[(4E)-3-Ethyl-1-methyl-2,6-di­phenyl­piperidin-4-yl­idene]amino 3-methyl­benzoate

Vinuchakkaravarthy, T.; Sivakumar, R.; Srinivasan, T.; Thanikachalam, V.; Velmurugan, D.

doi:10.1107/S1600536813024276

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1545

doi:10.1107/S1600536813024276

Open

access

[(4E)-3-Ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene]amino 3-methylbenzoate

T. Vinuchakkaravarthy,^a R. Sivakumar,^b T. Srinivasan,^a V. Thanikachalam ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai Campus (Guindy Campus), Chennai 600 025, India, and ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram 608 002, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 26 May 2013; accepted 30 August 2013; online 18 September 2013)

In the title compound, C₂₈H₃₀N₂O₂, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl rings and methyl group substituted on the heterocycle. In the crystal, C—H⋯π interactions result in chains of molecules running parallel to the a-axis direction.

Related literature

For the synthesis and background to the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009 , 2011 ). For crystal structures of related compounds, see: Park et al. (2012a ,b ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₈H₃₀N₂O₂
M_r = 426.54
Triclinic, $[P \overline 1]$
a = 10.5220 (15) Å
b = 11.8295 (16) Å
c = 11.987 (3) Å
α = 112.871 (11)°
β = 97.939 (11)°
γ = 110.123 (8)°
V = 1225.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.986, T_max = 0.986
18615 measured reflections
5042 independent reflections
3610 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.139
S = 1.03
5042 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.93	2.93	3.761 (2)	149
C23—H23⋯Cg1ⁱⁱ	0.93	2.89	3.730 (3)	151
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+3, -y+1, -z+1.

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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813024276/pv2635sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024276/pv2635Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813024276/pv2635Isup3.cml

checkCIF report

Comment top

Piperdin-4-one nucleus is an important pharmacophore due to its broad spectrum of biological actions ranging from antibacterial to anticancer (Parthiban et al., 2009; 2011). Hence, the synthesis and steriochemical analysis of piperdin-4-one nucleus based pharmacophores has gained much interest in the field of medicinal chemistry.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Park et al., 2012a; 2012b). The piperidone ring (N1/C1—/C5) adopts a chair conformation with puckering parameters: Q =0.570 (2) Å, θ = 177.6 (2)° and ϕ = 3439 (4)° (Cremer & Pople, 1975).

In the crystal, the molecules are stabilized by intermolecular C11—H11···Cg1ⁱ and C23—H23···Cg1ⁱⁱ hydrogen bond interactions, where Cg1 is the center of gravity of ring atoms involving C15—C20 of the interacting molecules, respectively (Table 1). The packing of the molecules within the crystal is shown in Fig. 2.

Related literature top

For the synthesis and background to the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009, 2011). For crystal structures of related compounds, see: Park et al. (2012a,b). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

3-Ethyl-2,6-diphenylpiperidin-4-one was synthesized by Mannich condensation using benzaldehyde (2 mol), ammonium acetate (1 mol) and ethyl methyl ketone (1 mol) in absolute ethanol and warmed for 30 min and stirred overnight at room temperature. The product was treated with methyl iodide (1.5 mol) in the presence of potassium carbonate (2 mol) in acetone (10 ml) and refluxed to give 1-methyl-3-ethyl-2,6-diphenylpiperidin-4-one. The oximation was done by hydroxylamine hydrochloride (2 mol) in presence of sodium acetate (2 mol) in ethanol (10 ml) and refluxed. The resulting oxime (0.5 g, 1.55 mmol) was stirred with dry pyridine (5 ml), added 3-methylbenzoic acid (0.23 g, 1.7 mmol) followed by phosphorus oxychloride (0.21 ml, 2.3 mmol) in dropwise addition and stirred at ambient temperature for 15 min; the progress of the reaction was monitored by thin layer chromatography. Upon completion of the reaction, saturated sodium bicarbonate solution (8 ml) was added to the reaction mixture, solid was formed and it was filtered and dried to get a white solid (0.58 g, 87.8%) which was recrystallized from ethanol to yield crystals suitable for X-ray crystallographic studies.

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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. The crystal packing arrangement of the title compound viewed down the b axis showing intermolecular C—H···π hydrogen bond interactions (dashed lines). symmetry codes: (i) 2-X,1-Y,1-Z (ii) 3-X,1-Y,1-Z

[(4E)-3-Ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene]amino 3-methylbenzoate top

Crystal data top

C₂₈H₃₀N₂O₂	Z = 2
M_r = 426.54	F(000) = 456
Triclinic, P1	D_x = 1.156 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5220 (15) Å	Cell parameters from 5087 reflections
b = 11.8295 (16) Å	θ = 1.9–26.5°
c = 11.987 (3) Å	µ = 0.07 mm⁻¹
α = 112.871 (11)°	T = 293 K
β = 97.939 (11)°	Block, colorless
γ = 110.123 (8)°	0.20 × 0.20 × 0.20 mm
V = 1225.5 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	5042 independent reflections
Radiation source: fine-focus sealed tube	3610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 26.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.986, T_max = 0.986	k = −14→14
18615 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0639P)² + 0.1881P] where P = (F_o² + 2F_c²)/3
5042 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₈H₃₀N₂O₂	γ = 110.123 (8)°
M_r = 426.54	V = 1225.5 (4) Å³
Triclinic, P1	Z = 2
a = 10.5220 (15) Å	Mo Kα radiation
b = 11.8295 (16) Å	µ = 0.07 mm⁻¹
c = 11.987 (3) Å	T = 293 K
α = 112.871 (11)°	0.20 × 0.20 × 0.20 mm
β = 97.939 (11)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5042 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3610 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.986	R_int = 0.023
18615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
5042 reflections	Δρ_min = −0.17 e Å⁻³
292 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	0.89609 (15)	0.09484 (14)	0.34733 (14)	0.0517 (3)
H1	0.9758	0.0793	0.3798	0.062*
C2	0.88999 (15)	0.21364 (15)	0.45884 (13)	0.0532 (3)
H2	0.8121	0.2300	0.4241	0.064*
C3	1.02600 (15)	0.33834 (14)	0.49960 (14)	0.0535 (3)
C4	1.04934 (17)	0.37330 (15)	0.39518 (14)	0.0571 (4)
H4A	1.1390	0.4536	0.4267	0.069*
H4B	0.9733	0.3934	0.3654	0.069*
C5	1.05203 (15)	0.25298 (14)	0.28511 (13)	0.0517 (3)
H5	1.1339	0.2390	0.3154	0.062*
C6	0.76059 (16)	−0.03556 (14)	0.29564 (14)	0.0542 (4)
C7	0.7643 (2)	−0.15236 (18)	0.29179 (19)	0.0775 (5)
H7	0.8509	−0.1509	0.3238	0.093*
C8	0.6392 (3)	−0.27266 (19)	0.2404 (2)	0.0977 (7)
H8	0.6432	−0.3515	0.2361	0.117*
C9	0.5122 (3)	−0.2753 (2)	0.1966 (2)	0.0937 (6)
H9	0.4288	−0.3555	0.1635	0.112*
C10	0.5065 (2)	−0.1611 (2)	0.20100 (19)	0.0807 (5)
H10	0.4189	−0.1630	0.1713	0.097*
C11	0.62958 (17)	−0.04179 (16)	0.24912 (16)	0.0639 (4)
H11	0.6241	0.0354	0.2502	0.077*
C12	0.85682 (19)	0.18214 (18)	0.56631 (16)	0.0724 (5)
H12A	0.7807	0.0907	0.5294	0.087*
H12B	0.9405	0.1839	0.6139	0.087*
C13	0.8129 (2)	0.2812 (3)	0.6574 (2)	0.1013 (7)
H13A	0.8910	0.3707	0.7004	0.152*
H13B	0.7872	0.2525	0.7191	0.152*
H13C	0.7327	0.2832	0.6105	0.152*
C14	1.31474 (16)	0.59266 (16)	0.75477 (14)	0.0573 (4)
C15	1.43652 (16)	0.71158 (16)	0.76655 (15)	0.0590 (4)
C16	1.51466 (19)	0.81891 (18)	0.88722 (18)	0.0763 (5)
H16	1.4912	0.8145	0.9579	0.092*
C17	1.6272 (2)	0.9324 (2)	0.9027 (3)	0.0959 (7)
H17	1.6793	1.0050	0.9839	0.115*
C18	1.6625 (2)	0.9387 (2)	0.7998 (3)	0.0988 (8)
H18	1.7391	1.0160	0.8119	0.119*
C19	1.5872 (2)	0.8331 (2)	0.6777 (2)	0.0920 (7)
C20	1.47272 (18)	0.71950 (19)	0.66290 (18)	0.0723 (5)
H20	1.4196	0.6475	0.5815	0.087*
C21	1.6253 (3)	0.8389 (4)	0.5631 (3)	0.1622 (15)
H21A	1.5714	0.8753	0.5285	0.243*
H21B	1.6037	0.7487	0.4997	0.243*
H21C	1.7253	0.8963	0.5878	0.243*
C22	1.07151 (17)	0.28834 (14)	0.17812 (14)	0.0547 (4)
C23	1.19935 (19)	0.31668 (16)	0.15166 (16)	0.0679 (4)
H23	1.2729	0.3102	0.1977	0.081*
C24	1.2191 (3)	0.35446 (18)	0.0577 (2)	0.0875 (6)
H24	1.3055	0.3727	0.0408	0.105*
C25	1.1128 (3)	0.36531 (19)	−0.0108 (2)	0.0965 (7)
H25	1.1268	0.3912	−0.0738	0.116*
C26	0.9851 (3)	0.3376 (2)	0.01431 (18)	0.0893 (6)
H26	0.9123	0.3446	−0.0321	0.107*
C27	0.9640 (2)	0.29925 (17)	0.10809 (15)	0.0687 (4)
H27	0.8771	0.2807	0.1243	0.082*
C28	0.9312 (2)	0.01436 (16)	0.14152 (17)	0.0701 (5)
H28A	0.9489	0.0364	0.0744	0.105*
H28B	0.8433	−0.0664	0.1083	0.105*
H28C	1.0079	−0.0012	0.1756	0.105*
N1	0.92147 (12)	0.12787 (11)	0.24286 (11)	0.0493 (3)
N2	1.10892 (13)	0.39464 (13)	0.61306 (12)	0.0616 (3)
O1	1.23463 (11)	0.50961 (11)	0.63113 (10)	0.0681 (3)
O2	1.28828 (14)	0.57319 (14)	0.84073 (11)	0.0882 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0478 (8)	0.0499 (8)	0.0622 (8)	0.0209 (7)	0.0187 (7)	0.0307 (7)
C2	0.0504 (8)	0.0505 (8)	0.0542 (8)	0.0156 (7)	0.0179 (6)	0.0255 (7)
C3	0.0539 (8)	0.0482 (8)	0.0518 (8)	0.0164 (7)	0.0176 (7)	0.0222 (7)
C4	0.0621 (9)	0.0454 (8)	0.0526 (8)	0.0131 (7)	0.0163 (7)	0.0221 (7)
C5	0.0467 (8)	0.0494 (8)	0.0586 (8)	0.0176 (7)	0.0188 (6)	0.0270 (7)
C6	0.0576 (9)	0.0454 (8)	0.0618 (8)	0.0195 (7)	0.0245 (7)	0.0279 (7)
C7	0.0865 (13)	0.0599 (11)	0.1044 (14)	0.0362 (10)	0.0408 (11)	0.0483 (10)
C8	0.126 (2)	0.0494 (11)	0.1286 (18)	0.0337 (12)	0.0604 (16)	0.0492 (12)
C9	0.0915 (16)	0.0567 (12)	0.1021 (15)	0.0041 (11)	0.0354 (12)	0.0313 (11)
C10	0.0603 (11)	0.0702 (12)	0.0894 (13)	0.0080 (9)	0.0193 (9)	0.0360 (10)
C11	0.0579 (9)	0.0524 (9)	0.0750 (10)	0.0160 (8)	0.0192 (8)	0.0312 (8)
C12	0.0696 (11)	0.0687 (11)	0.0636 (10)	0.0087 (9)	0.0225 (8)	0.0348 (9)
C13	0.0995 (16)	0.1203 (18)	0.0744 (12)	0.0333 (14)	0.0482 (11)	0.0423 (12)
C14	0.0551 (9)	0.0585 (9)	0.0520 (8)	0.0213 (8)	0.0133 (7)	0.0241 (7)
C15	0.0485 (8)	0.0579 (9)	0.0647 (9)	0.0204 (7)	0.0097 (7)	0.0285 (8)
C16	0.0624 (11)	0.0660 (11)	0.0757 (11)	0.0228 (9)	0.0083 (9)	0.0190 (9)
C17	0.0648 (12)	0.0629 (12)	0.1178 (18)	0.0174 (10)	0.0008 (12)	0.0214 (12)
C18	0.0517 (11)	0.0727 (14)	0.159 (2)	0.0133 (10)	0.0089 (13)	0.0625 (16)
C19	0.0600 (11)	0.1018 (16)	0.1250 (18)	0.0199 (12)	0.0197 (12)	0.0798 (15)
C20	0.0551 (9)	0.0785 (12)	0.0759 (11)	0.0147 (9)	0.0111 (8)	0.0449 (10)
C21	0.1018 (19)	0.216 (4)	0.180 (3)	0.011 (2)	0.0387 (19)	0.156 (3)
C22	0.0625 (9)	0.0416 (7)	0.0548 (8)	0.0174 (7)	0.0242 (7)	0.0205 (6)
C23	0.0717 (11)	0.0522 (9)	0.0771 (11)	0.0199 (8)	0.0379 (9)	0.0292 (8)
C24	0.1104 (16)	0.0569 (11)	0.0910 (14)	0.0218 (11)	0.0622 (13)	0.0335 (10)
C25	0.157 (2)	0.0591 (11)	0.0719 (12)	0.0315 (13)	0.0545 (14)	0.0364 (10)
C26	0.1257 (18)	0.0718 (12)	0.0653 (11)	0.0371 (12)	0.0196 (11)	0.0359 (10)
C27	0.0769 (11)	0.0651 (10)	0.0615 (9)	0.0275 (9)	0.0206 (8)	0.0307 (8)
C28	0.0791 (11)	0.0522 (9)	0.0778 (11)	0.0282 (9)	0.0415 (9)	0.0241 (8)
N1	0.0489 (7)	0.0413 (6)	0.0549 (6)	0.0166 (5)	0.0219 (5)	0.0207 (5)
N2	0.0531 (7)	0.0586 (8)	0.0584 (8)	0.0078 (6)	0.0162 (6)	0.0285 (6)
O1	0.0575 (7)	0.0676 (7)	0.0544 (6)	0.0030 (6)	0.0117 (5)	0.0287 (5)
O2	0.0914 (9)	0.0885 (9)	0.0587 (7)	0.0120 (7)	0.0212 (6)	0.0347 (7)

Geometric parameters (Å, º) top

C1—N1	1.4809 (17)	C14—O1	1.3511 (18)
C1—C6	1.515 (2)	C14—C15	1.482 (2)
C1—C2	1.547 (2)	C15—C20	1.376 (2)
C1—H1	0.9800	C15—C16	1.381 (2)
C2—C3	1.502 (2)	C16—C17	1.375 (3)
C2—C12	1.526 (2)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.358 (3)
C3—N2	1.2740 (19)	C17—H17	0.9300
C3—C4	1.4884 (19)	C18—C19	1.381 (3)
C4—C5	1.532 (2)	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.390 (2)
C4—H4B	0.9700	C19—C21	1.503 (3)
C5—N1	1.4699 (17)	C20—H20	0.9300
C5—C22	1.5142 (19)	C21—H21A	0.9600
C5—H5	0.9800	C21—H21B	0.9600
C6—C11	1.379 (2)	C21—H21C	0.9600
C6—C7	1.379 (2)	C22—C23	1.383 (2)
C7—C8	1.394 (3)	C22—C27	1.387 (2)
C7—H7	0.9300	C23—C24	1.380 (3)
C8—C9	1.352 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.367 (3)
C9—C10	1.354 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.375 (3)
C10—C11	1.380 (2)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.384 (2)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.516 (3)	C27—H27	0.9300
C12—H12A	0.9700	C28—N1	1.4666 (19)
C12—H12B	0.9700	C28—H28A	0.9600
C13—H13A	0.9600	C28—H28B	0.9600
C13—H13B	0.9600	C28—H28C	0.9600
C13—H13C	0.9600	N2—O1	1.4492 (16)
C14—O2	1.1883 (18)

N1—C1—C6	109.65 (11)	O2—C14—O1	124.24 (15)
N1—C1—C2	111.57 (11)	O2—C14—C15	125.66 (14)
C6—C1—C2	111.31 (11)	O1—C14—C15	110.08 (13)
N1—C1—H1	108.1	C20—C15—C16	119.39 (16)
C6—C1—H1	108.1	C20—C15—C14	122.82 (15)
C2—C1—H1	108.1	C16—C15—C14	117.79 (16)
C3—C2—C12	114.71 (12)	C17—C16—C15	119.9 (2)
C3—C2—C1	107.06 (11)	C17—C16—H16	120.1
C12—C2—C1	113.67 (12)	C15—C16—H16	120.1
C3—C2—H2	107.0	C18—C17—C16	120.2 (2)
C12—C2—H2	107.0	C18—C17—H17	119.9
C1—C2—H2	107.0	C16—C17—H17	119.9
N2—C3—C4	128.60 (13)	C17—C18—C19	121.6 (2)
N2—C3—C2	117.74 (13)	C17—C18—H18	119.2
C4—C3—C2	113.50 (12)	C19—C18—H18	119.2
C3—C4—C5	109.35 (12)	C18—C19—C20	117.8 (2)
C3—C4—H4A	109.8	C18—C19—C21	122.1 (2)
C5—C4—H4A	109.8	C20—C19—C21	120.2 (2)
C3—C4—H4B	109.8	C15—C20—C19	121.16 (18)
C5—C4—H4B	109.8	C15—C20—H20	119.4
H4A—C4—H4B	108.3	C19—C20—H20	119.4
N1—C5—C22	111.99 (11)	C19—C21—H21A	109.5
N1—C5—C4	110.54 (11)	C19—C21—H21B	109.5
C22—C5—C4	108.78 (11)	H21A—C21—H21B	109.5
N1—C5—H5	108.5	C19—C21—H21C	109.5
C22—C5—H5	108.5	H21A—C21—H21C	109.5
C4—C5—H5	108.5	H21B—C21—H21C	109.5
C11—C6—C7	117.80 (15)	C23—C22—C27	118.32 (15)
C11—C6—C1	121.02 (12)	C23—C22—C5	120.77 (15)
C7—C6—C1	121.17 (14)	C27—C22—C5	120.84 (14)
C6—C7—C8	120.51 (19)	C24—C23—C22	120.75 (19)
C6—C7—H7	119.7	C24—C23—H23	119.6
C8—C7—H7	119.7	C22—C23—H23	119.6
C9—C8—C7	120.33 (18)	C25—C24—C23	120.65 (19)
C9—C8—H8	119.8	C25—C24—H24	119.7
C7—C8—H8	119.8	C23—C24—H24	119.7
C8—C9—C10	119.89 (19)	C24—C25—C26	119.32 (18)
C8—C9—H9	120.1	C24—C25—H25	120.3
C10—C9—H9	120.1	C26—C25—H25	120.3
C9—C10—C11	120.6 (2)	C25—C26—C27	120.5 (2)
C9—C10—H10	119.7	C25—C26—H26	119.7
C11—C10—H10	119.7	C27—C26—H26	119.7
C6—C11—C10	120.88 (16)	C26—C27—C22	120.43 (18)
C6—C11—H11	119.6	C26—C27—H27	119.8
C10—C11—H11	119.6	C22—C27—H27	119.8
C13—C12—C2	113.43 (16)	N1—C28—H28A	109.5
C13—C12—H12A	108.9	N1—C28—H28B	109.5
C2—C12—H12A	108.9	H28A—C28—H28B	109.5
C13—C12—H12B	108.9	N1—C28—H28C	109.5
C2—C12—H12B	108.9	H28A—C28—H28C	109.5
H12A—C12—H12B	107.7	H28B—C28—H28C	109.5
C12—C13—H13A	109.5	C28—N1—C5	108.74 (11)
C12—C13—H13B	109.5	C28—N1—C1	109.56 (11)
H13A—C13—H13B	109.5	C5—N1—C1	113.06 (11)
C12—C13—H13C	109.5	C3—N2—O1	108.75 (11)
H13A—C13—H13C	109.5	C14—O1—N2	113.11 (11)
H13B—C13—H13C	109.5

N1—C1—C2—C3	−55.08 (15)	C16—C17—C18—C19	0.3 (3)
C6—C1—C2—C3	−177.93 (11)	C17—C18—C19—C20	0.4 (3)
N1—C1—C2—C12	177.19 (12)	C17—C18—C19—C21	−179.9 (2)
C6—C1—C2—C12	54.34 (16)	C16—C15—C20—C19	0.5 (3)
C12—C2—C3—N2	9.1 (2)	C14—C15—C20—C19	179.61 (16)
C1—C2—C3—N2	−118.05 (15)	C18—C19—C20—C15	−0.8 (3)
C12—C2—C3—C4	−175.05 (13)	C21—C19—C20—C15	179.5 (2)
C1—C2—C3—C4	57.83 (16)	N1—C5—C22—C23	−129.64 (14)
N2—C3—C4—C5	116.68 (18)	C4—C5—C22—C23	107.88 (16)
C2—C3—C4—C5	−58.66 (17)	N1—C5—C22—C27	53.35 (18)
C3—C4—C5—N1	55.01 (16)	C4—C5—C22—C27	−69.13 (17)
C3—C4—C5—C22	178.37 (12)	C27—C22—C23—C24	−0.2 (2)
N1—C1—C6—C11	−65.70 (17)	C5—C22—C23—C24	−177.26 (14)
C2—C1—C6—C11	58.24 (18)	C22—C23—C24—C25	0.3 (3)
N1—C1—C6—C7	113.34 (16)	C23—C24—C25—C26	−0.3 (3)
C2—C1—C6—C7	−122.72 (16)	C24—C25—C26—C27	0.1 (3)
C11—C6—C7—C8	1.1 (3)	C25—C26—C27—C22	0.0 (3)
C1—C6—C7—C8	−178.01 (16)	C23—C22—C27—C26	0.0 (2)
C6—C7—C8—C9	−1.7 (3)	C5—C22—C27—C26	177.10 (15)
C7—C8—C9—C10	0.9 (3)	C22—C5—N1—C28	61.00 (15)
C8—C9—C10—C11	0.4 (3)	C4—C5—N1—C28	−177.53 (12)
C7—C6—C11—C10	0.3 (2)	C22—C5—N1—C1	−177.08 (11)
C1—C6—C11—C10	179.37 (15)	C4—C5—N1—C1	−55.61 (14)
C9—C10—C11—C6	−1.1 (3)	C6—C1—N1—C28	−58.12 (15)
C3—C2—C12—C13	71.5 (2)	C2—C1—N1—C28	178.09 (12)
C1—C2—C12—C13	−164.88 (15)	C6—C1—N1—C5	−179.58 (11)
O2—C14—C15—C20	170.94 (17)	C2—C1—N1—C5	56.63 (15)
O1—C14—C15—C20	−10.5 (2)	C4—C3—N2—O1	3.1 (2)
O2—C14—C15—C16	−10.0 (2)	C2—C3—N2—O1	178.31 (12)
O1—C14—C15—C16	168.57 (14)	O2—C14—O1—N2	1.7 (2)
C20—C15—C16—C17	0.2 (3)	C15—C14—O1—N2	−176.83 (11)
C14—C15—C16—C17	−178.97 (16)	C3—N2—O1—C14	166.95 (14)
C15—C16—C17—C18	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	2.93	3.761 (2)	149
C23—H23···Cg1ⁱⁱ	0.93	2.89	3.730 (3)	151

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	2.93	3.761 (2)	149
C23—H23···Cg1ⁱⁱ	0.93	2.89	3.730 (3)	151

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

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection·TV, TS and DV thank the UGC (SAP–CAS) for providing facilities to the department.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012a). Acta Cryst. E68, o524. Web of Science CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o525. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Balasubramanian, S., Aridoss, G. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 2981–2985. Web of Science CSD CrossRef PubMed CAS Google Scholar
Parthiban, P., Pallela, R., Kim, S. K., Park, D. H. & Jeong, Y. T. (2011). Bioorg. Med. Chem. Lett. 21, 6678–6686. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1545

doi:10.1107/S1600536813024276

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

[(4E)-3-Ethyl-1-methyl-2,6-di­phenyl­piperidin-4-yl­­idene]amino 3-methyl­benzoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[(4E)-3-Ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene]amino 3-methylbenzoate