2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one

Manjula, V.; Venkateswaramoorthi, R.; Dharmaraja, J.; Selvanayagam, S.

doi:10.1107/S241431462000526X

organic compounds

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Volume 5| Part 4| April 2020| x200526

https://doi.org/10.1107/S241431462000526X

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2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one

V. Manjula,^a R. Venkateswaramoorthi,^b J. Dharmaraja ^c ^* and S. Selvanayagam ^d

^aDepartment of Chemistry, Periyar University, Salem 636 011, India, ^bDepartment of Chemistry, PGP College of Arts and Science, Namakkal 637 207, India, ^cDepartment of Chemistry, Anna Government Arts College, Vadachennimalai, Attur 636 121, India, and ^dPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: jagandharma77@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 March 2020; accepted 15 April 2020; online 21 April 2020)

In the title compound, C₂₀H₂₁NO, the dihedral angle between the phenyl ring is 47.5 (1)° and the piperidine ring adopts a chair conformation. In the crystal, molecules are linked by C—H⋯π interactions into dimers with the molecules related by twofold symmetry.

Keywords: crystal structure; piperidine derivative; C—H⋯π interactions.

CCDC reference: 1996936

Structure description

Piperidine derivatives can act as enzyme stabilizers to improve therapeutic enzyme activity in Fabry patient cell lines (Li et al., 2018 ). Some of these derivatives possess antioxidant (Kim et al., 2016 ) and analgesic activities (Jahan et al., 2016 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound (Fig. 1).

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

The piperidine ring adopts a chair conformation and each substituent adopts an equatorial disposition. The dihedral angles between the piperidine ring (all atoms) and the C6–C11 and C15–C20 benzene rings are 70.31 (11) and 79.00 (11)°, respectively. The dihedral angle between the C6–C11 and C15–C20 benzene rings is 47.51 (12)°. In the crystal, a C2—H2⋯Cgⁱ [Cg = is the centroid of the C6–C11 ring; symmetry code: (i) 1 − x, y, $[{1\over 2}]$ − z) interaction occurs with H2A⋯Cg = 2.73 Å and C2—H2A⋯Cg = 148°. This leads to dimers with the molecules related by twofold rotation symmetry (Fig. 2). The N1—H1N grouping points towards the opposite face of the C6–C11 ring but the H1N⋯Cg separation of 3.15 Å is probably too long to be regarded as a bond.

Figure 2
The crystal packing of the title compound viewed along the b-axis direction. The C—H⋯π interactions are shown as dashed lines. For clarity H atoms not involved in these hydrogen bonds have been omitted.

Synthesis and crystallization

A mixture of hexene-2-one (0.05 mol), benzaldehyde (0.1 mol), ammonium acetate (0.05 mol) and ethanol (40 ml) was heated gently and poured into ether (50 ml) and treated with concentrated hydrochloric acid (25 ml). The precipitated hydrochloride was washed with an ethanol–ether mixture. The base was liberated by adding strong ammonia until the hydrochloride dissolved. Dilution with water afforded the free base. The pure compound was was further recrystallized with benzene–petroleum ether to yield the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO
M_r	291.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	16.7588 (4), 23.4597 (5), 8.7769 (2)
β (°)	98.771 (1)
V (Å³)	3410.34 (13)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	28337, 5208, 2586
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.201, 1.03
No. of reflections	5208
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018/3 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 1996936

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431462000526X/hb4345sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462000526X/hb4345Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020).

2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one top

Crystal data top

C₂₀H₂₁NO	F(000) = 1248
M_r = 291.38	D_x = 1.135 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.7588 (4) Å	Cell parameters from 12118 reflections
b = 23.4597 (5) Å	θ = 2.6–25.8°
c = 8.7769 (2) Å	µ = 0.07 mm⁻¹
β = 98.771 (1)°	T = 296 K
V = 3410.34 (13) Å³	Block, colourless
Z = 8	0.24 × 0.21 × 0.19 mm

Data collection top

Bruker SMART APEX CCD diffractometer	R_int = 0.071
Radiation source: fine-focus sealed tube	θ_max = 30.5°, θ_min = 2.5°
ω and φ scans	h = −23→23
28337 measured reflections	k = −24→33
5208 independent reflections	l = −12→12
2586 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.080	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.201	w = 1/[σ²(F_o²) + (0.0736P)² + 2.1792P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5208 reflections	Δρ_max = 0.22 e Å⁻³
203 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint

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.

Refinement. The C-bound H atoms were placed in idealized locations and refined as riding atoms. The N-bound H atom was located in a difference map and refined with a restraint.

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

	x	y	z	U_iso*/U_eq
H1N	0.1365 (10)	0.3964 (7)	0.4008 (13)	0.034 (5)*
O1	0.20727 (10)	0.25243 (7)	0.7596 (2)	0.0756 (5)
N1	0.14621 (9)	0.38387 (7)	0.4932 (2)	0.0440 (4)
C1	0.08589 (11)	0.34078 (9)	0.5144 (2)	0.0454 (5)
H1	0.091163	0.308720	0.445077	0.054*
C2	0.10339 (12)	0.31960 (10)	0.6811 (3)	0.0537 (5)
H2A	0.093153	0.349981	0.750586	0.064*
H2B	0.067787	0.288036	0.694966	0.064*
C3	0.18939 (13)	0.30065 (10)	0.7189 (2)	0.0520 (5)
C4	0.25116 (12)	0.34443 (9)	0.6888 (2)	0.0475 (5)
H4	0.244557	0.378105	0.751803	0.057*
C5	0.22884 (11)	0.36147 (9)	0.5167 (2)	0.0437 (5)
H5	0.230394	0.327262	0.453108	0.052*
C6	0.00096 (11)	0.36388 (9)	0.4799 (2)	0.0457 (5)
C7	−0.01719 (13)	0.41865 (10)	0.5187 (3)	0.0700 (7)
H7	0.023993	0.443022	0.561372	0.084*
C8	−0.09651 (15)	0.43787 (11)	0.4947 (4)	0.0828 (9)
H8	−0.108226	0.474984	0.521265	0.099*
C9	−0.15798 (13)	0.40190 (12)	0.4315 (3)	0.0697 (7)
H9	−0.210973	0.414956	0.413381	0.084*
C10	−0.14082 (13)	0.34762 (12)	0.3960 (3)	0.0604 (6)
H10	−0.182316	0.323007	0.356199	0.072*
C11	−0.06178 (12)	0.32856 (10)	0.4187 (2)	0.0516 (5)
H11	−0.050688	0.291315	0.392277	0.062*
C12	0.33802 (13)	0.32300 (11)	0.7319 (3)	0.0639 (6)
H12A	0.342670	0.286037	0.684469	0.077*
H12B	0.374059	0.349014	0.689870	0.077*
C13	0.36444 (17)	0.31778 (12)	0.9013 (3)	0.0778 (8)
H13	0.330510	0.298403	0.958095	0.093*
C14	0.4310 (2)	0.33817 (16)	0.9754 (5)	0.1174 (13)
H14A	0.466503	0.357808	0.922576	0.141*
H14B	0.443395	0.333178	1.081520	0.141*
C15	0.28595 (11)	0.40515 (9)	0.4675 (2)	0.0456 (5)
C16	0.34151 (12)	0.38922 (11)	0.3724 (3)	0.0612 (6)
H16	0.342811	0.351815	0.337808	0.073*
C17	0.39434 (14)	0.42874 (14)	0.3297 (3)	0.0784 (8)
H17	0.431583	0.417627	0.267007	0.094*
C18	0.39317 (15)	0.48407 (15)	0.3776 (3)	0.0789 (8)
H18	0.429663	0.510311	0.348618	0.095*
C19	0.33762 (16)	0.50067 (12)	0.4689 (3)	0.0748 (7)
H19	0.335531	0.538466	0.500032	0.090*
C20	0.28487 (13)	0.46112 (10)	0.5145 (3)	0.0609 (6)
H20	0.248064	0.472486	0.577783	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0690 (11)	0.0525 (11)	0.1045 (14)	0.0095 (8)	0.0110 (9)	0.0197 (10)
N1	0.0348 (8)	0.0518 (11)	0.0463 (10)	−0.0014 (7)	0.0090 (7)	0.0037 (8)
C1	0.0413 (10)	0.0423 (12)	0.0544 (12)	−0.0013 (8)	0.0133 (9)	−0.0044 (9)
C2	0.0476 (12)	0.0546 (13)	0.0624 (14)	0.0022 (10)	0.0193 (10)	0.0084 (11)
C3	0.0529 (12)	0.0532 (14)	0.0512 (12)	0.0091 (10)	0.0125 (9)	0.0024 (10)
C4	0.0439 (11)	0.0518 (12)	0.0478 (11)	0.0071 (9)	0.0098 (9)	−0.0018 (9)
C5	0.0374 (10)	0.0478 (12)	0.0479 (11)	0.0005 (8)	0.0128 (8)	−0.0060 (9)
C6	0.0385 (10)	0.0456 (12)	0.0544 (12)	−0.0045 (8)	0.0119 (9)	0.0031 (9)
C7	0.0404 (12)	0.0480 (14)	0.122 (2)	−0.0064 (10)	0.0126 (12)	−0.0035 (14)
C8	0.0521 (14)	0.0491 (15)	0.148 (3)	0.0066 (11)	0.0168 (15)	0.0025 (16)
C9	0.0395 (12)	0.0760 (18)	0.0925 (19)	0.0035 (11)	0.0060 (12)	0.0143 (14)
C10	0.0430 (12)	0.0775 (18)	0.0586 (14)	−0.0155 (11)	0.0011 (10)	0.0021 (12)
C11	0.0498 (12)	0.0539 (13)	0.0513 (12)	−0.0096 (10)	0.0079 (9)	−0.0038 (10)
C12	0.0488 (13)	0.0726 (16)	0.0698 (16)	0.0117 (11)	0.0069 (11)	0.0055 (12)
C13	0.0720 (17)	0.0709 (18)	0.0851 (19)	0.0158 (14)	−0.0048 (14)	−0.0004 (14)
C14	0.105 (3)	0.120 (3)	0.113 (3)	0.007 (2)	−0.029 (2)	−0.028 (2)
C15	0.0353 (10)	0.0602 (14)	0.0413 (10)	0.0017 (9)	0.0059 (8)	−0.0004 (9)
C16	0.0417 (12)	0.0793 (17)	0.0663 (14)	0.0030 (11)	0.0197 (10)	−0.0045 (12)
C17	0.0470 (13)	0.108 (2)	0.0869 (19)	−0.0006 (14)	0.0309 (13)	0.0039 (17)
C18	0.0528 (14)	0.103 (2)	0.0825 (18)	−0.0246 (15)	0.0156 (13)	0.0143 (17)
C19	0.0742 (17)	0.0693 (18)	0.0820 (18)	−0.0205 (13)	0.0160 (14)	−0.0002 (14)
C20	0.0563 (13)	0.0646 (16)	0.0657 (15)	−0.0075 (11)	0.0221 (11)	−0.0078 (12)

Geometric parameters (Å, º) top

O1—C3	1.210 (3)	C9—H9	0.9300
N1—C1	1.461 (2)	C10—C11	1.383 (3)
N1—C5	1.466 (2)	C10—H10	0.9300
N1—H1N	0.854 (9)	C11—H11	0.9300
C1—C6	1.510 (3)	C12—C13	1.491 (4)
C1—C2	1.531 (3)	C12—H12A	0.9700
C1—H1	0.9800	C12—H12B	0.9700
C2—C3	1.496 (3)	C13—C14	1.295 (4)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—H14A	0.9300
C3—C4	1.510 (3)	C14—H14B	0.9300
C4—C12	1.532 (3)	C15—C20	1.377 (3)
C4—C5	1.552 (3)	C15—C16	1.393 (3)
C4—H4	0.9800	C16—C17	1.373 (4)
C5—C15	1.509 (3)	C16—H16	0.9300
C5—H5	0.9800	C17—C18	1.365 (4)
C6—C7	1.375 (3)	C17—H17	0.9300
C6—C11	1.381 (3)	C18—C19	1.374 (4)
C7—C8	1.389 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.382 (3)
C8—C9	1.381 (4)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.352 (3)

C1—N1—C5	113.02 (16)	C10—C9—C8	119.8 (2)
C1—N1—H1N	108.8 (12)	C10—C9—H9	120.1
C5—N1—H1N	107.2 (12)	C8—C9—H9	120.1
N1—C1—C6	112.05 (16)	C9—C10—C11	120.2 (2)
N1—C1—C2	108.11 (16)	C9—C10—H10	119.9
C6—C1—C2	110.23 (16)	C11—C10—H10	119.9
N1—C1—H1	108.8	C6—C11—C10	121.2 (2)
C6—C1—H1	108.8	C6—C11—H11	119.4
C2—C1—H1	108.8	C10—C11—H11	119.4
C3—C2—C1	110.24 (16)	C13—C12—C4	113.5 (2)
C3—C2—H2A	109.6	C13—C12—H12A	108.9
C1—C2—H2A	109.6	C4—C12—H12A	108.9
C3—C2—H2B	109.6	C13—C12—H12B	108.9
C1—C2—H2B	109.6	C4—C12—H12B	108.9
H2A—C2—H2B	108.1	H12A—C12—H12B	107.7
O1—C3—C2	122.0 (2)	C14—C13—C12	125.0 (3)
O1—C3—C4	122.82 (19)	C14—C13—H13	117.5
C2—C3—C4	114.97 (18)	C12—C13—H13	117.5
C3—C4—C12	112.63 (19)	C13—C14—H14A	120.0
C3—C4—C5	105.99 (17)	C13—C14—H14B	120.0
C12—C4—C5	113.78 (16)	H14A—C14—H14B	120.0
C3—C4—H4	108.1	C20—C15—C16	118.4 (2)
C12—C4—H4	108.1	C20—C15—C5	121.60 (18)
C5—C4—H4	108.1	C16—C15—C5	120.0 (2)
N1—C5—C15	110.06 (16)	C17—C16—C15	120.0 (2)
N1—C5—C4	108.14 (14)	C17—C16—H16	120.0
C15—C5—C4	112.57 (16)	C15—C16—H16	120.0
N1—C5—H5	108.7	C18—C17—C16	121.2 (2)
C15—C5—H5	108.7	C18—C17—H17	119.4
C4—C5—H5	108.7	C16—C17—H17	119.4
C7—C6—C11	118.21 (19)	C17—C18—C19	119.5 (2)
C7—C6—C1	121.52 (18)	C17—C18—H18	120.3
C11—C6—C1	120.08 (19)	C19—C18—H18	120.3
C6—C7—C8	120.6 (2)	C18—C19—C20	119.9 (3)
C6—C7—H7	119.7	C18—C19—H19	120.0
C8—C7—H7	119.7	C20—C19—H19	120.0
C9—C8—C7	120.0 (2)	C15—C20—C19	121.0 (2)
C9—C8—H8	120.0	C15—C20—H20	119.5
C7—C8—H8	120.0	C19—C20—H20	119.5

C5—N1—C1—C6	−176.38 (16)	C6—C7—C8—C9	0.0 (5)
C5—N1—C1—C2	61.9 (2)	C7—C8—C9—C10	1.3 (4)
N1—C1—C2—C3	−53.1 (2)	C8—C9—C10—C11	−1.9 (4)
C6—C1—C2—C3	−175.88 (17)	C7—C6—C11—C10	0.4 (3)
C1—C2—C3—O1	−120.6 (2)	C1—C6—C11—C10	175.5 (2)
C1—C2—C3—C4	54.2 (2)	C9—C10—C11—C6	1.0 (3)
O1—C3—C4—C12	−6.1 (3)	C3—C4—C12—C13	−70.9 (3)
C2—C3—C4—C12	179.14 (18)	C5—C4—C12—C13	168.4 (2)
O1—C3—C4—C5	118.9 (2)	C4—C12—C13—C14	−130.5 (3)
C2—C3—C4—C5	−55.8 (2)	N1—C5—C15—C20	48.1 (2)
C1—N1—C5—C15	170.62 (16)	C4—C5—C15—C20	−72.7 (2)
C1—N1—C5—C4	−66.1 (2)	N1—C5—C15—C16	−131.9 (2)
C3—C4—C5—N1	58.6 (2)	C4—C5—C15—C16	107.4 (2)
C12—C4—C5—N1	−177.06 (18)	C20—C15—C16—C17	1.1 (3)
C3—C4—C5—C15	−179.56 (16)	C5—C15—C16—C17	−179.0 (2)
C12—C4—C5—C15	−55.3 (2)	C15—C16—C17—C18	−0.7 (4)
N1—C1—C6—C7	−37.4 (3)	C16—C17—C18—C19	−0.6 (4)
C2—C1—C6—C7	83.0 (3)	C17—C18—C19—C20	1.5 (4)
N1—C1—C6—C11	147.64 (19)	C16—C15—C20—C19	−0.2 (3)
C2—C1—C6—C11	−91.9 (2)	C5—C15—C20—C19	179.8 (2)
C11—C6—C7—C8	−0.9 (4)	C18—C19—C20—C15	−1.1 (4)
C1—C6—C7—C8	−175.9 (2)

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,6-Di­phenyl-3-(prop-2-en-1-yl)piperidin-4-one

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one