(E)-3-Methyl-2,6-di-phenyl-piperidin-4-one O-(3-methyl-benzo-yl)oxime.

In the title compound, C26H26N2O2, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C-H⋯O inter-actions connect the mol-ecules into zigzag chains along [001].

Related literature

For the biological activity of oxime esters, see: Crichlow et al. (2007 ▶); Hwu et al. (2008 ▶); Neely et al. (2013 ▶); Liu et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For comparable structures, see: Park et al. (2012a ▶,b ▶).

Experimental

Crystal data

C26H26N2O2

M = 398.49

Monoclinic,

a = 10.6265 (6) Å

b = 12.7146 (7) Å

c = 16.4031 (8) Å

β = 99.524 (2)°

V = 2185.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.977, T max = 0.985

37978 measured reflections

5367 independent reflections

3097 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.175

S = 1.04

5367 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016638/bt6984sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016638/bt6984Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016638/bt6984Isup3.cml

CCDC reference: 1005453

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

C26H26N2O2	F(000) = 848
Mr = 398.49	Dx = 1.211 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3910 reflections
a = 10.6265 (6) Å	θ = 2.0–28.3°
b = 12.7146 (7) Å	µ = 0.08 mm−1
c = 16.4031 (8) Å	T = 293 K
β = 99.524 (2)°	Block, colourless
V = 2185.7 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5367 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω & φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.977, Tmax = 0.985	k = −16→16
37978 measured reflections	l = −21→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.070P)2 + 0.8065P] where P = (Fo2 + 2Fc2)/3
5367 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
H1A	0.018 (2)	1.0450 (18)	0.1578 (13)	0.061 (7)*
O1	0.02902 (16)	0.61978 (10)	0.21324 (9)	0.0619 (4)
O2	−0.06469 (18)	0.49464 (12)	0.27901 (11)	0.0731 (5)
N1	0.04764 (16)	0.99163 (12)	0.18907 (10)	0.0436 (4)
C11	−0.04007 (18)	0.97408 (14)	0.24813 (11)	0.0440 (4)
H11	−0.1257	0.9608	0.2172	0.053*
N2	−0.01386 (18)	0.69687 (13)	0.26740 (11)	0.0564 (5)
C20	0.05405 (18)	0.44768 (15)	0.17305 (12)	0.0456 (4)
C10	0.0019 (2)	0.87831 (15)	0.30293 (12)	0.0515 (5)
H10	0.0828	0.8974	0.3378	0.062*
C7	0.05728 (18)	0.90311 (15)	0.13409 (11)	0.0446 (4)
H7	−0.0282	0.8857	0.1047	0.054*
C6	0.14265 (18)	0.92717 (15)	0.07160 (11)	0.0459 (5)
C9	0.0297 (2)	0.78632 (15)	0.25099 (12)	0.0480 (5)
C12	−0.04334 (19)	1.07383 (15)	0.29832 (11)	0.0445 (4)
C19	−0.00232 (19)	0.51999 (15)	0.22822 (12)	0.0478 (5)
C25	0.10773 (19)	0.48317 (16)	0.10675 (12)	0.0500 (5)
H25	0.1056	0.5547	0.0946	0.060*
C24	0.1646 (2)	0.41475 (18)	0.05806 (13)	0.0563 (5)
C13	−0.1543 (2)	1.13041 (16)	0.29641 (12)	0.0511 (5)
H13	−0.2295	1.1070	0.2643	0.061*
C8	0.1099 (2)	0.80955 (16)	0.18605 (14)	0.0562 (5)
H8A	0.1115	0.7485	0.1508	0.067*
H8B	0.1968	0.8243	0.2123	0.067*
C14	−0.1543 (3)	1.22239 (18)	0.34226 (15)	0.0652 (6)
H14	−0.2294	1.2607	0.3400	0.078*
C15	−0.0451 (3)	1.25700 (18)	0.39050 (15)	0.0694 (7)
H15	−0.0463	1.3177	0.4219	0.083*
C17	0.0669 (2)	1.11168 (17)	0.34612 (14)	0.0606 (6)
H17	0.1433	1.0756	0.3471	0.073*
C16	0.0654 (3)	1.20238 (19)	0.39244 (15)	0.0703 (7)
H16	0.1400	1.2261	0.4250	0.084*
C1	0.2413 (2)	0.99896 (18)	0.08749 (15)	0.0611 (6)
H1	0.2542	1.0365	0.1368	0.073*
C18	−0.0920 (3)	0.85368 (19)	0.36119 (16)	0.0790 (8)
H18A	−0.1044	0.9153	0.3928	0.119*
H18B	−0.0587	0.7979	0.3979	0.119*
H18C	−0.1721	0.8324	0.3295	0.119*
C22	0.1156 (3)	0.27329 (18)	0.14423 (17)	0.0735 (7)
H22	0.1193	0.2019	0.1569	0.088*
C21	0.0567 (2)	0.34152 (16)	0.19135 (15)	0.0590 (6)
H21	0.0192	0.3164	0.2349	0.071*
C23	0.1689 (2)	0.30943 (19)	0.07893 (16)	0.0698 (7)
H23	0.2086	0.2622	0.0481	0.084*
C5	0.1289 (2)	0.87079 (19)	−0.00125 (13)	0.0608 (6)
H5	0.0640	0.8213	−0.0126	0.073*
C4	0.2102 (3)	0.8869 (2)	−0.05753 (14)	0.0768 (8)
H4	0.1998	0.8479	−0.1062	0.092*
C2	0.3212 (3)	1.0150 (2)	0.0298 (2)	0.0838 (8)
H2	0.3864	1.0644	0.0405	0.101*
C3	0.3058 (3)	0.9595 (3)	−0.04244 (18)	0.0880 (9)
H3	0.3597	0.9711	−0.0808	0.106*
C26	0.2245 (3)	0.4555 (3)	−0.01269 (15)	0.0841 (8)
H26A	0.2596	0.3978	−0.0393	0.126*
H26B	0.2912	0.5043	0.0079	0.126*
H26C	0.1609	0.4904	−0.0518	0.126*

	U11	U22	U33	U12	U13	U23
O1	0.0913 (11)	0.0369 (7)	0.0691 (9)	−0.0054 (7)	0.0472 (8)	−0.0056 (7)
O2	0.0998 (13)	0.0492 (9)	0.0847 (11)	0.0049 (8)	0.0569 (10)	0.0115 (8)
N1	0.0528 (10)	0.0380 (8)	0.0433 (9)	0.0039 (7)	0.0178 (7)	0.0007 (7)
C11	0.0469 (11)	0.0431 (10)	0.0446 (10)	−0.0001 (8)	0.0154 (8)	−0.0039 (8)
N2	0.0797 (12)	0.0400 (9)	0.0575 (10)	0.0013 (8)	0.0349 (9)	−0.0037 (8)
C20	0.0474 (11)	0.0413 (10)	0.0487 (11)	−0.0028 (8)	0.0102 (9)	−0.0016 (8)
C10	0.0714 (14)	0.0422 (10)	0.0452 (11)	0.0007 (9)	0.0221 (10)	0.0006 (8)
C7	0.0484 (11)	0.0440 (10)	0.0445 (10)	−0.0022 (8)	0.0166 (8)	−0.0035 (8)
C6	0.0493 (11)	0.0487 (11)	0.0420 (10)	0.0070 (9)	0.0145 (8)	0.0073 (8)
C9	0.0611 (12)	0.0387 (10)	0.0486 (11)	0.0028 (9)	0.0217 (9)	0.0021 (8)
C12	0.0528 (11)	0.0408 (10)	0.0429 (10)	0.0008 (8)	0.0169 (9)	−0.0015 (8)
C19	0.0561 (12)	0.0395 (10)	0.0508 (11)	0.0021 (9)	0.0177 (9)	0.0052 (8)
C25	0.0560 (12)	0.0471 (11)	0.0486 (11)	−0.0020 (9)	0.0136 (9)	−0.0011 (9)
C24	0.0520 (12)	0.0665 (14)	0.0519 (12)	−0.0056 (10)	0.0131 (9)	−0.0136 (10)
C13	0.0547 (12)	0.0510 (12)	0.0519 (11)	0.0030 (9)	0.0214 (9)	0.0016 (9)
C8	0.0706 (14)	0.0422 (11)	0.0638 (13)	0.0050 (10)	0.0350 (11)	0.0044 (9)
C14	0.0804 (17)	0.0522 (13)	0.0720 (15)	0.0162 (12)	0.0390 (13)	0.0023 (11)
C15	0.106 (2)	0.0467 (12)	0.0627 (14)	−0.0041 (13)	0.0359 (14)	−0.0135 (11)
C17	0.0611 (14)	0.0520 (12)	0.0677 (14)	0.0033 (10)	0.0084 (11)	−0.0089 (10)
C16	0.0871 (18)	0.0604 (14)	0.0627 (14)	−0.0126 (13)	0.0103 (13)	−0.0135 (11)
C1	0.0604 (14)	0.0604 (13)	0.0679 (14)	−0.0016 (11)	0.0267 (11)	0.0030 (11)
C18	0.127 (2)	0.0534 (14)	0.0716 (16)	0.0007 (14)	0.0616 (16)	0.0000 (11)
C22	0.0898 (18)	0.0391 (12)	0.0947 (19)	−0.0051 (12)	0.0247 (15)	−0.0114 (12)
C21	0.0699 (14)	0.0406 (11)	0.0693 (14)	−0.0073 (10)	0.0192 (11)	−0.0018 (10)
C23	0.0723 (15)	0.0579 (14)	0.0811 (17)	−0.0024 (12)	0.0180 (13)	−0.0283 (12)
C5	0.0667 (14)	0.0741 (15)	0.0440 (11)	0.0095 (11)	0.0158 (10)	−0.0007 (10)
C4	0.0833 (18)	0.108 (2)	0.0433 (12)	0.0332 (17)	0.0227 (12)	0.0103 (13)
C2	0.0679 (16)	0.0896 (19)	0.103 (2)	−0.0024 (14)	0.0420 (15)	0.0255 (17)
C3	0.085 (2)	0.117 (2)	0.0742 (18)	0.0317 (18)	0.0482 (15)	0.0371 (17)
C26	0.0888 (19)	0.110 (2)	0.0610 (15)	0.0015 (16)	0.0345 (14)	−0.0119 (14)

O1—C19	1.345 (2)	C8—H8A	0.9700
O1—N2	1.446 (2)	C8—H8B	0.9700
O2—C19	1.192 (2)	C14—C15	1.364 (4)
N1—C7	1.456 (2)	C14—H14	0.9300
N1—C11	1.468 (2)	C15—C16	1.360 (4)
N1—H1A	0.88 (2)	C15—H15	0.9300
C11—C12	1.516 (2)	C17—C16	1.383 (3)
C11—C10	1.535 (3)	C17—H17	0.9300
C11—H11	0.9800	C16—H16	0.9300
N2—C9	1.273 (2)	C1—C2	1.387 (3)
C20—C21	1.382 (3)	C1—H1	0.9300
C20—C25	1.384 (3)	C18—H18A	0.9600
C20—C19	1.484 (3)	C18—H18B	0.9600
C10—C9	1.505 (3)	C18—H18C	0.9600
C10—C18	1.524 (3)	C22—C23	1.371 (3)
C10—H10	0.9800	C22—C21	1.379 (3)
C7—C6	1.508 (2)	C22—H22	0.9300
C7—C8	1.516 (3)	C21—H21	0.9300
C7—H7	0.9800	C23—H23	0.9300
C6—C5	1.380 (3)	C5—C4	1.380 (3)
C6—C1	1.382 (3)	C5—H5	0.9300
C9—C8	1.500 (3)	C4—C3	1.365 (4)
C12—C13	1.377 (3)	C4—H4	0.9300
C12—C17	1.384 (3)	C2—C3	1.366 (4)
C25—C24	1.386 (3)	C2—H2	0.9300
C25—H25	0.9300	C3—H3	0.9300
C24—C23	1.381 (3)	C26—H26A	0.9600
C24—C26	1.505 (3)	C26—H26B	0.9600
C13—C14	1.390 (3)	C26—H26C	0.9600
C13—H13	0.9300
C19—O1—N2	114.49 (14)	C7—C8—H8B	109.5
C7—N1—C11	114.11 (15)	H8A—C8—H8B	108.1
C7—N1—H1A	106.9 (14)	C15—C14—C13	120.6 (2)
C11—N1—H1A	107.4 (14)	C15—C14—H14	119.7
N1—C11—C12	107.78 (15)	C13—C14—H14	119.7
N1—C11—C10	110.62 (15)	C16—C15—C14	119.8 (2)
C12—C11—C10	112.10 (15)	C16—C15—H15	120.1
N1—C11—H11	108.8	C14—C15—H15	120.1
C12—C11—H11	108.8	C16—C17—C12	121.0 (2)
C10—C11—H11	108.8	C16—C17—H17	119.5
C9—N2—O1	108.23 (15)	C12—C17—H17	119.5
C21—C20—C25	119.53 (19)	C15—C16—C17	120.1 (2)
C21—C20—C19	117.92 (18)	C15—C16—H16	119.9
C25—C20—C19	122.50 (17)	C17—C16—H16	119.9
C9—C10—C18	113.92 (17)	C6—C1—C2	120.0 (2)
C9—C10—C11	110.50 (15)	C6—C1—H1	120.0
C18—C10—C11	111.89 (18)	C2—C1—H1	120.0
C9—C10—H10	106.7	C10—C18—H18A	109.5
C18—C10—H10	106.7	C10—C18—H18B	109.5
C11—C10—H10	106.7	H18A—C18—H18B	109.5
N1—C7—C6	112.08 (16)	C10—C18—H18C	109.5
N1—C7—C8	108.40 (16)	H18A—C18—H18C	109.5
C6—C7—C8	109.50 (15)	H18B—C18—H18C	109.5
N1—C7—H7	108.9	C23—C22—C21	120.8 (2)
C6—C7—H7	108.9	C23—C22—H22	119.6
C8—C7—H7	108.9	C21—C22—H22	119.6
C5—C6—C1	118.31 (19)	C22—C21—C20	119.2 (2)
C5—C6—C7	119.59 (19)	C22—C21—H21	120.4
C1—C6—C7	121.92 (18)	C20—C21—H21	120.4
N2—C9—C8	126.54 (17)	C22—C23—C24	121.2 (2)
N2—C9—C10	117.54 (17)	C22—C23—H23	119.4
C8—C9—C10	115.90 (16)	C24—C23—H23	119.4
C13—C12—C17	118.20 (19)	C4—C5—C6	120.9 (2)
C13—C12—C11	121.42 (18)	C4—C5—H5	119.5
C17—C12—C11	120.36 (18)	C6—C5—H5	119.5
O2—C19—O1	124.49 (18)	C3—C4—C5	120.6 (3)
O2—C19—C20	125.87 (18)	C3—C4—H4	119.7
O1—C19—C20	109.63 (15)	C5—C4—H4	119.7
C20—C25—C24	121.6 (2)	C3—C2—C1	121.1 (3)
C20—C25—H25	119.2	C3—C2—H2	119.4
C24—C25—H25	119.2	C1—C2—H2	119.4
C23—C24—C25	117.7 (2)	C4—C3—C2	119.0 (2)
C23—C24—C26	121.6 (2)	C4—C3—H3	120.5
C25—C24—C26	120.6 (2)	C2—C3—H3	120.5
C12—C13—C14	120.3 (2)	C24—C26—H26A	109.5
C12—C13—H13	119.9	C24—C26—H26B	109.5
C14—C13—H13	119.9	H26A—C26—H26B	109.5
C9—C8—C7	110.72 (16)	C24—C26—H26C	109.5
C9—C8—H8A	109.5	H26A—C26—H26C	109.5
C7—C8—H8A	109.5	H26B—C26—H26C	109.5
C9—C8—H8B	109.5
C7—N1—C11—C12	−177.94 (16)	C19—C20—C25—C24	177.28 (19)
C7—N1—C11—C10	59.2 (2)	C20—C25—C24—C23	−1.5 (3)
C19—O1—N2—C9	175.23 (19)	C20—C25—C24—C26	−178.8 (2)
N1—C11—C10—C9	−48.2 (2)	C17—C12—C13—C14	−0.6 (3)
C12—C11—C10—C9	−168.54 (16)	C11—C12—C13—C14	−179.19 (17)
N1—C11—C10—C18	−176.30 (18)	N2—C9—C8—C7	131.3 (2)
C12—C11—C10—C18	63.4 (2)	C10—C9—C8—C7	−50.5 (3)
C11—N1—C7—C6	176.81 (16)	N1—C7—C8—C9	55.3 (2)
C11—N1—C7—C8	−62.2 (2)	C6—C7—C8—C9	177.81 (17)
N1—C7—C6—C5	−157.34 (18)	C12—C13—C14—C15	−0.9 (3)
C8—C7—C6—C5	82.3 (2)	C13—C14—C15—C16	1.4 (3)
N1—C7—C6—C1	27.6 (3)	C13—C12—C17—C16	1.6 (3)
C8—C7—C6—C1	−92.7 (2)	C11—C12—C17—C16	−179.80 (19)
O1—N2—C9—C8	0.9 (3)	C14—C15—C16—C17	−0.4 (4)
O1—N2—C9—C10	−177.23 (17)	C12—C17—C16—C15	−1.1 (4)
C18—C10—C9—N2	−8.3 (3)	C5—C6—C1—C2	1.9 (3)
C11—C10—C9—N2	−135.2 (2)	C7—C6—C1—C2	177.0 (2)
C18—C10—C9—C8	173.4 (2)	C23—C22—C21—C20	−1.3 (4)
C11—C10—C9—C8	46.4 (3)	C25—C20—C21—C22	1.6 (3)
N1—C11—C12—C13	117.95 (19)	C19—C20—C21—C22	−176.0 (2)
C10—C11—C12—C13	−120.1 (2)	C21—C22—C23—C24	−0.4 (4)
N1—C11—C12—C17	−60.6 (2)	C25—C24—C23—C22	1.7 (4)
C10—C11—C12—C17	61.4 (2)	C26—C24—C23—C22	179.1 (2)
N2—O1—C19—O2	3.1 (3)	C1—C6—C5—C4	−1.1 (3)
N2—O1—C19—C20	−176.11 (16)	C7—C6—C5—C4	−176.3 (2)
C21—C20—C19—O2	−13.2 (3)	C6—C5—C4—C3	−0.3 (4)
C25—C20—C19—O2	169.3 (2)	C6—C1—C2—C3	−1.2 (4)
C21—C20—C19—O1	165.91 (19)	C5—C4—C3—C2	1.0 (4)
C25—C20—C19—O1	−11.5 (3)	C1—C2—C3—C4	−0.3 (4)
C21—C20—C25—C24	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.59	3.485 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.59	3.485 (3)	160

Symmetry code: (i) .