Methyl ({[(4E)-1,3-dimethyl-2,6-di-phenyl-piperidin-4-yl-idene]amino}-oxy)acetate.

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 amino-oxy acetate group attached at the 4-position has an equatorial orientation. In the crystal, inversion dimers linked by pairs of C-H⋯π inter-actions occur.

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 = 366.45

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.214

S = 1.06

17582 reflections

249 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006667/rk2422sup1.cif

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

Click here for additional data file.

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

CCDC reference: 993682

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H26N2O3	F(000) = 784
Mr = 366.45	Dx = 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

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

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(Fo2) + (0.0418P)2 + 3.4429P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
17582 reflections	Δρmax = 0.31 e Å−3
249 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .