(4E)-1-Phenyl-4-[(piperidin-1-yl)methyl­idene]pyrazolidine-3,5-dione

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Ahmed, E.A.; Mohamed, A.F.; Albayati, M.R.

doi:10.1107/S2414314616010282

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x161028

doi:10.1107/S2414314616010282

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(4E)-1-Phenyl-4-[(piperidin-1-yl)methylidene]pyrazolidine-3,5-dione

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Eman A. Ahmed,^e Alaa F. Mohamed ^f and Mustafa R. Albayati ^g ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, ^fNational Organization for Drug Control and Research (NODCAR), Giza, Egypt, and ^gKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 June 2016; accepted 24 June 2016; online 30 June 2016)

In the title compound, C₁₅H₁₇N₃O₂, the dihedral angle between the planes of the pyrazolidine and phenyl rings is 29.91 (6)°. The piperidine ring adopts a chair conformation. In the crystal, molecules are linked into chains running parallel to the a-axis direction by a combination of N—H⋯O and C—H⋯O hydrogen bonds. Furthermore, there exist C—H⋯π interactions and π–π stacking interactions [centroid-to-centroid distance = 3.5274 (10) Å] between the pyrazolidine rings of adjacent molecules.

Keywords: crystal structure; pyrazolidindiones; β-unsaturated carbonyl compounds.

CCDC reference: 1487642

Structure description

Pyrazolone derivatives have diverse pharmacological properties, such as cytotoxic, anti-inflammatory, antimicrobial, antioxidant, antifungal, antiviral and oral hypoglycaemic activity (Kumar et al., 2012 ). As part of our studies in this area, the synthesis and structure of the title compound are reported.

In the title compound, the piperidine ring (atoms N3/C5–C9) adopts a chair conformation, with the puckering parameters Q_T = 0.547 (2) Å, θ = 176.2 (2)° and φ = 344 (3)°. The dihedral angle between the planes of the phenyl and pyrazolidine rings is 29.91 (6)°. The molecular conformation is partially determined by an intramolecular C5—H5B⋯O1 hydrogen bond (Table 1 and Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.94 (2)	1.86 (2)	2.8008 (18)	171 (2)
C5—H5B⋯O1	0.99	2.24	2.979 (2)	131
C9—H9A⋯O1ⁱⁱ	0.99	2.51	3.421 (2)	152
C11—H11⋯O2ⁱⁱⁱ	0.95	2.52	3.471 (2)	178
C9—H9B⋯Cg3^iv	0.99	2.91	3.741 (2)	143
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

Figure 1
The title molecule, shown with 50% probability displacement ellipsoids. The intramolecular C—H⋯O hydrogen bond is shown by a dotted line.

In the crystal, molecules pack in columns running parallel to the a axis which are assembled by N2—H2⋯O1ⁱ and a combination of C9—H9A⋯O1ⁱⁱ and C11—H11⋯O2ⁱⁱⁱ hydrogen bonds [symmetry codes: (i) −x + 2, −y + 1, −z + 1; (ii) x − 1, y, z; (iii) x + 1, y, z] (Table 1 and Figs. 2 and 3). In addition, C—H⋯π interactions (Table 1) and π–π stacking interactions [Cg1⋯Cg1(−x + 1, −y + 1, −z + 1) = 3.5274 (10) Å; where Cg1 is the centroid of the pyrazolidine ring (N1/N2/C1–C3)] are observed in the crystal structure.

Figure 2
The packing, viewed along the a axis, with intermolecular N—H⋯O and C—H⋯O hydrogen bonds shown, respectively, as blue and black dotted lines.

Figure 3
Side view of a portion of the central chain shown in Fig. 2

, with intermolecular N—H⋯O and C—H⋯O hydrogen bonds shown, respectively, as blue and black dotted lines.

Synthesis and crystallization

A mixture of 1 mmol (231.3 mg) of 4-[(dimethylamino)methylidene]-1-phenylpyrazolidine-3,5-dione and 1 mmol (85 mg) of piperidine was refluxed in 30 ml dioxane for 2 h. The obtained solid product was collected under vacuum and recrystallized from ethanol to yield colourless rods of the title compound (yield 95%; m.p. 518–520 K).

Refinement

Trial refinements with both the single-component reflection file extracted from the full data set with TWINABS (Sheldrick, 2009 ) and with the complete two-component reflection file indicated the former to provide superior results. Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₃O₂
M_r	271.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	6.3184 (2), 15.4673 (6), 13.2528 (5)
β (°)	98.762 (2)
V (Å³)	1280.06 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.78
Crystal size (mm)	0.12 × 0.07 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009)
T_min, T_max	0.81, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	16143, 2493, 1946
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.109, 1.03
No. of reflections	2493
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Bruker, 2016).

Structural data

CCDC reference: 1487642

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616010282/hb4060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616010282/hb4060Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616010282/hb4060Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2016).

(4E)-1-Phenyl-4-[(piperidin-1-yl)methylidene]pyrazolidine-3,5-dione top

Crystal data top

C₁₅H₁₇N₃O₂	F(000) = 576
M_r = 271.32	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 6.3184 (2) Å	Cell parameters from 6240 reflections
b = 15.4673 (6) Å	θ = 4.4–72.2°
c = 13.2528 (5) Å	µ = 0.78 mm⁻¹
β = 98.762 (2)°	T = 150 K
V = 1280.06 (8) Å³	Rod, colourless
Z = 4	0.12 × 0.07 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2493 independent reflections
Radiation source: INCOATEC IµS micro–focus source	1946 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.053
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.5°, θ_min = 4.4°
ω scans	h = −7→7
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −18→18
T_min = 0.81, T_max = 0.97	l = −16→16
16143 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.055P)² + 0.3794P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2493 reflections	Δρ_max = 0.21 e Å⁻³
186 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (6)

Special details top

Experimental. Analysis of 961 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the a axis. The raw data were processed using the multi-component version ofSAINT under control of the two-component orientation file generated by CELL_NOW.

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. 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.84360 (19)	0.52001 (8)	0.37140 (9)	0.0280 (3)
O2	0.31975 (19)	0.66186 (8)	0.53428 (9)	0.0305 (3)
N1	0.6720 (2)	0.61623 (9)	0.57952 (10)	0.0246 (3)
N2	0.8306 (2)	0.58417 (9)	0.52548 (10)	0.0239 (3)
H2	0.943 (4)	0.5538 (15)	0.5650 (16)	0.041 (6)*
N3	0.3412 (2)	0.56277 (10)	0.24051 (10)	0.0273 (3)
C1	0.7405 (3)	0.56111 (10)	0.42895 (12)	0.0230 (4)
C2	0.5203 (3)	0.59034 (11)	0.41576 (12)	0.0225 (4)
C3	0.4811 (3)	0.62622 (11)	0.51260 (12)	0.0231 (4)
C4	0.3478 (3)	0.58062 (11)	0.33819 (12)	0.0245 (4)
H4	0.2116	0.5881	0.3590	0.029*
C5	0.5288 (3)	0.56342 (15)	0.18738 (13)	0.0355 (5)
H5A	0.5579	0.5040	0.1653	0.043*
H5B	0.6558	0.5836	0.2346	0.043*
C6	0.4900 (3)	0.62225 (14)	0.09547 (14)	0.0346 (4)
H6A	0.6133	0.6186	0.0577	0.042*
H6B	0.4789	0.6827	0.1185	0.042*
C7	0.2870 (3)	0.59810 (14)	0.02483 (14)	0.0362 (5)
H7A	0.3024	0.5396	−0.0036	0.043*
H7B	0.2619	0.6395	−0.0327	0.043*
C8	0.0982 (3)	0.59946 (14)	0.08315 (14)	0.0354 (5)
H8A	0.0734	0.6594	0.1047	0.042*
H8B	−0.0320	0.5799	0.0378	0.042*
C9	0.1371 (3)	0.54169 (13)	0.17623 (13)	0.0314 (4)
H9A	0.0185	0.5488	0.2165	0.038*
H9B	0.1392	0.4806	0.1543	0.038*
C10	0.7371 (3)	0.65691 (11)	0.67417 (12)	0.0239 (4)
C11	0.9487 (3)	0.68439 (11)	0.70058 (13)	0.0280 (4)
H11	1.0486	0.6769	0.6545	0.034*
C12	1.0114 (3)	0.72278 (12)	0.79519 (14)	0.0336 (4)
H12	1.1551	0.7417	0.8136	0.040*
C13	0.8670 (3)	0.73380 (12)	0.86315 (14)	0.0357 (5)
H13	0.9109	0.7605	0.9275	0.043*
C14	0.6583 (3)	0.70556 (12)	0.83624 (14)	0.0332 (4)
H14	0.5591	0.7131	0.8827	0.040*
C15	0.5910 (3)	0.66642 (11)	0.74251 (13)	0.0277 (4)
H15	0.4479	0.6465	0.7252	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0264 (6)	0.0348 (7)	0.0231 (6)	0.0078 (5)	0.0045 (5)	−0.0008 (5)
O2	0.0232 (6)	0.0392 (7)	0.0293 (7)	0.0055 (5)	0.0044 (5)	−0.0031 (5)
N1	0.0206 (7)	0.0311 (8)	0.0220 (7)	0.0034 (6)	0.0028 (6)	−0.0030 (6)
N2	0.0189 (7)	0.0306 (8)	0.0216 (7)	0.0049 (6)	0.0014 (6)	−0.0017 (6)
N3	0.0210 (7)	0.0391 (9)	0.0215 (7)	0.0018 (6)	0.0025 (6)	0.0006 (6)
C1	0.0229 (8)	0.0239 (8)	0.0222 (8)	0.0005 (6)	0.0029 (7)	0.0017 (6)
C2	0.0218 (8)	0.0246 (8)	0.0209 (8)	0.0010 (6)	0.0028 (6)	0.0011 (6)
C3	0.0204 (8)	0.0252 (8)	0.0234 (8)	−0.0002 (6)	0.0027 (6)	0.0011 (6)
C4	0.0225 (8)	0.0272 (8)	0.0241 (8)	0.0011 (6)	0.0042 (7)	0.0021 (6)
C5	0.0226 (9)	0.0612 (13)	0.0233 (9)	0.0078 (8)	0.0054 (7)	0.0039 (8)
C6	0.0312 (10)	0.0435 (11)	0.0297 (10)	−0.0031 (8)	0.0063 (8)	0.0024 (8)
C7	0.0343 (10)	0.0466 (12)	0.0270 (10)	0.0050 (8)	0.0028 (8)	0.0054 (8)
C8	0.0276 (10)	0.0491 (12)	0.0277 (10)	0.0065 (8)	−0.0012 (8)	−0.0009 (8)
C9	0.0230 (9)	0.0449 (11)	0.0255 (9)	−0.0037 (7)	0.0012 (7)	−0.0037 (7)
C10	0.0279 (9)	0.0216 (8)	0.0210 (8)	0.0028 (6)	0.0003 (7)	0.0001 (6)
C11	0.0272 (9)	0.0283 (9)	0.0280 (9)	0.0002 (7)	0.0027 (7)	−0.0010 (7)
C12	0.0332 (10)	0.0303 (10)	0.0344 (10)	0.0000 (7)	−0.0043 (8)	−0.0048 (7)
C13	0.0457 (11)	0.0328 (10)	0.0260 (9)	0.0082 (8)	−0.0032 (8)	−0.0065 (7)
C14	0.0401 (11)	0.0340 (10)	0.0257 (9)	0.0105 (8)	0.0056 (8)	−0.0016 (7)
C15	0.0285 (9)	0.0292 (9)	0.0252 (9)	0.0038 (7)	0.0037 (7)	0.0009 (7)

Geometric parameters (Å, º) top

O1—C1	1.250 (2)	C7—C8	1.517 (3)
O2—C3	1.231 (2)	C7—H7A	0.9900
N1—C3	1.393 (2)	C7—H7B	0.9900
N1—C10	1.408 (2)	C8—C9	1.513 (3)
N1—N2	1.4078 (19)	C8—H8A	0.9900
N2—C1	1.366 (2)	C8—H8B	0.9900
N2—H2	0.94 (2)	C9—H9A	0.9900
N3—C4	1.318 (2)	C9—H9B	0.9900
N3—C5	1.468 (2)	C10—C15	1.396 (2)
N3—C9	1.470 (2)	C10—C11	1.396 (2)
C1—C2	1.448 (2)	C11—C12	1.389 (2)
C2—C4	1.388 (2)	C11—H11	0.9500
C2—C3	1.454 (2)	C12—C13	1.387 (3)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.510 (3)	C13—C14	1.383 (3)
C5—H5A	0.9900	C13—H13	0.9500
C5—H5B	0.9900	C14—C15	1.389 (2)
C6—C7	1.515 (3)	C14—H14	0.9500
C6—H6A	0.9900	C15—H15	0.9500
C6—H6B	0.9900

C3—N1—C10	128.69 (14)	C8—C7—H7A	109.7
C3—N1—N2	109.25 (13)	C6—C7—H7B	109.7
C10—N1—N2	118.48 (13)	C8—C7—H7B	109.7
C1—N2—N1	109.92 (13)	H7A—C7—H7B	108.2
C1—N2—H2	124.2 (13)	C9—C8—C7	111.39 (16)
N1—N2—H2	115.4 (13)	C9—C8—H8A	109.4
C4—N3—C5	124.23 (15)	C7—C8—H8A	109.4
C4—N3—C9	120.63 (15)	C9—C8—H8B	109.4
C5—N3—C9	115.13 (14)	C7—C8—H8B	109.4
O1—C1—N2	121.49 (15)	H8A—C8—H8B	108.0
O1—C1—C2	131.76 (15)	N3—C9—C8	111.15 (16)
N2—C1—C2	106.70 (14)	N3—C9—H9A	109.4
C4—C2—C1	133.42 (16)	C8—C9—H9A	109.4
C4—C2—C3	118.37 (15)	N3—C9—H9B	109.4
C1—C2—C3	107.60 (14)	C8—C9—H9B	109.4
O2—C3—N1	124.67 (15)	H9A—C9—H9B	108.0
O2—C3—C2	129.46 (15)	C15—C10—C11	120.53 (16)
N1—C3—C2	105.81 (14)	C15—C10—N1	119.54 (15)
N3—C4—C2	130.85 (16)	C11—C10—N1	119.88 (15)
N3—C4—H4	114.6	C12—C11—C10	119.13 (17)
C2—C4—H4	114.6	C12—C11—H11	120.4
N3—C5—C6	110.34 (15)	C10—C11—H11	120.4
N3—C5—H5A	109.6	C13—C12—C11	120.89 (18)
C6—C5—H5A	109.6	C13—C12—H12	119.6
N3—C5—H5B	109.6	C11—C12—H12	119.6
C6—C5—H5B	109.6	C14—C13—C12	119.30 (17)
H5A—C5—H5B	108.1	C14—C13—H13	120.3
C5—C6—C7	111.58 (17)	C12—C13—H13	120.3
C5—C6—H6A	109.3	C13—C14—C15	121.20 (18)
C7—C6—H6A	109.3	C13—C14—H14	119.4
C5—C6—H6B	109.3	C15—C14—H14	119.4
C7—C6—H6B	109.3	C14—C15—C10	118.93 (17)
H6A—C6—H6B	108.0	C14—C15—H15	120.5
C6—C7—C8	109.83 (16)	C10—C15—H15	120.5
C6—C7—H7A	109.7

C3—N1—N2—C1	−8.90 (19)	C4—N3—C5—C6	−125.26 (19)
C10—N1—N2—C1	−169.40 (14)	C9—N3—C5—C6	53.8 (2)
N1—N2—C1—O1	−169.98 (15)	N3—C5—C6—C7	−54.8 (2)
N1—N2—C1—C2	7.91 (18)	C5—C6—C7—C8	56.4 (2)
O1—C1—C2—C4	2.8 (3)	C6—C7—C8—C9	−55.3 (2)
N2—C1—C2—C4	−174.77 (18)	C4—N3—C9—C8	125.88 (18)
O1—C1—C2—C3	173.40 (17)	C5—N3—C9—C8	−53.2 (2)
N2—C1—C2—C3	−4.19 (18)	C7—C8—C9—N3	53.1 (2)
C10—N1—C3—O2	−13.6 (3)	C3—N1—C10—C15	42.5 (2)
N2—N1—C3—O2	−171.57 (16)	N2—N1—C10—C15	−161.32 (15)
C10—N1—C3—C2	163.79 (16)	C3—N1—C10—C11	−139.96 (18)
N2—N1—C3—C2	5.86 (18)	N2—N1—C10—C11	16.2 (2)
C4—C2—C3—O2	−11.6 (3)	C15—C10—C11—C12	−1.1 (3)
C1—C2—C3—O2	176.20 (18)	N1—C10—C11—C12	−178.65 (16)
C4—C2—C3—N1	171.17 (15)	C10—C11—C12—C13	0.1 (3)
C1—C2—C3—N1	−1.07 (18)	C11—C12—C13—C14	0.4 (3)
C5—N3—C4—C2	−11.1 (3)	C12—C13—C14—C15	0.0 (3)
C9—N3—C4—C2	169.92 (18)	C13—C14—C15—C10	−1.0 (3)
C1—C2—C4—N3	−21.8 (3)	C11—C10—C15—C14	1.5 (3)
C3—C2—C4—N3	168.43 (17)	N1—C10—C15—C14	179.07 (16)

Hydrogen-bond geometry (Å, º) top

Cg3 is a centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.94 (2)	1.86 (2)	2.8008 (18)	171 (2)
C5—H5B···O1	0.99	2.24	2.979 (2)	131
C9—H9A···O1ⁱⁱ	0.99	2.51	3.421 (2)	152
C11—H11···O2ⁱⁱⁱ	0.95	2.52	3.471 (2)	178
C9—H9B···Cg3^iv	0.99	2.91	3.741 (2)	143

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

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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