Crystal structure of 3-methyl-2,6-bis­(4-methyl-1,3-thia­zol-5-yl)piperidin-4-one

Manimaran, A.; Sethusankar, K.; Ganesan, S.; Ananthan, S.

doi:10.1107/S1600536814018856

organic compounds

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Volume 70| Part 9| September 2014| Page o1055

doi:10.1107/S1600536814018856

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Crystal structure of 3-methyl-2,6-bis(4-methyl-1,3-thiazol-5-yl)piperidin-4-one

A. Manimaran,^a K. Sethusankar,^b ^* S. Ganesan ^a and S. Ananthan ^c

^aOrchid Chemicals & Pharmaceuticals Linmited, Research & Developement Centre, Sozhanganallur, Chennai 600 119, India, ^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Chemistry, Presidency College (Autonomous), Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 August 2014; accepted 20 August 2014; online 30 August 2014)

In the title compound, C₁₄H₁₇N₃OS₂, the central piperidinone ring adopts a chair conformation and the thiazole rings are inclined to its mean plane by 80.16 (12) and 67.15 (12)°. The O atom and methyl group C atom deviate significantly from the mean plane of the central piperidinone ring, by 0.8138 (2) and 0.3175 (2) Å, respectively. The dihedral angle between the thiazole rings is 51.88 (13)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag C(10) chains running parallel to [001].

Keywords: crystal structure; thiazole; piperidine; zigzag chains.

CCDC reference: 1020191

1. Related literature

For biological and pharmaceutical applications of piperidinones and thiazoles, see: Ganellin & Spickett (1965 ). For the synthesis of substituted piperidin-4-ones and their derivatives, see: Noller & Baliah (1948 ). For related structures, see: Gayathri et al. (2008 ); Nithya et al. (2009 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₇N₃OS₂
M_r = 307.43
Orthorhombic, P b c a
a = 11.389 (5) Å
b = 12.660 (5) Å
c = 21.667 (5) Å
V = 3124 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.903, T_max = 0.934
19116 measured reflections
3762 independent reflections
2539 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.150
S = 1.00
3762 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N2ⁱ	0.93	2.49	3.365 (4)	157
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1020191

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814018856/su2768sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018856/su2768Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018856/su2768Isup3.cml

checkCIF report

Related literature top

For biological and pharmaceutical applications of piperidinones and thiazoles, see: Ganellin & Spickett (1965). For the synthesis of substituted piperidin-4-ones and their derivatives, see: Noller & Baliah (1948). For related structures, see: Gayathri et al. (2008); Nithya et al. (2009).

Experimental top

4-methyl-5-formyl thiazole (0.20 mol), 2-butanone (0.10 mol) and ammonium acetate (0.10 mol) were dissolved in 80 ml of distilled ethanol and heated over a boiling water bath with stirring for 8–10 h. Hydrochloric acid in isopropyl alcohol was added and the compound was filtered off as the hydrochloride salt under a nitrogen atmosphere. The compound was neutralized and extracted with dichloromethane. The dichloromethane layer was concentrated and crystals of the title compound were obtained by slow evaporation of a solution in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecular, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines; see Table 1 for details.

3-Methyl-2,6-bis(4-methyl-1,3-thiazol-5-yl)piperidin-4-one top

Crystal data top

C₁₄H₁₇N₃OS₂	F(000) = 1296
M_r = 307.43	D_x = 1.307 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2539 reflections
a = 11.389 (5) Å	θ = 2.6–28.4°
b = 12.660 (5) Å	µ = 0.34 mm⁻¹
c = 21.667 (5) Å	T = 296 K
V = 3124 (2) Å³	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3762 independent reflections
Radiation source: fine-focus sealed tube	2539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.903, T_max = 0.934	k = −16→14
19116 measured reflections	l = −27→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.073P)² + 1.5978P] where P = (F_o² + 2F_c²)/3
3762 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₄H₁₇N₃OS₂	V = 3124 (2) Å³
M_r = 307.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.389 (5) Å	µ = 0.34 mm⁻¹
b = 12.660 (5) Å	T = 296 K
c = 21.667 (5) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3762 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2539 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.934	R_int = 0.034
19116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.00	Δρ_max = 0.52 e Å⁻³
3762 reflections	Δρ_min = −0.47 e Å⁻³
184 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.2579 (2)	−0.01628 (17)	0.49282 (10)	0.0398 (5)
H1	0.3299	−0.0482	0.4765	0.048*
C2	0.1630 (2)	−0.10230 (18)	0.49779 (11)	0.0494 (6)
H2A	0.1914	−0.1595	0.5235	0.059*
H2B	0.0933	−0.0730	0.5170	0.059*
C3	0.1325 (2)	−0.14405 (17)	0.43518 (11)	0.0447 (5)
C4	0.1030 (2)	−0.06171 (17)	0.38720 (11)	0.0423 (5)
H4	0.0300	−0.0275	0.4003	0.051*
C5	0.19957 (19)	0.02385 (17)	0.38724 (10)	0.0393 (5)
H5	0.2730	−0.0079	0.3727	0.047*
C6	0.1691 (2)	0.11454 (18)	0.34598 (11)	0.0435 (5)
C7	0.2132 (2)	0.1418 (2)	0.29028 (11)	0.0514 (6)
C8	0.0832 (3)	0.2696 (2)	0.29990 (14)	0.0647 (8)
H8	0.0403	0.3295	0.2895	0.078*
C9	0.2859 (3)	0.1374 (3)	0.64598 (14)	0.0684 (8)
H9	0.2725	0.1849	0.6780	0.082*
C10	0.3678 (2)	0.0071 (2)	0.59575 (11)	0.0492 (6)
C11	0.2849 (2)	0.03318 (17)	0.55366 (10)	0.0404 (5)
C12	0.4537 (3)	−0.0816 (3)	0.59110 (16)	0.0757 (9)
H12A	0.4317	−0.1368	0.6192	0.114*
H12B	0.5307	−0.0564	0.6014	0.114*
H12C	0.4538	−0.1087	0.5497	0.114*
C13	0.3096 (3)	0.0875 (3)	0.25606 (15)	0.0752 (9)
H13A	0.3797	0.1294	0.2583	0.113*
H13B	0.2871	0.0787	0.2137	0.113*
H13C	0.3239	0.0196	0.2742	0.113*
C14	0.0807 (3)	−0.1090 (2)	0.32444 (12)	0.0630 (7)
H14A	0.1513	−0.1420	0.3096	0.095*
H14B	0.0573	−0.0544	0.2963	0.095*
H14C	0.0195	−0.1609	0.3274	0.095*
N1	0.21742 (16)	0.06327 (14)	0.44979 (8)	0.0402 (4)
H1A	0.2050	0.1279	0.4602	0.048*
N2	0.1627 (2)	0.2306 (2)	0.26420 (11)	0.0649 (6)
N3	0.3680 (2)	0.0677 (2)	0.64846 (10)	0.0656 (6)
O1	0.13353 (18)	−0.23686 (14)	0.42350 (9)	0.0653 (5)
S1	0.20268 (6)	0.13746 (6)	0.58011 (3)	0.0607 (2)
S2	0.06218 (6)	0.20349 (6)	0.36761 (3)	0.0582 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0485 (12)	0.0321 (11)	0.0387 (12)	0.0025 (9)	−0.0018 (9)	−0.0007 (9)
C2	0.0679 (15)	0.0339 (11)	0.0464 (14)	−0.0065 (11)	−0.0023 (11)	0.0072 (10)
C3	0.0467 (12)	0.0337 (12)	0.0537 (14)	−0.0044 (9)	0.0014 (10)	−0.0022 (10)
C4	0.0451 (11)	0.0376 (11)	0.0443 (13)	−0.0024 (9)	−0.0015 (10)	−0.0042 (9)
C5	0.0441 (11)	0.0364 (11)	0.0375 (12)	−0.0004 (9)	−0.0007 (9)	−0.0003 (9)
C6	0.0492 (12)	0.0417 (12)	0.0397 (12)	−0.0049 (10)	−0.0033 (10)	0.0007 (9)
C7	0.0618 (15)	0.0530 (14)	0.0393 (14)	−0.0086 (12)	−0.0001 (11)	0.0052 (11)
C8	0.0773 (18)	0.0585 (17)	0.0583 (18)	0.0041 (14)	−0.0084 (15)	0.0211 (13)
C9	0.088 (2)	0.0675 (19)	0.0494 (17)	−0.0164 (17)	0.0147 (14)	−0.0199 (14)
C10	0.0536 (13)	0.0494 (14)	0.0446 (14)	−0.0061 (11)	−0.0038 (11)	−0.0004 (10)
C11	0.0491 (12)	0.0345 (11)	0.0377 (12)	−0.0008 (9)	0.0028 (9)	−0.0007 (9)
C12	0.0685 (18)	0.074 (2)	0.085 (2)	0.0149 (16)	−0.0254 (16)	−0.0040 (17)
C13	0.085 (2)	0.084 (2)	0.0569 (18)	−0.0011 (17)	0.0187 (15)	0.0051 (16)
C14	0.0793 (18)	0.0601 (17)	0.0496 (16)	−0.0130 (14)	−0.0044 (13)	−0.0115 (13)
N1	0.0541 (11)	0.0291 (9)	0.0376 (10)	0.0013 (8)	−0.0033 (8)	−0.0005 (7)
N2	0.0783 (15)	0.0663 (15)	0.0502 (14)	−0.0056 (13)	−0.0050 (12)	0.0214 (11)
N3	0.0822 (17)	0.0697 (16)	0.0449 (13)	−0.0143 (14)	−0.0069 (12)	−0.0080 (11)
O1	0.0847 (14)	0.0328 (9)	0.0784 (14)	−0.0010 (9)	−0.0094 (11)	−0.0062 (8)
S1	0.0656 (4)	0.0514 (4)	0.0651 (5)	0.0086 (3)	0.0065 (3)	−0.0160 (3)
S2	0.0670 (4)	0.0539 (4)	0.0538 (4)	0.0132 (3)	0.0032 (3)	0.0126 (3)

Geometric parameters (Å, º) top

C1—N1	1.448 (3)	C8—S2	1.706 (3)
C1—C11	1.491 (3)	C8—H8	0.9300
C1—C2	1.538 (3)	C9—N3	1.287 (4)
C1—H1	0.9800	C9—S1	1.713 (3)
C2—C3	1.497 (3)	C9—H9	0.9300
C2—H2A	0.9700	C10—C11	1.354 (3)
C2—H2B	0.9700	C10—N3	1.376 (3)
C3—O1	1.202 (3)	C10—C12	1.493 (4)
C3—C4	1.510 (3)	C11—S1	1.717 (2)
C4—C14	1.507 (3)	C12—H12A	0.9600
C4—C5	1.543 (3)	C12—H12B	0.9600
C4—H4	0.9800	C12—H12C	0.9600
C5—N1	1.458 (3)	C13—H13A	0.9600
C5—C6	1.496 (3)	C13—H13B	0.9600
C5—H5	0.9800	C13—H13C	0.9600
C6—C7	1.352 (3)	C14—H14A	0.9600
C6—S2	1.723 (3)	C14—H14B	0.9600
C7—N2	1.384 (3)	C14—H14C	0.9600
C7—C13	1.492 (4)	N1—H1A	0.8600
C8—N2	1.289 (4)

N1—C1—C11	110.04 (18)	S2—C8—H8	122.4
N1—C1—C2	108.27 (18)	N3—C9—S1	115.9 (2)
C11—C1—C2	112.34 (19)	N3—C9—H9	122.0
N1—C1—H1	108.7	S1—C9—H9	122.0
C11—C1—H1	108.7	C11—C10—N3	115.1 (2)
C2—C1—H1	108.7	C11—C10—C12	126.5 (2)
C3—C2—C1	110.46 (19)	N3—C10—C12	118.3 (2)
C3—C2—H2A	109.6	C10—C11—C1	129.5 (2)
C1—C2—H2A	109.6	C10—C11—S1	110.05 (18)
C3—C2—H2B	109.6	C1—C11—S1	120.38 (17)
C1—C2—H2B	109.6	C10—C12—H12A	109.5
H2A—C2—H2B	108.1	C10—C12—H12B	109.5
O1—C3—C2	122.3 (2)	H12A—C12—H12B	109.5
O1—C3—C4	122.1 (2)	C10—C12—H12C	109.5
C2—C3—C4	115.58 (19)	H12A—C12—H12C	109.5
C14—C4—C3	112.6 (2)	H12B—C12—H12C	109.5
C14—C4—C5	113.6 (2)	C7—C13—H13A	109.5
C3—C4—C5	109.01 (18)	C7—C13—H13B	109.5
C14—C4—H4	107.1	H13A—C13—H13B	109.5
C3—C4—H4	107.1	C7—C13—H13C	109.5
C5—C4—H4	107.1	H13A—C13—H13C	109.5
N1—C5—C6	108.96 (18)	H13B—C13—H13C	109.5
N1—C5—C4	109.88 (18)	C4—C14—H14A	109.5
C6—C5—C4	111.90 (18)	C4—C14—H14B	109.5
N1—C5—H5	108.7	H14A—C14—H14B	109.5
C6—C5—H5	108.7	C4—C14—H14C	109.5
C4—C5—H5	108.7	H14A—C14—H14C	109.5
C7—C6—C5	130.0 (2)	H14B—C14—H14C	109.5
C7—C6—S2	109.81 (19)	C1—N1—C5	113.88 (17)
C5—C6—S2	120.19 (17)	C1—N1—H1A	123.1
C6—C7—N2	114.6 (2)	C5—N1—H1A	123.1
C6—C7—C13	126.8 (3)	C8—N2—C7	111.0 (2)
N2—C7—C13	118.5 (2)	C9—N3—C10	110.3 (2)
N2—C8—S2	115.3 (2)	C9—S1—C11	88.64 (14)
N2—C8—H8	122.4	C8—S2—C6	89.28 (14)

N1—C1—C2—C3	54.1 (2)	N3—C10—C11—S1	−0.1 (3)
C11—C1—C2—C3	175.84 (19)	C12—C10—C11—S1	177.6 (2)
C1—C2—C3—O1	127.6 (3)	N1—C1—C11—C10	−147.0 (2)
C1—C2—C3—C4	−51.0 (3)	C2—C1—C11—C10	92.3 (3)
O1—C3—C4—C14	−2.3 (3)	N1—C1—C11—S1	34.6 (3)
C2—C3—C4—C14	176.4 (2)	C2—C1—C11—S1	−86.1 (2)
O1—C3—C4—C5	−129.2 (2)	C11—C1—N1—C5	174.46 (18)
C2—C3—C4—C5	49.5 (3)	C2—C1—N1—C5	−62.4 (2)
C14—C4—C5—N1	−178.6 (2)	C6—C5—N1—C1	−174.67 (18)
C3—C4—C5—N1	−52.2 (2)	C4—C5—N1—C1	62.4 (2)
C14—C4—C5—C6	60.2 (3)	S2—C8—N2—C7	0.0 (3)
C3—C4—C5—C6	−173.35 (19)	C6—C7—N2—C8	0.6 (3)
N1—C5—C6—C7	131.6 (3)	C13—C7—N2—C8	−178.5 (3)
C4—C5—C6—C7	−106.6 (3)	S1—C9—N3—C10	−0.7 (3)
N1—C5—C6—S2	−48.5 (2)	C11—C10—N3—C9	0.5 (3)
C4—C5—C6—S2	73.2 (2)	C12—C10—N3—C9	−177.4 (3)
C5—C6—C7—N2	178.9 (2)	N3—C9—S1—C11	0.6 (2)
S2—C6—C7—N2	−0.9 (3)	C10—C11—S1—C9	−0.28 (19)
C5—C6—C7—C13	−2.1 (4)	C1—C11—S1—C9	178.4 (2)
S2—C6—C7—C13	178.0 (2)	N2—C8—S2—C6	−0.5 (3)
N3—C10—C11—C1	−178.6 (2)	C7—C6—S2—C8	0.8 (2)
C12—C10—C11—C1	−0.9 (4)	C5—C6—S2—C8	−179.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2ⁱ	0.93	2.49	3.365 (4)	157

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2ⁱ	0.93	2.49	3.365 (4)	156.8

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

We are grateful to Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Chennai, India, for the data collection.

References

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Volume 70| Part 9| September 2014| Page o1055

doi:10.1107/S1600536814018856

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

Crystal structure of 3-methyl-2,6-bis­­(4-methyl-1,3-thia­zol-5-yl)piperidin-4-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-methyl-2,6-bis(4-methyl-1,3-thiazol-5-yl)piperidin-4-one