Methyl ({[(4E)-1,3-dimethyl-2,6-di­phenyl­piperidin-4-yl­idene]amino}­oxy)acetate

Mohandas, T.; Pillai, M.V.; Vidhyasagar, T.; Pasupathy, A.; Sakthivel, P.

doi:10.1107/S1600536814006667

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o513

doi:10.1107/S1600536814006667

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Methyl ({[(4E)-1,3-dimethyl-2,6-diphenylpiperidin-4-ylidene]amino}oxy)acetate

T. Mohandas,^a M. Velayutham Pillai,^b T. Vidhyasagar,^b A. Pasupathy ^c and P. Sakthivel ^d ^*

^aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 23 January 2014; accepted 26 March 2014; online 2 April 2014)

In the title compound, C₂₂H₂₆N₂O₃, the piperidine ring exhibits a chair conformation. The phenyl rings attached to the piperidine at the 2- and 6-positions have axial orientations. These rings make a dihedral angle of 49.75 (11)°. The aminooxy acetate group attached at the 4-position has an equatorial orientation. In the crystal, inversion dimers linked by pairs of C—H⋯π interactions occur.

CCDC reference: 993682

Related literature

For background and the importance of oxime ethers, see: Crichlow et al. (2007 ). For a study of the in vitro antiproliferative activity of oxyme ether derivatives, see: Parthiban et al. (2011 ). For their effects on the senescence of cut carnation flowers, see: Zeng et al. (2012 ). For ring conformations, see: Cremer & Pople (1975 ). For related structures, see: Park et al. (2012a ,b ).

Experimental

Crystal data

C₂₂H₂₆N₂O₃
M_r = 366.45
Monoclinic, P 2₁ /c
a = 8.1662 (9) Å
b = 15.0229 (16) Å
c = 16.2889 (19) Å
β = 93.903 (6)°
V = 1993.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.972, T_max = 0.976
17582 measured reflections
17582 independent reflections
12046 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.214
S = 1.06
17582 reflections
249 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯Cg2ⁱ	0.96	2.76	3.525 (3)	138.00
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and 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: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 993682

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814006667/rk2422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006667/rk2422Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006667/rk2422Isup3.cml

checkCIF report

Comment top

Oxime ethers are serving as important synthetic intermediate and have been employed as starting materials for both synthetic and medicinal chemistry (Crichlow et al., 2007).

Oxime ether derivatives of 2,6-diphenyl-piperidine–4-one with N-methyl substituent enhanced the efficacy of the in vitro antiproliferative activity against human cervical carcinoma cell lines (Parthiban et al., 2011). Recently oxime ether derivatives of aminooxy acetic acid were synthesized and studied for their effects on the senescence of cut carnation flowers (Zeng et al., 2012). Due to the above importance, the crystal data for the title compound was carried out by X–ray diffraction.

Piperidine ring (C7–C11/N1) exists in a chair conformation with the puckering parameter Q = 0.5566Å, θ = 1.70 (19)°, ϕ= 23 (7)° (syn periplanar).

The bond distances and bond angles in the title compound agree very well with the corresponding values reported in closely related compound (Park et al., 2012a; 2012b).

The main plane of piperidine ring makes the dihedral angle of 81.82° and 86.73° with the phenyl rings at the 2 and 6 positions respectively. The dihedral angle between the two phenyl rings is 49.75°. The crystal is stabilized by C—H···O interactions. The packing is further stabilized by C—H···π and C22—H22B···Cg2ⁱ interactions, where Cg2 is the centroid of (C1–C6) ring. Symmetry code: (i) 1-x, 1-y, 1-z.

Related literature top

For background and the imoprtance of oxime ethers, see: Crichlow et al. (2007). For a study of the in vitro antiproliferative activity of oxyme ether derivatives, see: Parthiban et al. (2011). For their effects on the senescence of cut carnation flowers, see: Zeng et al. (2012). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Park et al. (2012a,b).

Experimental top

To a stirred mixture of 1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime (0.88 g, 3 mmol) and K₂CO₃ (0.42 g, 1 eq.) in acetonitrile (15 ml) at 353 K, methyl chloroacetate (0.25 ml, 1 eq) was added dropwise over a period of 5 min and stirring continued for 7.5 hrs at the same condition. The progress of the reaction was monitored by TLC. After completion of the reaction K₂CO₃ was removed by filtration and the solvent was evaporated to getcrude product. Pure product was obtained by coloumn chromotography using petroleum ether/ethyl acetate (9.5/0.5) mixture as the eluent. Yield: 0.77 g (70%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and labelling scheme for title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A packing diagram for title compound.

Methyl ({[(4E)-1,3-dimethyl-2,6-diphenylpiperidin-4-ylidene]amino}oxy)acetate top

Crystal data top

C₂₂H₂₆N₂O₃	F(000) = 784
M_r = 366.45	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17582 reflections
a = 8.1662 (9) Å	θ = 1.9–25.7°
b = 15.0229 (16) Å	µ = 0.08 mm⁻¹
c = 16.2889 (19) Å	T = 295 K
β = 93.903 (6)°	Block, colourless
V = 1993.7 (4) Å³	0.35 × 0.35 × 0.30 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	17582 independent reflections
Radiation source: fine–focus sealed tube	12046 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 18.4 pixels mm^-1	θ_max = 25.7°, θ_min = 1.9°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→18
T_min = 0.972, T_max = 0.976	l = −19→16
17582 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.214	w = 1/[σ²(F_o²) + (0.0418P)² + 3.4429P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
17582 reflections	Δρ_max = 0.31 e Å⁻³
249 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (7)

Crystal data top

C₂₂H₂₆N₂O₃	V = 1993.7 (4) Å³
M_r = 366.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1662 (9) Å	µ = 0.08 mm⁻¹
b = 15.0229 (16) Å	T = 295 K
c = 16.2889 (19) Å	0.35 × 0.35 × 0.30 mm
β = 93.903 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	17582 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	12046 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.976	R_int = 0.000
17582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
17582 reflections	Δρ_min = −0.29 e Å⁻³
249 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance–covariance matrix. The cell s.u.'s are taken into account in the estimation of distances, angles and torsion angles.

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
O1	0.68977 (19)	0.49995 (10)	0.43999 (8)	0.0606 (6)
O2	0.7546 (2)	0.43922 (10)	0.65189 (9)	0.0649 (6)
O3	0.6248 (2)	0.36381 (11)	0.54968 (10)	0.0771 (7)
N1	0.83698 (18)	0.48449 (10)	0.16289 (9)	0.0383 (5)
N2	0.7999 (2)	0.43901 (11)	0.40538 (10)	0.0467 (6)
C1	0.5090 (3)	0.55836 (14)	0.10496 (12)	0.0499 (7)
C2	0.3910 (3)	0.60714 (17)	0.06143 (13)	0.0619 (9)
C3	0.3809 (3)	0.69704 (19)	0.07252 (15)	0.0684 (10)
C4	0.4887 (3)	0.73784 (16)	0.12720 (17)	0.0680 (10)
C5	0.6074 (3)	0.68953 (14)	0.17255 (14)	0.0529 (8)
C6	0.6190 (2)	0.59865 (12)	0.16163 (11)	0.0381 (7)
C7	0.7430 (2)	0.54460 (12)	0.21323 (11)	0.0394 (7)
C8	0.6541 (2)	0.49215 (14)	0.27705 (11)	0.0459 (7)
C9	0.7736 (2)	0.43693 (13)	0.32754 (11)	0.0390 (7)
C10	0.8732 (2)	0.37623 (12)	0.27849 (11)	0.0401 (7)
C11	0.9567 (2)	0.43131 (12)	0.21322 (11)	0.0387 (6)
C12	1.0538 (3)	0.37151 (13)	0.15962 (12)	0.0427 (7)
C13	1.2220 (3)	0.37356 (15)	0.16396 (14)	0.0583 (9)
C14	1.3111 (3)	0.31608 (18)	0.11732 (17)	0.0757 (11)
C15	1.2312 (4)	0.25588 (19)	0.06656 (17)	0.0820 (11)
C16	1.0624 (4)	0.25213 (18)	0.06119 (15)	0.0792 (11)
C17	0.9742 (3)	0.30997 (15)	0.10737 (13)	0.0575 (8)
C18	0.9212 (3)	0.53774 (15)	0.10310 (13)	0.0606 (9)
C19	0.9942 (3)	0.31926 (14)	0.32933 (13)	0.0579 (8)
C20	0.7357 (3)	0.50883 (14)	0.52479 (11)	0.0542 (8)
C21	0.6970 (3)	0.42816 (15)	0.57362 (13)	0.0490 (8)
C22	0.7303 (3)	0.36794 (16)	0.70832 (15)	0.0774 (10)
H1	0.51517	0.49729	0.09631	0.0598*
H2	0.31720	0.57886	0.02404	0.0743*
H3	0.30077	0.72999	0.04279	0.0822*
H4	0.48279	0.79915	0.13434	0.0816*
H5	0.67945	0.71831	0.21045	0.0635*
H7	0.81993	0.58569	0.24234	0.0473*
H8A	0.59930	0.53296	0.31232	0.0551*
H8B	0.57149	0.45413	0.24952	0.0551*
H10	0.79627	0.33561	0.24872	0.0481*
H11	1.03388	0.47245	0.24214	0.0465*
H13	1.27740	0.41420	0.19880	0.0700*
H14	1.42514	0.31870	0.12074	0.0909*
H15	1.29084	0.21721	0.03544	0.0981*
H16	1.00786	0.21087	0.02665	0.0952*
H17	0.86013	0.30759	0.10335	0.0690*
H18A	0.99136	0.58048	0.13174	0.0910*
H18B	0.84144	0.56824	0.06736	0.0910*
H18C	0.98595	0.49935	0.07109	0.0910*
H19A	1.08019	0.35618	0.35384	0.0869*
H19B	1.04053	0.27561	0.29462	0.0869*
H19C	0.93886	0.28981	0.37181	0.0869*
H20A	0.67918	0.55973	0.54619	0.0650*
H20B	0.85263	0.52040	0.53176	0.0650*
H22A	0.64140	0.33102	0.68696	0.1162*
H22B	0.70458	0.39208	0.76047	0.1162*
H22C	0.82870	0.33301	0.71532	0.1162*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0757 (11)	0.0737 (11)	0.0332 (8)	0.0271 (9)	0.0097 (7)	−0.0022 (7)
O2	0.0901 (12)	0.0665 (10)	0.0372 (9)	−0.0126 (9)	−0.0029 (8)	0.0039 (8)
O3	0.1051 (14)	0.0639 (11)	0.0629 (11)	−0.0216 (10)	0.0111 (10)	−0.0182 (9)
N1	0.0392 (9)	0.0444 (9)	0.0321 (9)	0.0053 (7)	0.0094 (8)	0.0040 (7)
N2	0.0561 (11)	0.0505 (10)	0.0343 (10)	0.0116 (9)	0.0086 (8)	−0.0057 (8)
C1	0.0560 (13)	0.0519 (13)	0.0414 (12)	0.0069 (11)	0.0010 (11)	0.0031 (10)
C2	0.0577 (14)	0.0802 (18)	0.0469 (14)	0.0085 (13)	−0.0040 (12)	0.0074 (13)
C3	0.0623 (16)	0.081 (2)	0.0624 (17)	0.0243 (14)	0.0081 (14)	0.0244 (14)
C4	0.0731 (17)	0.0438 (14)	0.090 (2)	0.0148 (13)	0.0279 (15)	0.0214 (14)
C5	0.0514 (13)	0.0458 (13)	0.0627 (15)	0.0006 (11)	0.0123 (12)	−0.0008 (11)
C6	0.0406 (11)	0.0401 (12)	0.0344 (11)	0.0043 (9)	0.0078 (9)	0.0030 (9)
C7	0.0425 (12)	0.0414 (11)	0.0346 (11)	0.0001 (9)	0.0043 (9)	−0.0041 (9)
C8	0.0427 (12)	0.0629 (14)	0.0328 (11)	0.0124 (10)	0.0071 (10)	0.0051 (10)
C9	0.0405 (11)	0.0458 (12)	0.0315 (11)	0.0015 (9)	0.0091 (9)	0.0032 (9)
C10	0.0438 (11)	0.0429 (12)	0.0342 (11)	0.0044 (9)	0.0065 (9)	−0.0005 (9)
C11	0.0350 (10)	0.0447 (11)	0.0365 (11)	−0.0002 (9)	0.0028 (9)	−0.0046 (9)
C12	0.0478 (13)	0.0468 (12)	0.0349 (11)	0.0055 (10)	0.0130 (10)	0.0030 (9)
C13	0.0483 (14)	0.0612 (15)	0.0672 (16)	0.0038 (11)	0.0174 (12)	0.0001 (12)
C14	0.0597 (16)	0.0826 (19)	0.088 (2)	0.0216 (14)	0.0294 (15)	0.0069 (16)
C15	0.099 (2)	0.079 (2)	0.0726 (19)	0.0311 (17)	0.0398 (17)	−0.0027 (16)
C16	0.101 (2)	0.0803 (19)	0.0580 (16)	0.0145 (16)	0.0181 (16)	−0.0243 (14)
C17	0.0589 (14)	0.0685 (16)	0.0455 (13)	0.0077 (12)	0.0061 (12)	−0.0092 (12)
C18	0.0643 (15)	0.0670 (16)	0.0537 (14)	0.0106 (12)	0.0265 (12)	0.0184 (12)
C19	0.0609 (14)	0.0614 (15)	0.0524 (14)	0.0172 (12)	0.0105 (12)	0.0028 (11)
C20	0.0788 (16)	0.0557 (14)	0.0283 (11)	0.0030 (12)	0.0058 (11)	−0.0052 (10)
C21	0.0581 (13)	0.0516 (14)	0.0383 (12)	0.0028 (12)	0.0107 (11)	−0.0102 (10)
C22	0.105 (2)	0.0694 (17)	0.0589 (16)	0.0111 (15)	0.0129 (15)	0.0156 (13)

Geometric parameters (Å, º) top

O1—N2	1.426 (2)	C20—C21	1.495 (3)
O1—C20	1.413 (2)	C1—H1	0.9300
O2—C21	1.339 (3)	C2—H2	0.9300
O2—C22	1.434 (3)	C3—H3	0.9300
O3—C21	1.185 (3)	C4—H4	0.9300
N1—C7	1.471 (2)	C5—H5	0.9300
N1—C11	1.469 (2)	C7—H7	0.9800
N1—C18	1.467 (3)	C8—H8A	0.9700
N2—C9	1.272 (2)	C8—H8B	0.9700
C1—C2	1.369 (3)	C10—H10	0.9800
C1—C6	1.383 (3)	C11—H11	0.9800
C2—C3	1.366 (4)	C13—H13	0.9300
C3—C4	1.355 (4)	C14—H14	0.9300
C4—C5	1.384 (3)	C15—H15	0.9300
C5—C6	1.381 (3)	C16—H16	0.9300
C6—C7	1.508 (2)	C17—H17	0.9300
C7—C8	1.527 (3)	C18—H18A	0.9600
C8—C9	1.486 (3)	C18—H18B	0.9600
C9—C10	1.490 (3)	C18—H18C	0.9600
C10—C11	1.542 (2)	C19—H19A	0.9600
C10—C19	1.511 (3)	C19—H19B	0.9600
C11—C12	1.514 (3)	C19—H19C	0.9600
C12—C13	1.371 (3)	C20—H20A	0.9700
C12—C17	1.388 (3)	C20—H20B	0.9700
C13—C14	1.388 (4)	C22—H22A	0.9600
C14—C15	1.362 (4)	C22—H22B	0.9600
C15—C16	1.376 (5)	C22—H22C	0.9600
C16—C17	1.383 (4)

N2—O1—C20	108.33 (15)	C6—C5—H5	120.00
C21—O2—C22	117.57 (18)	N1—C7—H7	108.00
C7—N1—C11	112.06 (14)	C6—C7—H7	108.00
C7—N1—C18	108.74 (15)	C8—C7—H7	108.00
C11—N1—C18	110.05 (15)	C7—C8—H8A	110.00
O1—N2—C9	109.98 (15)	C7—C8—H8B	110.00
C2—C1—C6	120.9 (2)	C9—C8—H8A	110.00
C1—C2—C3	120.5 (2)	C9—C8—H8B	110.00
C2—C3—C4	119.5 (2)	H8A—C8—H8B	108.00
C3—C4—C5	120.9 (2)	C9—C10—H10	107.00
C4—C5—C6	120.1 (2)	C11—C10—H10	107.00
C1—C6—C5	118.14 (18)	C19—C10—H10	107.00
C1—C6—C7	121.15 (17)	N1—C11—H11	108.00
C5—C6—C7	120.65 (17)	C10—C11—H11	108.00
N1—C7—C6	112.08 (14)	C12—C11—H11	108.00
N1—C7—C8	110.68 (15)	C12—C13—H13	119.00
C6—C7—C8	108.96 (14)	C14—C13—H13	119.00
C7—C8—C9	109.89 (14)	C13—C14—H14	120.00
N2—C9—C8	126.73 (17)	C15—C14—H14	120.00
N2—C9—C10	119.23 (16)	C14—C15—H15	120.00
C8—C9—C10	114.01 (15)	C16—C15—H15	120.00
C9—C10—C11	108.93 (15)	C15—C16—H16	120.00
C9—C10—C19	114.41 (16)	C17—C16—H16	120.00
C11—C10—C19	112.23 (15)	C12—C17—H17	120.00
N1—C11—C10	111.59 (13)	C16—C17—H17	120.00
N1—C11—C12	110.84 (15)	N1—C18—H18A	109.00
C10—C11—C12	110.65 (15)	N1—C18—H18B	109.00
C11—C12—C13	121.28 (18)	N1—C18—H18C	109.00
C11—C12—C17	120.5 (2)	H18A—C18—H18B	109.00
C13—C12—C17	118.2 (2)	H18A—C18—H18C	109.00
C12—C13—C14	121.2 (2)	H18B—C18—H18C	109.00
C13—C14—C15	119.9 (2)	C10—C19—H19A	109.00
C14—C15—C16	120.2 (3)	C10—C19—H19B	109.00
C15—C16—C17	119.7 (2)	C10—C19—H19C	109.00
C12—C17—C16	120.8 (2)	H19A—C19—H19B	109.00
O1—C20—C21	113.08 (17)	H19A—C19—H19C	109.00
O2—C21—O3	123.3 (2)	H19B—C19—H19C	109.00
O2—C21—C20	109.43 (18)	O1—C20—H20A	109.00
O3—C21—C20	127.2 (2)	O1—C20—H20B	109.00
C2—C1—H1	120.00	C21—C20—H20A	109.00
C6—C1—H1	120.00	C21—C20—H20B	109.00
C1—C2—H2	120.00	H20A—C20—H20B	108.00
C3—C2—H2	120.00	O2—C22—H22A	109.00
C2—C3—H3	120.00	O2—C22—H22B	109.00
C4—C3—H3	120.00	O2—C22—H22C	109.00
C3—C4—H4	120.00	H22A—C22—H22B	109.00
C5—C4—H4	120.00	H22A—C22—H22C	109.00
C4—C5—H5	120.00	H22B—C22—H22C	109.00

C20—O1—N2—C9	−172.81 (17)	C6—C7—C8—C9	178.85 (15)
N2—O1—C20—C21	−71.9 (2)	N1—C7—C8—C9	55.18 (19)
C22—O2—C21—C20	−179.44 (19)	C7—C8—C9—C10	−55.2 (2)
C22—O2—C21—O3	1.7 (3)	C7—C8—C9—N2	122.7 (2)
C18—N1—C11—C12	−57.7 (2)	N2—C9—C10—C11	−124.12 (18)
C7—N1—C11—C12	−178.86 (15)	N2—C9—C10—C19	2.4 (2)
C11—N1—C7—C6	−179.50 (14)	C8—C9—C10—C11	53.95 (19)
C18—N1—C7—C6	58.62 (19)	C8—C9—C10—C19	−179.55 (16)
C11—N1—C7—C8	−57.64 (18)	C19—C10—C11—C12	54.6 (2)
C18—N1—C11—C10	178.47 (15)	C9—C10—C11—C12	−177.68 (15)
C18—N1—C7—C8	−179.52 (15)	C19—C10—C11—N1	178.49 (15)
C7—N1—C11—C10	57.34 (18)	C9—C10—C11—N1	−53.77 (18)
O1—N2—C9—C8	3.3 (3)	C10—C11—C12—C17	66.3 (2)
O1—N2—C9—C10	−178.95 (15)	C10—C11—C12—C13	−110.6 (2)
C2—C1—C6—C7	176.48 (19)	N1—C11—C12—C17	−58.0 (2)
C6—C1—C2—C3	0.8 (3)	N1—C11—C12—C13	125.0 (2)
C2—C1—C6—C5	−0.6 (3)	C11—C12—C13—C14	177.3 (2)
C1—C2—C3—C4	−0.1 (4)	C13—C12—C17—C16	0.2 (3)
C2—C3—C4—C5	−0.8 (4)	C11—C12—C17—C16	−176.8 (2)
C3—C4—C5—C6	1.0 (4)	C17—C12—C13—C14	0.2 (3)
C4—C5—C6—C1	−0.3 (3)	C12—C13—C14—C15	−0.5 (4)
C4—C5—C6—C7	−177.4 (2)	C13—C14—C15—C16	0.2 (4)
C1—C6—C7—N1	51.3 (2)	C14—C15—C16—C17	0.2 (4)
C5—C6—C7—C8	105.5 (2)	C15—C16—C17—C12	−0.4 (4)
C5—C6—C7—N1	−131.70 (19)	O1—C20—C21—O3	−5.6 (4)
C1—C6—C7—C8	−71.5 (2)	O1—C20—C21—O2	175.58 (18)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.97	2.22	2.653 (2)	106
C22—H22A···O3	0.96	2.28	2.668 (3)	103
C22—H22B···Cg2ⁱ	0.96	2.76	3.525 (3)	138

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.97	2.22	2.653 (2)	106
C22—H22A···O3	0.96	2.28	2.668 (3)	103
C22—H22B···Cg2ⁱ	0.96	2.76	3.525 (3)	138

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The auther thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, India, for carrying out the data collection.

References

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

Methyl ({[(4E)-1,3-di­methyl-2,6-di­phenyl­piperidin-4-yl­­idene]amino}­­oxy)acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl ({[(4E)-1,3-dimethyl-2,6-diphenylpiperidin-4-ylidene]amino}oxy)acetate