2)	0.4948 (2)	0.0731 (7)
N1	0.3482 (4)	0.3020 (4)	0.4288 (3)	0.0849 (11)
N1'	0.7089 (2)	0.5681 (2)	0.41990 (15)	0.0406 (5)
C2	0.4014 (3)	0.4113 (4)	0.4065 (3)	0.0643 (9)
H2	0.359882	0.463138	0.364013	0.077*
C3	0.5152 (3)	0.4518 (3)	0.4432 (2)	0.0457 (6)
C4	0.5723 (4)	0.3748 (3)	0.5077 (2)	0.0620 (8)
H4	0.646868	0.398968	0.536173	0.074*
C5	0.5184 (5)	0.2607 (4)	0.5303 (3)	0.0776 (11)
H5	0.557477	0.206614	0.572456	0.093*
C6	0.4083 (5)	0.2297 (4)	0.4899 (4)	0.0817 (13)
H6	0.372584	0.153400	0.505841	0.098*
C2'	0.5711 (2)	0.5783 (3)	0.4172 (2)	0.0450 (6)
H2'A	0.545691	0.638507	0.465762	0.054*
C3'	0.5304 (4)	0.6293 (4)	0.3211 (3)	0.0808 (13)
H3'A	0.557074	0.715537	0.315568	0.097*
H3'B	0.439910	0.627501	0.317113	0.097*
C4'	0.5852 (5)	0.5542 (6)	0.2392 (3)	0.0984 (18)
H4'A	0.554452	0.469097	0.241802	0.118*
H4'B	0.559108	0.590475	0.179400	0.118*
C5'	0.7247 (5)	0.5543 (5)	0.2453 (3)	0.0894 (14)
H5'A	0.755575	0.638741	0.237147	0.107*
H5'B	0.758889	0.503317	0.194713	0.107*
C6'	0.7677 (3)	0.5041 (3)	0.3396 (2)	0.0599 (8)
H6'A	0.748388	0.415765	0.342963	0.072*
H6'B	0.857766	0.513171	0.344197	0.072*
C7	0.8030 (2)	0.8051 (2)	0.42494 (19)	0.0424 (5)
C8	0.9004 (3)	0.8207 (3)	0.3612 (3)	0.0574 (8)
H8	0.960987	0.759082	0.354115	0.069*
C9	0.9062 (4)	0.9289 (4)	0.3083 (3)	0.0680 (9)
H9	0.970115	0.940354	0.264489	0.082*
C10	0.8171 (3)	1.0196 (3)	0.3209 (2)	0.0587 (8)
C11	0.7225 (3)	1.0061 (3)	0.3849 (3)	0.0596 (7)
H11	0.663730	1.069156	0.393154	0.071*
C12	0.7150 (3)	0.8969 (3)	0.4374 (2)	0.0522 (6)
H12	0.650597	0.885872	0.480863	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0438 (3)	0.0471 (3)	0.0446 (3)	−0.0057 (3)	−0.0095 (3)	0.0027 (3)
Cl1	0.0952 (8)	0.0797 (6)	0.1027 (8)	−0.0302 (6)	−0.0210 (6)	0.0445 (6)
O1	0.0915 (16)	0.0653 (13)	0.0358 (9)	−0.0170 (13)	0.0048 (11)	−0.0063 (9)
O2	0.0457 (11)	0.0698 (14)	0.104 (2)	0.0008 (10)	−0.0306 (13)	0.0130 (14)
N1	0.080 (2)	0.079 (2)	0.096 (2)	−0.0393 (18)	0.008 (2)	−0.007 (2)
N1'	0.0352 (10)	0.0437 (11)	0.0430 (10)	−0.0005 (9)	0.0010 (9)	−0.0058 (9)
C2	0.0530 (17)	0.067 (2)	0.073 (2)	−0.0170 (16)	−0.0035 (16)	0.0014 (17)
C3	0.0430 (13)	0.0475 (14)	0.0467 (13)	−0.0068 (11)	0.0072 (11)	−0.0054 (11)
C4	0.0677 (19)	0.0587 (17)	0.0595 (18)	−0.0078 (14)	0.0022 (15)	0.0091 (15)
C5	0.099 (3)	0.062 (2)	0.072 (2)	−0.007 (2)	0.017 (2)	0.0197 (19)
C6	0.102 (3)	0.061 (2)	0.082 (3)	−0.027 (2)	0.030 (2)	−0.001 (2)
C2'	0.0352 (12)	0.0430 (13)	0.0568 (15)	−0.0002 (10)	−0.0013 (11)	0.0011 (12)
C3'	0.060 (2)	0.076 (2)	0.106 (3)	−0.0196 (18)	−0.034 (2)	0.042 (2)
C4'	0.114 (4)	0.135 (4)	0.0460 (18)	−0.056 (3)	−0.025 (2)	0.022 (2)
C5'	0.115 (3)	0.107 (3)	0.0457 (17)	−0.044 (3)	0.015 (2)	−0.0083 (19)
C6'	0.0606 (19)	0.0631 (18)	0.0559 (16)	−0.0027 (15)	0.0172 (14)	−0.0162 (14)
C7	0.0364 (12)	0.0451 (12)	0.0457 (12)	−0.0089 (10)	−0.0044 (10)	0.0014 (10)
C8	0.0390 (13)	0.0601 (18)	0.0731 (19)	−0.0042 (13)	0.0102 (13)	0.0010 (15)
C9	0.0545 (18)	0.078 (2)	0.071 (2)	−0.0210 (17)	0.0160 (16)	0.0097 (18)
C10	0.0556 (18)	0.0560 (16)	0.0646 (18)	−0.0188 (14)	−0.0127 (14)	0.0121 (14)
C11	0.0514 (17)	0.0506 (15)	0.077 (2)	0.0018 (14)	−0.0025 (16)	0.0047 (15)
C12	0.0436 (13)	0.0533 (15)	0.0597 (16)	−0.0031 (12)	0.0055 (13)	−0.0002 (12)

Geometric parameters (Å, º) top

S1—O2	1.428 (2)	C3'—H3'A	0.9700
S1—O1	1.428 (2)	C3'—H3'B	0.9700
S1—N1'	1.617 (2)	C4'—C5'	1.494 (8)
S1—C7	1.769 (3)	C4'—H4'A	0.9700
Cl1—C10	1.741 (3)	C4'—H4'B	0.9700
N1—C6	1.326 (7)	C5'—C6'	1.507 (6)
N1—C2	1.339 (5)	C5'—H5'A	0.9700
N1'—C6'	1.466 (3)	C5'—H5'B	0.9700
N1'—C2'	1.478 (3)	C6'—H6'A	0.9700
C2—C3	1.392 (4)	C6'—H6'B	0.9700
C2—H2	0.9300	C7—C12	1.372 (4)
C3—C4	1.371 (5)	C7—C8	1.387 (4)
C3—C2'	1.526 (4)	C8—C9	1.380 (5)
C4—C5	1.389 (5)	C8—H8	0.9300
C4—H4	0.9300	C9—C10	1.373 (6)
C5—C6	1.350 (7)	C9—H9	0.9300
C5—H5	0.9300	C10—C11	1.364 (5)
C6—H6	0.9300	C11—C12	1.387 (4)
C2'—C3'	1.525 (5)	C11—H11	0.9300
C2'—H2'A	0.9800	C12—H12	0.9300
C3'—C4'	1.525 (8)

O2—S1—O1	120.04 (18)	C5'—C4'—C3'	109.8 (3)
O2—S1—N1'	107.32 (14)	C5'—C4'—H4'A	109.7
O1—S1—N1'	107.00 (14)	C3'—C4'—H4'A	109.7
O2—S1—C7	107.15 (14)	C5'—C4'—H4'B	109.7
O1—S1—C7	107.28 (14)	C3'—C4'—H4'B	109.7
N1'—S1—C7	107.51 (12)	H4'A—C4'—H4'B	108.2
C6—N1—C2	117.2 (4)	C4'—C5'—C6'	110.8 (3)
C6'—N1'—C2'	116.2 (2)	C4'—C5'—H5'A	109.5
C6'—N1'—S1	120.7 (2)	C6'—C5'—H5'A	109.5
C2'—N1'—S1	119.75 (18)	C4'—C5'—H5'B	109.5
N1—C2—C3	123.8 (4)	C6'—C5'—H5'B	109.5
N1—C2—H2	118.1	H5'A—C5'—H5'B	108.1
C3—C2—H2	118.1	N1'—C6'—C5'	112.6 (3)
C4—C3—C2	116.6 (3)	N1'—C6'—H6'A	109.1
C4—C3—C2'	121.3 (3)	C5'—C6'—H6'A	109.1
C2—C3—C2'	122.0 (3)	N1'—C6'—H6'B	109.1
C3—C4—C5	119.8 (4)	C5'—C6'—H6'B	109.1
C3—C4—H4	120.1	H6'A—C6'—H6'B	107.8
C5—C4—H4	120.1	C12—C7—C8	120.8 (3)
C6—C5—C4	118.8 (4)	C12—C7—S1	120.1 (2)
C6—C5—H5	120.6	C8—C7—S1	119.1 (2)
C4—C5—H5	120.6	C9—C8—C7	119.0 (3)
N1—C6—C5	123.7 (4)	C9—C8—H8	120.5
N1—C6—H6	118.2	C7—C8—H8	120.5
C5—C6—H6	118.2	C10—C9—C8	119.6 (3)
N1'—C2'—C3'	109.5 (3)	C10—C9—H9	120.2
N1'—C2'—C3	108.6 (2)	C8—C9—H9	120.2
C3'—C2'—C3	114.9 (3)	C11—C10—C9	121.7 (3)
N1'—C2'—H2'A	107.9	C11—C10—Cl1	119.0 (3)
C3'—C2'—H2'A	107.9	C9—C10—Cl1	119.3 (3)
C3—C2'—H2'A	107.9	C10—C11—C12	119.1 (3)
C2'—C3'—C4'	112.0 (3)	C10—C11—H11	120.5
C2'—C3'—H3'A	109.2	C12—C11—H11	120.5
C4'—C3'—H3'A	109.2	C7—C12—C11	119.8 (3)
C2'—C3'—H3'B	109.2	C7—C12—H12	120.1
C4'—C3'—H3'B	109.2	C11—C12—H12	120.1
H3'A—C3'—H3'B	107.9

O2—S1—N1'—C6'	−36.4 (3)	C3—C2'—C3'—C4'	−69.6 (4)
O1—S1—N1'—C6'	−166.5 (2)	C2'—C3'—C4'—C5'	−57.9 (5)
C7—S1—N1'—C6'	78.6 (3)	C3'—C4'—C5'—C6'	56.6 (5)
O2—S1—N1'—C2'	164.8 (2)	C2'—N1'—C6'—C5'	50.8 (4)
O1—S1—N1'—C2'	34.8 (2)	S1—N1'—C6'—C5'	−108.7 (3)
C7—S1—N1'—C2'	−80.2 (2)	C4'—C5'—C6'—N1'	−52.9 (5)
C6—N1—C2—C3	0.4 (6)	O2—S1—C7—C12	−154.5 (2)
N1—C2—C3—C4	−1.8 (5)	O1—S1—C7—C12	−24.4 (3)
N1—C2—C3—C2'	−178.9 (3)	N1'—S1—C7—C12	90.4 (2)
C2—C3—C4—C5	2.4 (5)	O2—S1—C7—C8	28.5 (3)
C2'—C3—C4—C5	179.6 (3)	O1—S1—C7—C8	158.6 (2)
C3—C4—C5—C6	−1.9 (6)	N1'—S1—C7—C8	−86.6 (3)
C2—N1—C6—C5	0.2 (7)	C12—C7—C8—C9	−1.6 (5)
C4—C5—C6—N1	0.5 (7)	S1—C7—C8—C9	175.4 (3)
C6'—N1'—C2'—C3'	−49.9 (4)	C7—C8—C9—C10	1.1 (5)
S1—N1'—C2'—C3'	109.8 (3)	C8—C9—C10—C11	0.3 (5)
C6'—N1'—C2'—C3	76.3 (3)	C8—C9—C10—Cl1	−178.3 (3)
S1—N1'—C2'—C3	−124.0 (2)	C9—C10—C11—C12	−1.1 (5)
C4—C3—C2'—N1'	34.0 (4)	Cl1—C10—C11—C12	177.4 (3)
C2—C3—C2'—N1'	−149.0 (3)	C8—C7—C12—C11	0.8 (5)
C4—C3—C2'—C3'	157.0 (3)	S1—C7—C12—C11	−176.2 (2)
C2—C3—C2'—C3'	−26.0 (4)	C10—C11—C12—C7	0.6 (5)
N1'—C2'—C3'—C4'	52.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.58	3.383 (4)	145
C3′—H3′B···Cl1ⁱⁱ	0.97	2.98	3.923 (4)	163
C8—H8···Cl1ⁱⁱⁱ	0.93	2.97	3.807 (3)	150
C2′—H2′A···O1	0.98	2.38	2.880 (4)	111

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2.

(S)-3-[1-(4-Methylphenyl)piperidin-2-yl]pyridine (2) top

Crystal data top

C₁₇H₂₀N₂O₂S	D_x = 1.283 Mg m⁻³
M_r = 316.41	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 7339 reflections
a = 7.8933 (16) Å	θ = 4.6–75.5°
b = 11.408 (2) Å	µ = 1.82 mm⁻¹
c = 18.195 (4) Å	T = 297 K
V = 1638.5 (6) Å³	Prism, colourless
Z = 4	0.45 × 0.30 × 0.25 mm
F(000) = 672

Data collection top

Xcalibur, Ruby diffractometer	3372 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3194 reflections with I > 2σ(I)
Detector resolution: 10.25 pixels mm^-1	R_int = 0.033
ω scans	θ_max = 76.1°, θ_min = 4.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −6→9
T_min = 0.79, T_max = 1.00	k = −13→14
11987 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0837P)² + 0.0529P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
3372 reflections	Δρ_max = 0.33 e Å⁻³
200 parameters	Δρ_min = −0.63 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1275 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.005 (8)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.55288 (8)	0.37284 (6)	0.27853 (4)	0.0502 (2)
O1	0.4044 (3)	0.3086 (3)	0.29892 (14)	0.0721 (7)
O2	0.5731 (4)	0.4921 (2)	0.30207 (14)	0.0760 (7)
N1	0.8626 (7)	−0.0151 (4)	0.4744 (2)	0.1120 (15)
N1'	0.7130 (3)	0.30057 (18)	0.31083 (13)	0.0457 (5)
C2	0.8256 (7)	0.0261 (4)	0.4078 (2)	0.0849 (12)
H2	0.852141	−0.021362	0.367817	0.102*
C3	0.7515 (3)	0.1328 (3)	0.39290 (15)	0.0527 (6)
C4	0.7098 (6)	0.2002 (4)	0.4530 (2)	0.0784 (10)
H4	0.657245	0.272468	0.446699	0.094*
C5	0.7469 (7)	0.1593 (5)	0.5232 (2)	0.0969 (15)
H5	0.719813	0.203753	0.564383	0.116*
C6	0.8237 (7)	0.0529 (5)	0.5304 (3)	0.1011 (16)
H6	0.850092	0.026908	0.577437	0.121*
C2'	0.7089 (3)	0.1711 (2)	0.31480 (15)	0.0453 (5)
H2'A	0.592381	0.146268	0.304605	0.054*
C3'	0.8224 (4)	0.1185 (2)	0.25495 (17)	0.0606 (7)
H3'A	0.827492	0.034133	0.261322	0.073*
H3'B	0.772751	0.134164	0.207184	0.073*
C4'	1.0008 (4)	0.1681 (3)	0.2570 (2)	0.0681 (8)
H4'A	1.054458	0.147950	0.303297	0.082*
H4'B	1.067557	0.134495	0.217513	0.082*
C5'	0.9938 (4)	0.3002 (3)	0.2487 (2)	0.0693 (9)
H5'A	1.107324	0.332288	0.251852	0.083*
H5'B	0.947808	0.320006	0.200815	0.083*
C6'	0.8839 (4)	0.3532 (2)	0.3083 (2)	0.0596 (7)
H6'A	0.938763	0.342307	0.355476	0.072*
H6'B	0.873433	0.436851	0.299725	0.072*
C7	0.5649 (3)	0.3733 (2)	0.18179 (14)	0.0481 (5)
C8	0.6399 (4)	0.4666 (3)	0.1460 (2)	0.0626 (7)
H8	0.681949	0.529831	0.172646	0.075*
C9	0.6520 (6)	0.4652 (4)	0.0700 (2)	0.0819 (11)
H9	0.703039	0.527751	0.045869	0.098*
C10	0.5884 (5)	0.3708 (4)	0.02895 (19)	0.0784 (10)
C11	0.5151 (6)	0.2779 (4)	0.0668 (2)	0.0793 (11)
H11	0.473604	0.213963	0.040632	0.095*
C12	0.5027 (5)	0.2787 (3)	0.14224 (18)	0.0625 (7)
H12	0.452790	0.215910	0.166656	0.075*
C13	0.5936 (8)	0.3691 (6)	−0.0544 (2)	0.127 (2)
H13A	0.667796	0.429881	−0.071637	0.190*
H13B	0.481636	0.382083	−0.073425	0.190*
H13C	0.634474	0.294420	−0.070964	0.190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0479 (3)	0.0526 (3)	0.0501 (3)	0.0144 (3)	−0.0047 (2)	−0.0035 (3)
O1	0.0437 (10)	0.1059 (19)	0.0667 (13)	0.0080 (11)	0.0036 (9)	0.0118 (12)
O2	0.0981 (18)	0.0566 (12)	0.0733 (13)	0.0353 (13)	−0.0174 (13)	−0.0188 (10)
N1	0.149 (4)	0.102 (3)	0.085 (3)	0.018 (3)	−0.024 (3)	0.037 (2)
N1'	0.0442 (10)	0.0379 (10)	0.0550 (11)	0.0017 (8)	−0.0103 (9)	−0.0008 (9)
C2	0.117 (3)	0.067 (2)	0.070 (2)	0.016 (2)	−0.006 (2)	0.0198 (18)
C3	0.0557 (14)	0.0492 (14)	0.0533 (13)	−0.0067 (11)	−0.0059 (11)	0.0056 (12)
C4	0.099 (3)	0.080 (2)	0.0566 (18)	0.004 (2)	−0.0004 (18)	0.0021 (17)
C5	0.120 (4)	0.117 (4)	0.0541 (19)	−0.014 (3)	0.002 (2)	−0.003 (2)
C6	0.115 (4)	0.118 (4)	0.070 (3)	−0.024 (3)	−0.027 (2)	0.036 (3)
C2'	0.0486 (12)	0.0361 (11)	0.0512 (13)	−0.0043 (9)	−0.0080 (10)	0.0012 (10)
C3'	0.0848 (19)	0.0404 (12)	0.0565 (14)	0.0077 (13)	−0.0022 (14)	−0.0022 (12)
C4'	0.0637 (16)	0.0616 (16)	0.079 (2)	0.0210 (14)	0.0109 (15)	0.0129 (15)
C5'	0.0460 (13)	0.0626 (17)	0.099 (2)	0.0015 (12)	0.0014 (14)	0.0232 (17)
C6'	0.0530 (14)	0.0388 (12)	0.087 (2)	−0.0075 (11)	−0.0178 (14)	0.0043 (12)
C7	0.0443 (12)	0.0464 (12)	0.0536 (13)	0.0084 (11)	−0.0065 (10)	0.0012 (11)
C8	0.0639 (17)	0.0525 (15)	0.0714 (18)	−0.0007 (13)	−0.0036 (15)	0.0082 (14)
C9	0.082 (2)	0.087 (3)	0.077 (2)	0.011 (2)	0.0118 (19)	0.030 (2)
C10	0.087 (2)	0.094 (3)	0.0540 (16)	0.029 (2)	0.0010 (15)	0.0079 (18)
C11	0.101 (3)	0.075 (2)	0.0610 (18)	0.013 (2)	−0.0191 (18)	−0.0132 (17)
C12	0.0765 (19)	0.0513 (14)	0.0596 (16)	−0.0014 (14)	−0.0153 (14)	0.0005 (13)
C13	0.146 (5)	0.179 (6)	0.056 (2)	0.054 (5)	0.010 (3)	0.012 (3)

Geometric parameters (Å, º) top

S1—O1	1.431 (2)	C4'—C5'	1.516 (4)
S1—O2	1.436 (2)	C4'—H4'A	0.9700
S1—N1'	1.620 (2)	C4'—H4'B	0.9700
S1—C7	1.763 (3)	C5'—C6'	1.515 (5)
N1—C6	1.316 (7)	C5'—H5'A	0.9700
N1—C2	1.333 (5)	C5'—H5'B	0.9700
N1'—C6'	1.477 (3)	C6'—H6'A	0.9700
N1'—C2'	1.479 (3)	C6'—H6'B	0.9700
C2—C3	1.378 (5)	C7—C8	1.381 (4)
C2—H2	0.9300	C7—C12	1.387 (4)
C3—C4	1.376 (5)	C8—C9	1.386 (6)
C3—C2'	1.524 (4)	C8—H8	0.9300
C4—C5	1.390 (6)	C9—C10	1.404 (6)
C4—H4	0.9300	C9—H9	0.9300
C5—C6	1.364 (8)	C10—C11	1.391 (6)
C5—H5	0.9300	C10—C13	1.518 (5)
C6—H6	0.9300	C11—C12	1.376 (5)
C2'—C3'	1.533 (4)	C11—H11	0.9300
C2'—H2'A	0.9800	C12—H12	0.9300
C3'—C4'	1.518 (5)	C13—H13A	0.9600
C3'—H3'A	0.9700	C13—H13B	0.9600
C3'—H3'B	0.9700	C13—H13C	0.9600

O1—S1—O2	119.94 (17)	C5'—C4'—H4'B	109.8
O1—S1—N1'	106.52 (13)	C3'—C4'—H4'B	109.8
O2—S1—N1'	106.71 (13)	H4'A—C4'—H4'B	108.2
O1—S1—C7	107.73 (14)	C6'—C5'—C4'	110.3 (3)
O2—S1—C7	106.80 (15)	C6'—C5'—H5'A	109.6
N1'—S1—C7	108.78 (12)	C4'—C5'—H5'A	109.6
C6—N1—C2	116.4 (4)	C6'—C5'—H5'B	109.6
C6'—N1'—C2'	115.3 (2)	C4'—C5'—H5'B	109.6
C6'—N1'—S1	119.61 (18)	H5'A—C5'—H5'B	108.1
C2'—N1'—S1	120.58 (18)	N1'—C6'—C5'	112.5 (2)
N1—C2—C3	125.7 (4)	N1'—C6'—H6'A	109.1
N1—C2—H2	117.2	C5'—C6'—H6'A	109.1
C3—C2—H2	117.2	N1'—C6'—H6'B	109.1
C4—C3—C2	116.1 (3)	C5'—C6'—H6'B	109.1
C4—C3—C2'	121.8 (3)	H6'A—C6'—H6'B	107.8
C2—C3—C2'	122.0 (3)	C8—C7—C12	120.5 (3)
C3—C4—C5	119.5 (4)	C8—C7—S1	119.7 (2)
C3—C4—H4	120.3	C12—C7—S1	119.8 (2)
C5—C4—H4	120.3	C7—C8—C9	119.4 (3)
C6—C5—C4	118.7 (4)	C7—C8—H8	120.3
C6—C5—H5	120.6	C9—C8—H8	120.3
C4—C5—H5	120.6	C8—C9—C10	121.0 (4)
N1—C6—C5	123.7 (4)	C8—C9—H9	119.5
N1—C6—H6	118.2	C10—C9—H9	119.5
C5—C6—H6	118.2	C11—C10—C9	118.1 (3)
N1'—C2'—C3	109.1 (2)	C11—C10—C13	119.8 (4)
N1'—C2'—C3'	110.1 (2)	C9—C10—C13	122.2 (4)
C3—C2'—C3'	114.9 (2)	C12—C11—C10	121.2 (4)
N1'—C2'—H2'A	107.5	C12—C11—H11	119.4
C3—C2'—H2'A	107.5	C10—C11—H11	119.4
C3'—C2'—H2'A	107.5	C11—C12—C7	119.8 (3)
C4'—C3'—C2'	112.2 (2)	C11—C12—H12	120.1
C4'—C3'—H3'A	109.2	C7—C12—H12	120.1
C2'—C3'—H3'A	109.2	C10—C13—H13A	109.5
C4'—C3'—H3'B	109.2	C10—C13—H13B	109.5
C2'—C3'—H3'B	109.2	H13A—C13—H13B	109.5
H3'A—C3'—H3'B	107.9	C10—C13—H13C	109.5
C5'—C4'—C3'	109.5 (2)	H13A—C13—H13C	109.5
C5'—C4'—H4'A	109.8	H13B—C13—H13C	109.5
C3'—C4'—H4'A	109.8

O1—S1—N1'—C6'	−171.2 (2)	C3—C2'—C3'—C4'	−70.5 (3)
O2—S1—N1'—C6'	−41.9 (3)	C2'—C3'—C4'—C5'	−57.7 (4)
C7—S1—N1'—C6'	73.0 (2)	C3'—C4'—C5'—C6'	57.1 (4)
O1—S1—N1'—C2'	33.7 (2)	C2'—N1'—C6'—C5'	51.9 (3)
O2—S1—N1'—C2'	162.9 (2)	S1—N1'—C6'—C5'	−104.5 (3)
C7—S1—N1'—C2'	−82.2 (2)	C4'—C5'—C6'—N1'	−54.2 (4)
C6—N1—C2—C3	0.2 (9)	O1—S1—C7—C8	150.1 (2)
N1—C2—C3—C4	−1.5 (7)	O2—S1—C7—C8	20.0 (3)
N1—C2—C3—C2'	−178.1 (4)	N1'—S1—C7—C8	−94.8 (2)
C2—C3—C4—C5	1.3 (6)	O1—S1—C7—C12	−31.5 (3)
C2'—C3—C4—C5	178.0 (4)	O2—S1—C7—C12	−161.6 (2)
C3—C4—C5—C6	−0.1 (7)	N1'—S1—C7—C12	83.6 (2)
C2—N1—C6—C5	1.2 (9)	C12—C7—C8—C9	0.3 (5)
C4—C5—C6—N1	−1.2 (9)	S1—C7—C8—C9	178.7 (3)
C6'—N1'—C2'—C3	76.8 (3)	C7—C8—C9—C10	0.4 (6)
S1—N1'—C2'—C3	−127.1 (2)	C8—C9—C10—C11	−0.9 (6)
C6'—N1'—C2'—C3'	−50.2 (3)	C8—C9—C10—C13	177.5 (4)
S1—N1'—C2'—C3'	106.0 (2)	C9—C10—C11—C12	0.9 (6)
C4—C3—C2'—N1'	31.3 (4)	C13—C10—C11—C12	−177.6 (4)
C2—C3—C2'—N1'	−152.3 (3)	C10—C11—C12—C7	−0.3 (6)
C4—C3—C2'—C3'	155.4 (3)	C8—C7—C12—C11	−0.3 (5)
C2—C3—C2'—C3'	−28.1 (4)	S1—C7—C12—C11	−178.7 (3)
N1'—C2'—C3'—C4'	53.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.62	3.474 (4)	152
C5′—H5′A···O1ⁱⁱ	0.97	2.51	3.369 (4)	147
C2′—H2′A···O1	0.98	2.37	2.884 (4)	112

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

(S)-3-{1-[(4-Methoxyphenyl)sulfonyl]piperidin-2-yl}pyridine (3) top

Crystal data top

C₁₇H₂₀N₂O₃S	D_x = 1.326 Mg m⁻³
M_r = 332.41	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3974 reflections
a = 7.9758 (16) Å	θ = 4.6–75.4°
b = 11.131 (2) Å	µ = 1.87 mm⁻¹
c = 18.754 (4) Å	T = 297 K
V = 1664.9 (6) Å³	Prism, colorless
Z = 4	0.30 × 0.25 × 0.25 mm
F(000) = 704

Data collection top

Xcalibur, Ruby diffractometer	3427 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2899 reflections with I > 2σ(I)
Detector resolution: 10.25 pixels mm^-1	R_int = 0.048
ω scans	θ_max = 76.0°, θ_min = 4.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.78, T_max = 1.00	k = −13→12
12142 measured reflections	l = −16→23

Refinement top

Refinement on F²	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0709P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3427 reflections	Δρ_max = 0.23 e Å⁻³
209 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1030 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: −0.014 (15)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.46400 (12)	0.61342 (10)	0.28240 (5)	0.0586 (3)
O1	0.6090 (3)	0.6847 (4)	0.29802 (18)	0.0831 (10)
O2	0.4573 (5)	0.4897 (3)	0.30408 (18)	0.0914 (12)
O3	0.3669 (6)	0.6134 (4)	−0.02843 (18)	0.0992 (12)
N1	0.1744 (9)	1.0089 (4)	0.4792 (3)	0.1096 (19)
N1'	0.3076 (4)	0.6794 (3)	0.32116 (16)	0.0484 (7)
C2	0.2009 (9)	0.9644 (5)	0.4140 (3)	0.0853 (16)
H2	0.171996	1.012250	0.375206	0.102*
C3	0.2682 (4)	0.8523 (3)	0.39991 (19)	0.0505 (8)
C4	0.3119 (7)	0.7844 (5)	0.4577 (2)	0.0783 (13)
H4	0.360841	0.709297	0.451587	0.094*
C5	0.2817 (9)	0.8299 (6)	0.5265 (3)	0.0959 (19)
H5	0.308423	0.784710	0.566621	0.115*
C6	0.2137 (9)	0.9398 (6)	0.5333 (3)	0.098 (2)
H6	0.193347	0.968466	0.579069	0.118*
C2'	0.2998 (4)	0.8114 (3)	0.32333 (19)	0.0474 (8)
H2'A	0.409873	0.842128	0.308922	0.057*
C3'	0.1712 (6)	0.8573 (4)	0.2696 (2)	0.0635 (10)
H3'A	0.160356	0.943672	0.274506	0.076*
H3'B	0.210472	0.840398	0.221716	0.076*
C4'	0.0021 (5)	0.7995 (5)	0.2804 (3)	0.0758 (13)
H4'A	−0.075740	0.828800	0.244638	0.091*
H4'B	−0.041450	0.820735	0.327007	0.091*
C5'	0.0179 (5)	0.6647 (5)	0.2745 (3)	0.0803 (14)
H5'A	−0.090207	0.627923	0.283817	0.096*
H5'B	0.051468	0.643487	0.226458	0.096*
C6'	0.1448 (5)	0.6170 (4)	0.3267 (3)	0.0680 (11)
H6'A	0.101579	0.626174	0.374716	0.082*
H6'B	0.161359	0.531918	0.318011	0.082*
C7	0.4342 (4)	0.6160 (4)	0.1891 (2)	0.0527 (8)
C8	0.3478 (6)	0.5245 (4)	0.1551 (2)	0.0629 (10)
H8	0.303865	0.461422	0.181689	0.076*
C9	0.3268 (7)	0.5258 (4)	0.0837 (3)	0.0723 (12)
H9	0.269326	0.463568	0.061386	0.087*
C10	0.3910 (6)	0.6203 (4)	0.0433 (2)	0.0707 (11)
C11	0.4770 (7)	0.7131 (4)	0.0767 (2)	0.0754 (13)
H11	0.520194	0.776552	0.050174	0.091*
C12	0.4977 (6)	0.7099 (4)	0.1497 (2)	0.0645 (11)
H12	0.554942	0.771753	0.172491	0.077*
C13	0.4504 (13)	0.6978 (6)	−0.0724 (3)	0.126 (3)
H13A	0.428234	0.679622	−0.121564	0.189*
H13B	0.568898	0.693693	−0.063780	0.189*
H13C	0.410630	0.777137	−0.061717	0.189*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0518 (4)	0.0659 (6)	0.0579 (4)	0.0238 (4)	0.0040 (4)	0.0017 (5)
O1	0.0406 (14)	0.132 (3)	0.076 (2)	0.0124 (16)	−0.0029 (13)	−0.0161 (19)
O2	0.127 (3)	0.068 (2)	0.078 (2)	0.055 (2)	0.016 (2)	0.0145 (16)
O3	0.139 (4)	0.100 (3)	0.0585 (17)	0.005 (3)	−0.005 (2)	−0.005 (2)
N1	0.171 (6)	0.083 (3)	0.074 (3)	0.009 (4)	0.028 (3)	−0.023 (3)
N1'	0.0449 (15)	0.0412 (15)	0.0591 (17)	0.0035 (12)	0.0085 (13)	0.0000 (13)
C2	0.130 (5)	0.060 (3)	0.065 (3)	0.014 (3)	0.015 (3)	−0.010 (2)
C3	0.0511 (18)	0.049 (2)	0.0517 (17)	−0.0082 (15)	0.0032 (14)	−0.0040 (15)
C4	0.095 (3)	0.079 (3)	0.061 (2)	0.008 (3)	−0.012 (2)	−0.003 (2)
C5	0.126 (5)	0.107 (5)	0.055 (2)	−0.014 (4)	−0.014 (3)	0.002 (3)
C6	0.125 (5)	0.099 (4)	0.069 (3)	−0.037 (4)	0.024 (3)	−0.027 (3)
C2'	0.0460 (17)	0.0416 (18)	0.0546 (19)	−0.0007 (14)	0.0090 (14)	−0.0014 (15)
C3'	0.086 (3)	0.052 (2)	0.0524 (19)	0.0177 (19)	0.0015 (18)	0.0036 (16)
C4'	0.058 (2)	0.099 (3)	0.070 (2)	0.030 (2)	−0.011 (2)	−0.022 (3)
C5'	0.0406 (18)	0.092 (3)	0.108 (4)	−0.0055 (19)	0.004 (2)	−0.041 (3)
C6'	0.065 (2)	0.0450 (19)	0.094 (3)	−0.0125 (19)	0.028 (2)	−0.007 (2)
C7	0.052 (2)	0.0500 (19)	0.0566 (17)	0.0104 (16)	0.0106 (14)	−0.0024 (17)
C8	0.062 (2)	0.053 (2)	0.074 (3)	−0.0044 (18)	0.0116 (19)	−0.0008 (19)
C9	0.078 (3)	0.065 (3)	0.074 (3)	−0.010 (2)	0.000 (2)	−0.011 (2)
C10	0.086 (3)	0.068 (3)	0.058 (2)	0.013 (3)	0.004 (2)	−0.007 (2)
C11	0.105 (4)	0.056 (2)	0.066 (2)	−0.003 (2)	0.021 (3)	0.004 (2)
C12	0.081 (3)	0.048 (2)	0.064 (2)	−0.007 (2)	0.013 (2)	−0.0084 (18)
C13	0.215 (9)	0.103 (4)	0.061 (3)	0.023 (5)	0.019 (4)	0.009 (3)

Geometric parameters (Å, º) top

S1—O1	1.433 (4)	C3'—H3'B	0.9700
S1—O2	1.437 (4)	C4'—C5'	1.510 (7)
S1—N1'	1.620 (3)	C4'—H4'A	0.9700
S1—C7	1.765 (4)	C4'—H4'B	0.9700
O3—C10	1.360 (5)	C5'—C6'	1.504 (7)
O3—C13	1.416 (8)	C5'—H5'A	0.9700
N1—C6	1.311 (8)	C5'—H5'B	0.9700
N1—C2	1.337 (6)	C6'—H6'A	0.9700
N1'—C2'	1.471 (4)	C6'—H6'B	0.9700
N1'—C6'	1.477 (5)	C7—C12	1.377 (6)
C2—C3	1.384 (6)	C7—C8	1.386 (6)
C2—H2	0.9300	C8—C9	1.349 (7)
C3—C4	1.365 (6)	C8—H8	0.9300
C3—C2'	1.528 (5)	C9—C10	1.394 (7)
C4—C5	1.408 (7)	C9—H9	0.9300
C4—H4	0.9300	C10—C11	1.389 (7)
C5—C6	1.344 (9)	C11—C12	1.380 (6)
C5—H5	0.9300	C11—H11	0.9300
C6—H6	0.9300	C12—H12	0.9300
C2'—C3'	1.525 (5)	C13—H13A	0.9600
C2'—H2'A	0.9800	C13—H13B	0.9600
C3'—C4'	1.508 (7)	C13—H13C	0.9600
C3'—H3'A	0.9700

O1—S1—O2	120.2 (2)	C5'—C4'—H4'A	109.7
O1—S1—N1'	106.19 (18)	C3'—C4'—H4'B	109.7
O2—S1—N1'	106.21 (19)	C5'—C4'—H4'B	109.7
O1—S1—C7	107.59 (19)	H4'A—C4'—H4'B	108.2
O2—S1—C7	106.9 (2)	C6'—C5'—C4'	111.1 (4)
N1'—S1—C7	109.47 (17)	C6'—C5'—H5'A	109.4
C10—O3—C13	118.1 (5)	C4'—C5'—H5'A	109.4
C6—N1—C2	116.9 (5)	C6'—C5'—H5'B	109.4
C2'—N1'—C6'	115.5 (3)	C4'—C5'—H5'B	109.4
C2'—N1'—S1	119.9 (2)	H5'A—C5'—H5'B	108.0
C6'—N1'—S1	119.7 (3)	N1'—C6'—C5'	112.3 (4)
N1—C2—C3	124.7 (5)	N1'—C6'—H6'A	109.1
N1—C2—H2	117.6	C5'—C6'—H6'A	109.1
C3—C2—H2	117.6	N1'—C6'—H6'B	109.1
C4—C3—C2	116.5 (4)	C5'—C6'—H6'B	109.1
C4—C3—C2'	122.6 (4)	H6'A—C6'—H6'B	107.9
C2—C3—C2'	120.8 (4)	C12—C7—C8	119.5 (4)
C3—C4—C5	119.0 (5)	C12—C7—S1	119.7 (3)
C3—C4—H4	120.5	C8—C7—S1	120.8 (3)
C5—C4—H4	120.5	C9—C8—C7	120.7 (4)
C6—C5—C4	118.9 (6)	C9—C8—H8	119.6
C6—C5—H5	120.5	C7—C8—H8	119.6
C4—C5—H5	120.5	C8—C9—C10	120.1 (4)
N1—C6—C5	123.8 (5)	C8—C9—H9	119.9
N1—C6—H6	118.1	C10—C9—H9	119.9
C5—C6—H6	118.1	O3—C10—C11	123.9 (5)
N1'—C2'—C3'	110.1 (3)	O3—C10—C9	116.3 (5)
N1'—C2'—C3	109.3 (3)	C11—C10—C9	119.8 (4)
C3'—C2'—C3	114.2 (3)	C12—C11—C10	119.2 (4)
N1'—C2'—H2'A	107.7	C12—C11—H11	120.4
C3'—C2'—H2'A	107.7	C10—C11—H11	120.4
C3—C2'—H2'A	107.7	C7—C12—C11	120.6 (4)
C4'—C3'—C2'	111.8 (3)	C7—C12—H12	119.7
C4'—C3'—H3'A	109.3	C11—C12—H12	119.7
C2'—C3'—H3'A	109.3	O3—C13—H13A	109.5
C4'—C3'—H3'B	109.3	O3—C13—H13B	109.5
C2'—C3'—H3'B	109.3	H13A—C13—H13B	109.5
H3'A—C3'—H3'B	107.9	O3—C13—H13C	109.5
C3'—C4'—C5'	109.8 (3)	H13A—C13—H13C	109.5
C3'—C4'—H4'A	109.7	H13B—C13—H13C	109.5

O1—S1—N1'—C2'	37.2 (4)	C2'—C3'—C4'—C5'	−57.7 (5)
O2—S1—N1'—C2'	166.2 (3)	C3'—C4'—C5'—C6'	56.3 (5)
C7—S1—N1'—C2'	−78.7 (3)	C2'—N1'—C6'—C5'	50.9 (5)
O1—S1—N1'—C6'	−168.7 (3)	S1—N1'—C6'—C5'	−104.3 (4)
O2—S1—N1'—C6'	−39.7 (4)	C4'—C5'—C6'—N1'	−52.4 (5)
C7—S1—N1'—C6'	75.4 (3)	O1—S1—C7—C12	−24.0 (4)
C6—N1—C2—C3	−0.9 (11)	O2—S1—C7—C12	−154.3 (3)
N1—C2—C3—C4	−0.9 (9)	N1'—S1—C7—C12	91.0 (3)
N1—C2—C3—C2'	−177.6 (6)	O1—S1—C7—C8	155.9 (3)
C2—C3—C4—C5	1.9 (8)	O2—S1—C7—C8	25.6 (4)
C2'—C3—C4—C5	178.6 (5)	N1'—S1—C7—C8	−89.1 (3)
C3—C4—C5—C6	−1.2 (9)	C12—C7—C8—C9	0.7 (6)
C2—N1—C6—C5	1.7 (11)	S1—C7—C8—C9	−179.2 (4)
C4—C5—C6—N1	−0.6 (11)	C7—C8—C9—C10	−0.5 (8)
C6'—N1'—C2'—C3'	−50.7 (4)	C13—O3—C10—C11	7.6 (8)
S1—N1'—C2'—C3'	104.4 (3)	C13—O3—C10—C9	−171.0 (6)
C6'—N1'—C2'—C3	75.5 (4)	C8—C9—C10—O3	178.8 (5)
S1—N1'—C2'—C3	−129.4 (3)	C8—C9—C10—C11	0.1 (8)
C4—C3—C2'—N1'	25.2 (5)	O3—C10—C11—C12	−178.5 (5)
C2—C3—C2'—N1'	−158.3 (4)	C9—C10—C11—C12	0.1 (8)
C4—C3—C2'—C3'	149.1 (4)	C8—C7—C12—C11	−0.5 (6)
C2—C3—C2'—C3'	−34.4 (6)	S1—C7—C12—C11	179.4 (4)
N1'—C2'—C3'—C4'	54.0 (4)	C10—C11—C12—C7	0.1 (7)
C3—C2'—C3'—C4'	−69.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.47	3.252 (5)	142
C5′—H5′A···O1ⁱⁱ	0.97	2.49	3.298 (5)	140
C2′—H2′A···O1	0.98	2.37	2.880 (5)	111

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z.

(S)-3-{1-[(3,4-Dimethylphenyl)sulfonyl]piperidin-2-yl}pyridine (4) top

Crystal data top

C₁₈H₂₂N₂O₂S	D_x = 1.305 Mg m⁻³
M_r = 330.43	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3960 reflections
a = 7.9087 (16) Å	θ = 3.8–75.1°
b = 11.737 (2) Å	µ = 1.80 mm⁻¹
c = 18.117 (4) Å	T = 295 K
V = 1681.6 (6) Å³	Prism, colourless
Z = 4	0.45 × 0.25 × 0.22 mm
F(000) = 704

Data collection top

Xcalibur, Ruby diffractometer	3428 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2886 reflections with I > 2σ(I)
Detector resolution: 10.25 pixels mm^-1	R_int = 0.045
ω scans	θ_max = 76.2°, θ_min = 4.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.88, T_max = 1.00	k = −14→14
12220 measured reflections	l = −22→16

Refinement top

Refinement on F²	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3428 reflections	Δρ_max = 0.21 e Å⁻³
210 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1007 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.011 (14)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.44287 (11)	0.14787 (7)	0.28526 (4)	0.0513 (2)
O1	0.5899 (3)	0.2085 (3)	0.30954 (14)	0.0713 (8)
O2	0.4152 (4)	0.0330 (2)	0.30906 (14)	0.0738 (8)
N1	0.1338 (6)	0.5418 (3)	0.4672 (2)	0.0802 (11)
N1'	0.2807 (3)	0.2215 (2)	0.31248 (14)	0.0459 (6)
C2	0.1745 (6)	0.4979 (3)	0.4014 (2)	0.0648 (10)
H2	0.157045	0.543351	0.360070	0.078*
C3	0.2404 (4)	0.3903 (3)	0.39001 (17)	0.0471 (7)
C4	0.2700 (6)	0.3259 (3)	0.45187 (19)	0.0660 (10)
H4	0.318057	0.253834	0.447733	0.079*
C5	0.2273 (6)	0.3694 (4)	0.5209 (2)	0.0775 (12)
H5	0.244599	0.326389	0.563353	0.093*
C6	0.1599 (6)	0.4756 (4)	0.5252 (2)	0.0762 (13)
H6	0.130429	0.503421	0.571493	0.091*
C2'	0.2876 (4)	0.3471 (3)	0.31322 (16)	0.0458 (7)
H2'A	0.404956	0.369480	0.303765	0.055*
C3'	0.1791 (6)	0.3954 (3)	0.25051 (18)	0.0601 (9)
H3'A	0.175535	0.477799	0.254520	0.072*
H3'B	0.230610	0.376342	0.203524	0.072*
C4'	0.0008 (5)	0.3491 (4)	0.2525 (2)	0.0687 (10)
H4'B	−0.054026	0.372414	0.297957	0.082*
H4'A	−0.063361	0.379805	0.211468	0.082*
C5'	0.0037 (5)	0.2213 (4)	0.2479 (2)	0.0685 (11)
H5'B	0.050165	0.198218	0.200642	0.082*
H5'A	−0.110794	0.192194	0.251255	0.082*
C6'	0.1102 (5)	0.1715 (3)	0.3099 (2)	0.0585 (9)
H6'A	0.053836	0.184907	0.356662	0.070*
H6'B	0.119525	0.089753	0.303072	0.070*
C7	0.4458 (4)	0.1468 (3)	0.18773 (16)	0.0478 (6)
C8	0.3742 (5)	0.0569 (3)	0.1500 (2)	0.0536 (8)
H8	0.326167	−0.003003	0.176245	0.064*
C9	0.3728 (5)	0.0547 (4)	0.0731 (2)	0.0662 (11)
C10	0.4447 (6)	0.1471 (4)	0.03484 (19)	0.0725 (11)
C11	0.5126 (6)	0.2369 (4)	0.0740 (2)	0.0727 (12)
H11	0.558208	0.298156	0.048268	0.087*
C12	0.5152 (5)	0.2386 (3)	0.1501 (2)	0.0609 (9)
H12	0.562128	0.299646	0.175608	0.073*
C13	0.4524 (9)	0.1493 (6)	−0.0490 (2)	0.117 (2)
H13A	0.465980	0.226429	−0.065598	0.176*
H13B	0.349504	0.118467	−0.068832	0.176*
H13C	0.546474	0.104368	−0.065538	0.176*
C14	0.2982 (7)	−0.0467 (5)	0.0344 (3)	0.1006 (17)
H14A	0.242833	−0.094837	0.069736	0.151*
H14B	0.386563	−0.088725	0.010278	0.151*
H14C	0.217586	−0.021386	−0.001693	0.151*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0538 (4)	0.0543 (4)	0.0457 (3)	0.0128 (4)	−0.0003 (4)	0.0025 (3)
O1	0.0490 (16)	0.103 (2)	0.0614 (14)	0.0111 (14)	−0.0086 (11)	−0.0105 (14)
O2	0.099 (2)	0.0579 (15)	0.0644 (14)	0.0281 (15)	0.0088 (15)	0.0157 (12)
N1	0.099 (3)	0.072 (2)	0.070 (2)	0.005 (2)	0.0139 (19)	−0.0233 (19)
N1'	0.0470 (15)	0.0423 (14)	0.0484 (13)	−0.0004 (12)	0.0055 (11)	−0.0010 (11)
C2	0.083 (3)	0.054 (2)	0.057 (2)	0.0003 (19)	0.0050 (19)	−0.0065 (17)
C3	0.0486 (18)	0.0468 (17)	0.0457 (16)	−0.0090 (13)	0.0018 (14)	−0.0031 (13)
C4	0.086 (3)	0.063 (2)	0.0494 (18)	0.003 (2)	0.0042 (18)	−0.0026 (16)
C5	0.096 (3)	0.091 (3)	0.0453 (18)	−0.005 (3)	0.0028 (19)	−0.005 (2)
C6	0.079 (3)	0.091 (3)	0.059 (2)	−0.014 (2)	0.012 (2)	−0.028 (2)
C2'	0.0528 (18)	0.0396 (15)	0.0449 (13)	−0.0040 (14)	0.0076 (13)	0.0001 (13)
C3'	0.085 (3)	0.0494 (19)	0.0461 (19)	0.0083 (17)	0.0047 (17)	0.0002 (14)
C4'	0.070 (2)	0.076 (3)	0.060 (2)	0.021 (2)	−0.0114 (16)	−0.011 (2)
C5'	0.051 (2)	0.079 (3)	0.076 (2)	−0.0010 (18)	−0.0030 (17)	−0.024 (2)
C6'	0.057 (2)	0.0468 (18)	0.071 (2)	−0.0100 (14)	0.0121 (17)	−0.0071 (15)
C7	0.0470 (16)	0.0500 (16)	0.0463 (13)	0.0116 (17)	0.0035 (13)	−0.0027 (13)
C8	0.0516 (19)	0.0476 (18)	0.0615 (18)	0.0099 (14)	0.0050 (15)	−0.0060 (15)
C9	0.055 (2)	0.079 (3)	0.064 (2)	0.025 (2)	−0.0063 (18)	−0.021 (2)
C10	0.076 (3)	0.094 (3)	0.0475 (16)	0.035 (3)	0.0031 (18)	0.000 (2)
C11	0.083 (3)	0.077 (3)	0.058 (2)	0.016 (2)	0.0150 (19)	0.017 (2)
C12	0.067 (3)	0.056 (2)	0.0602 (19)	0.0046 (17)	0.0099 (17)	0.0030 (17)
C13	0.131 (5)	0.174 (6)	0.046 (2)	0.070 (5)	0.002 (3)	0.002 (3)
C14	0.086 (4)	0.115 (4)	0.100 (3)	0.016 (3)	−0.012 (3)	−0.056 (3)

Geometric parameters (Å, º) top

S1—O1	1.432 (3)	C4'—H4'A	0.9700
S1—O2	1.432 (3)	C5'—C6'	1.521 (6)
S1—N1'	1.623 (3)	C5'—H5'B	0.9700
S1—C7	1.767 (3)	C5'—H5'A	0.9700
N1—C6	1.322 (6)	C6'—H6'A	0.9700
N1—C2	1.339 (5)	C6'—H6'B	0.9700
N1'—C6'	1.472 (4)	C7—C8	1.378 (5)
N1'—C2'	1.475 (4)	C7—C12	1.387 (5)
C2—C3	1.381 (5)	C8—C9	1.394 (5)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.372 (5)	C9—C10	1.407 (6)
C3—C2'	1.527 (4)	C9—C14	1.503 (6)
C4—C5	1.392 (5)	C10—C11	1.379 (7)
C4—H4	0.9300	C10—C13	1.520 (5)
C5—C6	1.359 (7)	C11—C12	1.380 (5)
C5—H5	0.9300	C11—H11	0.9300
C6—H6	0.9300	C12—H12	0.9300
C2'—C3'	1.532 (5)	C13—H13A	0.9600
C2'—H2'A	0.9800	C13—H13B	0.9600
C3'—C4'	1.511 (6)	C13—H13C	0.9600
C3'—H3'A	0.9700	C14—H14A	0.9600
C3'—H3'B	0.9700	C14—H14B	0.9600
C4'—C5'	1.502 (6)	C14—H14C	0.9600
C4'—H4'B	0.9700

O1—S1—O2	119.96 (19)	C4'—C5'—C6'	110.6 (3)
O1—S1—N1'	106.46 (15)	C4'—C5'—H5'B	109.5
O2—S1—N1'	106.79 (17)	C6'—C5'—H5'B	109.5
O1—S1—C7	107.46 (17)	C4'—C5'—H5'A	109.5
O2—S1—C7	107.23 (16)	C6'—C5'—H5'A	109.5
N1'—S1—C7	108.54 (14)	H5'B—C5'—H5'A	108.1
C6—N1—C2	116.3 (4)	N1'—C6'—C5'	112.2 (3)
C6'—N1'—C2'	115.6 (3)	N1'—C6'—H6'A	109.2
C6'—N1'—S1	120.2 (2)	C5'—C6'—H6'A	109.2
C2'—N1'—S1	120.4 (2)	N1'—C6'—H6'B	109.2
N1—C2—C3	125.2 (4)	C5'—C6'—H6'B	109.2
N1—C2—H2	117.4	H6'A—C6'—H6'B	107.9
C3—C2—H2	117.4	C8—C7—C12	120.9 (3)
C4—C3—C2	116.5 (3)	C8—C7—S1	119.7 (3)
C4—C3—C2'	121.3 (3)	C12—C7—S1	119.4 (3)
C2—C3—C2'	122.2 (3)	C7—C8—C9	120.9 (4)
C3—C4—C5	119.3 (4)	C7—C8—H8	119.6
C3—C4—H4	120.3	C9—C8—H8	119.6
C5—C4—H4	120.3	C8—C9—C10	118.4 (4)
C6—C5—C4	118.9 (4)	C8—C9—C14	119.0 (5)
C6—C5—H5	120.6	C10—C9—C14	122.6 (4)
C4—C5—H5	120.6	C11—C10—C9	119.5 (3)
N1—C6—C5	123.7 (4)	C11—C10—C13	119.0 (5)
N1—C6—H6	118.1	C9—C10—C13	121.4 (5)
C5—C6—H6	118.1	C10—C11—C12	122.1 (4)
N1'—C2'—C3	109.4 (2)	C10—C11—H11	119.0
N1'—C2'—C3'	110.0 (3)	C12—C11—H11	119.0
C3—C2'—C3'	114.5 (3)	C11—C12—C7	118.3 (4)
N1'—C2'—H2'A	107.5	C11—C12—H12	120.9
C3—C2'—H2'A	107.5	C7—C12—H12	120.9
C3'—C2'—H2'A	107.5	C10—C13—H13A	109.5
C4'—C3'—C2'	111.8 (3)	C10—C13—H13B	109.5
C4'—C3'—H3'A	109.3	H13A—C13—H13B	109.5
C2'—C3'—H3'A	109.3	C10—C13—H13C	109.5
C4'—C3'—H3'B	109.3	H13A—C13—H13C	109.5
C2'—C3'—H3'B	109.3	H13B—C13—H13C	109.5
H3'A—C3'—H3'B	107.9	C9—C14—H14A	109.5
C5'—C4'—C3'	110.1 (3)	C9—C14—H14B	109.5
C5'—C4'—H4'B	109.6	H14A—C14—H14B	109.5
C3'—C4'—H4'B	109.6	C9—C14—H14C	109.5
C5'—C4'—H4'A	109.6	H14A—C14—H14C	109.5
C3'—C4'—H4'A	109.6	H14B—C14—H14C	109.5
H4'B—C4'—H4'A	108.2

O1—S1—N1'—C6'	−167.4 (3)	C2'—C3'—C4'—C5'	−57.8 (4)
O2—S1—N1'—C6'	−38.2 (3)	C3'—C4'—C5'—C6'	56.9 (4)
C7—S1—N1'—C6'	77.2 (3)	C2'—N1'—C6'—C5'	51.4 (4)
O1—S1—N1'—C2'	35.6 (3)	S1—N1'—C6'—C5'	−106.6 (3)
O2—S1—N1'—C2'	164.9 (2)	C4'—C5'—C6'—N1'	−53.3 (4)
C7—S1—N1'—C2'	−79.8 (3)	O1—S1—C7—C8	150.0 (3)
C6—N1—C2—C3	0.1 (7)	O2—S1—C7—C8	19.8 (3)
N1—C2—C3—C4	−1.9 (7)	N1'—S1—C7—C8	−95.3 (3)
N1—C2—C3—C2'	−178.6 (4)	O1—S1—C7—C12	−32.2 (3)
C2—C3—C4—C5	2.3 (6)	O2—S1—C7—C12	−162.5 (3)
C2'—C3—C4—C5	179.0 (4)	N1'—S1—C7—C12	82.5 (3)
C3—C4—C5—C6	−1.1 (7)	C12—C7—C8—C9	1.4 (5)
C2—N1—C6—C5	1.4 (7)	S1—C7—C8—C9	179.1 (3)
C4—C5—C6—N1	−0.9 (8)	C7—C8—C9—C10	−0.7 (5)
C6'—N1'—C2'—C3	76.0 (4)	C7—C8—C9—C14	178.1 (4)
S1—N1'—C2'—C3	−126.1 (2)	C8—C9—C10—C11	−0.5 (6)
C6'—N1'—C2'—C3'	−50.6 (4)	C14—C9—C10—C11	−179.3 (4)
S1—N1'—C2'—C3'	107.3 (3)	C8—C9—C10—C13	178.3 (4)
C4—C3—C2'—N1'	28.4 (5)	C14—C9—C10—C13	−0.5 (7)
C2—C3—C2'—N1'	−155.1 (3)	C9—C10—C11—C12	1.0 (7)
C4—C3—C2'—C3'	152.5 (4)	C13—C10—C11—C12	−177.7 (4)
C2—C3—C2'—C3'	−31.0 (5)	C10—C11—C12—C7	−0.4 (6)
N1'—C2'—C3'—C4'	53.3 (4)	C8—C7—C12—C11	−0.9 (6)
C3—C2'—C3'—C4'	−70.3 (4)	S1—C7—C12—C11	−178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5′—H5′A···O1ⁱ	0.97	2.60	3.462 (5)	148
C5—H5···O1ⁱⁱ	0.93	2.64	3.384 (5)	138
C2′—H2′A···O1	0.98	2.39	2.892 (4)	111

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+1.

Funding information

This work was supported by the budget for basic research of the Academy of Sciences of the Republic of Uzbekistan.

References

Abdireymov, K. B., Mukhamedov, N. S., Okmanov, R. Y., Ayimbetov, M. J. & Tashkhodjaev, B. (2011). Acta Cryst. E67, o3345–o3346. Web of Science CrossRef IUCr Journals Google Scholar
Amtaghri, S., Slaoui, M. & Eddouks, M. (2025). Cardiovasc. Hematol. Agents Med. Chem. 23, 11–28. CrossRef CAS PubMed Google Scholar
Artyushin, O. I., Vinogradova, N. M., Sharova, E. V., Genkina, G. K. & Brel, V. K. (2016). Heteroat. Chem. 27, 245–252. CrossRef CAS Google Scholar
Bakbardina, O. V., Rakhimzhanova, N. Z., Gazalieva, M. A., Fazylov, S. D. & Baimagambetov, E. Z. (2006). Russ. J. Appl. Chem. 79, 504–505. CrossRef CAS Google Scholar
Bruker (2012). APEX5 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Daly, J. W. (2005). Cell. Mol. Neurobiol. 25, 513–552. CrossRef PubMed CAS Google Scholar
Dewick, P. M. (2009). Medicinal natural products: a biosynthetic approach edited by P. M. Dewick, pp. 311–42. Chichester: John Wiley & Sons, Ltd. Google Scholar
Felpin, F. X., Vo-Thanh, G., Robins, R. J., Villiéras, J. & Lebreton, J. (2000). Synlett 11, 1646–1648. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Ibraev, M. K., Turdybekov, D. M., Takibaeva, A. T., Nurkenov, O. A., Turdybekov, K. M., Gazaliev, A. M. & Adekenov, S. M. (2006). Russ. J. Gen. Chem. 76, 638–640. CrossRef CAS Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Kuete, V. (2014). Toxicological survey of African medicinal plants edited by V. Kuete, pp. 611–633. New York: Elsevier. Google Scholar
Kulakov, I. V. (2010). Chem. Nat. Compd. 46, 68–71. CrossRef CAS Google Scholar
Kulakov, I. V., Nurkenov, O. A., Turdybekov, D. M., Ibragimov, B. T., Talipov, S. A., Zhambekov, Z. M., Ainabaev, A. A. & Turdybekov, K. M. (2009). Chem. Nat. Compd. 45, 209–212. CrossRef CAS Google Scholar
Kulakov, I. V., Nurkenov, O. A., Turdybekov, D. M. & Turdybekov, K. M. (2010). Chem. Nat. Compd. 46, 257–261. CrossRef CAS Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mukusheva, G. K., Zhasymbekova, A. R., Zhumagalieva, Z. Z., Seidakhmetova, R. B., Nurkenov, O. A., Akishina, E. A., Petkevich, S. K., Dikusar, E. A. & Potkin, V. I. (2022). Molecules 27, 7387. CrossRef PubMed Google Scholar
Nurkenov, O. A., Satpaeva, Z. B., Fazylov, S. D., Seilkhanov, T. M., Turdybekov, K. M., Turdybekov, D. M., Akhmetova, S. B., Makhmutova, A. S. & Gazaliev, A. M. (2016). Chem. Nat. Compd. 52, 276–279. CrossRef CAS Google Scholar
Okmanov, R. Y., Abdireymov, K. B., Matchanova, D. R., Olimova, M. I. & Turgunov, K. K. (2022). Acta Cryst. E78, 1271–1276. CrossRef IUCr Journals Google Scholar
Okmanov, R. Y., Olimova, M. I., Karabaeva, S. B., Sapaev, F. A. & Abdireymov, K. B. (2023). Acta Cryst. E79, 313–318. CrossRef IUCr Journals Google Scholar
Olimova, M. I., Khurramov, A. R., Sasmakov, S. A., Bobakulov, K. M., Levkovich, M. G., Azimova, S. S. & Elmuradov, B. Z. (2025). Chem. Nat. Compd. 61, 957–960. CrossRef CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Slyn'ko, N. M., Tatarova, L. E., Shakirov, M. M. & Shul'ts, E. E. (2013). Chem. Nat. Compd. 49, 294–301. CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Ujváry, I. (2010). Hayes' Handbook of Pesticide Toxicology edited by R. Krieger, pp. 119–22. New York:, Academic Press. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wojciechowska-Nowak, M., Boczoń, W., Rychlewska, U. & Warżajtis, B. (2007). J. Mol. Struct. 840, 44–52. CAS Google Scholar

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Volume 82| Part 6| June 2026|

https://doi.org/10.1107/S2056989026004524

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of (S)-3-{1-[(4-chloro­phen­yl)sulfon­yl]piperidin-2-yl}pyridine, (S)-3-[1-(4-methyl­phen­yl)piperidin-2-yl]pyridine, (S)-3-{1-[(4-meth­­oxy­phen­yl)sulfon­yl]piperidin-2-yl}pyridine and (S)-3-{1-[(3,4-di­methyl­phen­yl)sulfon­yl]piperidin-2-yl}pyridine

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

Crystal structures of (S)-3-{1-[(4-chlorophenyl)sulfonyl]piperidin-2-yl}pyridine, (S)-3-[1-(4-methylphenyl)piperidin-2-yl]pyridine, (S)-3-{1-[(4-methoxyphenyl)sulfonyl]piperidin-2-yl}pyridine and (S)-3-{1-[(3,4-dimethylphenyl)sulfonyl]piperidin-2-yl}pyridine

3. Supramolecular features