(E)-1,3-Dimethyl-2,6-di-phenyl-piperidin-4-one O-(phen-oxy-carbon-yl)oxime.

The title piperidine derivative, C26H26N2O3, has an E conformation about the N=C bond. The piperidine ring has a chair conformation and its mean plane is almost perpendicular to the attached phenyl rings, making dihedral angles of 87.47 (9) and 87.34 (8)°. The planes of these two phenyl rings are inclined to one another by 60.38 (9)°. The plane of the terminal phenyl ring is tilted at an angle of 32.79 (9)° to the mean plane of the piperidine ring. The mol-ecular conformation is stabilized by two intra-molecular C-H⋯O contacts. There are no significant inter-molecular inter-actions in the crystal.

Related literature

For the biological activity of piperidine derivatives, see, for example: Moldt et al. (1997 ▶); Peters et al. (2009 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C26H26N2O3

M = 414.49

Monoclinic,

a = 16.2004 (12) Å

b = 11.9587 (10) Å

c = 11.3601 (7) Å

β = 102.547 (2)°

V = 2148.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T min = 0.979, T max = 0.983

27566 measured reflections

6686 independent reflections

3950 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.180

S = 1.01

6686 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2/SAINT (Bruker, 2004 ▶); data reduction: SAINT/XPREP ; 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010526/su2678sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010526/su2678Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010526/su2678Isup3.cml

CCDC reference: 1001814

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

C26H26N2O3	F(000) = 880
Mr = 414.49	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8834 reflections
a = 16.2004 (12) Å	θ = 2.1–31.2°
b = 11.9587 (10) Å	µ = 0.08 mm−1
c = 11.3601 (7) Å	T = 293 K
β = 102.547 (2)°	Block, colourless
V = 2148.3 (3) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	6686 independent reflections
Radiation source: fine-focus sealed tube	3950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scan	θmax = 30.8°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −23→21
Tmin = 0.979, Tmax = 0.983	k = −17→17
27566 measured reflections	l = −16→16

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) = 0.180	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.093P)2 + 0.2301P] where P = (Fo2 + 2Fc2)/3
6686 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.35 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
C2	0.16989 (9)	0.35382 (12)	0.83490 (12)	0.0379 (3)
H2	0.1382	0.2997	0.8726	0.045*
C3	0.26100 (11)	0.31168 (15)	0.85152 (13)	0.0467 (4)
H3A	0.2608	0.2355	0.8220	0.056*
H3B	0.2915	0.3579	0.8051	0.056*
C4	0.30428 (9)	0.31542 (13)	0.98144 (13)	0.0393 (3)
C5	0.30006 (9)	0.42707 (12)	1.03942 (13)	0.0389 (3)
H5	0.3253	0.4815	0.9933	0.047*
C6	0.20588 (9)	0.45817 (12)	1.02319 (12)	0.0368 (3)
H6	0.1778	0.3995	1.0603	0.044*
C7	0.19662 (9)	0.56761 (13)	1.08548 (12)	0.0382 (3)
C8	0.15971 (11)	0.57068 (15)	1.18468 (14)	0.0505 (4)
H8	0.1385	0.5053	1.2112	0.061*
C9	0.15411 (12)	0.67029 (18)	1.24476 (15)	0.0590 (5)
H9	0.1293	0.6711	1.3113	0.071*
C10	0.18471 (12)	0.76735 (16)	1.20726 (15)	0.0565 (5)
H10	0.1806	0.8340	1.2477	0.068*
C11	0.22174 (12)	0.76556 (15)	1.10914 (16)	0.0529 (4)
H11	0.2430	0.8312	1.0833	0.064*
C12	0.22743 (11)	0.66632 (14)	1.04893 (14)	0.0455 (4)
H12	0.2525	0.6661	0.9826	0.055*
C13	0.12923 (10)	0.35957 (13)	0.70176 (12)	0.0399 (3)
C14	0.16171 (12)	0.42803 (15)	0.62530 (14)	0.0509 (4)
H14	0.2105	0.4692	0.6550	0.061*
C15	0.12225 (15)	0.43587 (17)	0.50478 (15)	0.0654 (6)
H15	0.1445	0.4822	0.4537	0.078*
C16	0.05001 (15)	0.37504 (19)	0.46032 (16)	0.0700 (6)
H16	0.0228	0.3817	0.3796	0.084*
C17	0.01834 (14)	0.30530 (19)	0.53423 (18)	0.0689 (6)
H17	−0.0298	0.2630	0.5038	0.083*
C18	0.05790 (12)	0.29753 (16)	0.65455 (16)	0.0545 (4)
H18	0.0361	0.2496	0.7047	0.065*
C19	0.34923 (12)	0.43356 (15)	1.16909 (15)	0.0546 (4)
H19A	0.3214	0.3891	1.2193	0.082*
H19B	0.3519	0.5099	1.1958	0.082*
H19C	0.4055	0.4058	1.1743	0.082*
C20	0.37323 (10)	0.05039 (13)	1.04333 (14)	0.0445 (4)
C21	0.41582 (10)	−0.13514 (13)	1.00076 (14)	0.0446 (4)
C22	0.39797 (12)	−0.21341 (15)	0.91128 (15)	0.0534 (4)
H22	0.3654	−0.1951	0.8358	0.064*
C23	0.42925 (14)	−0.32043 (16)	0.93527 (19)	0.0640 (5)
H23	0.4181	−0.3746	0.8752	0.077*
C24	0.47672 (13)	−0.34739 (16)	1.04712 (19)	0.0619 (5)
H24	0.4969	−0.4199	1.0630	0.074*
C25	0.49410 (13)	−0.26815 (16)	1.13426 (18)	0.0622 (5)
H25	0.5262	−0.2866	1.2100	0.075*
C26	0.46459 (12)	−0.16009 (15)	1.11162 (16)	0.0587 (5)
H26	0.4777	−0.1053	1.1708	0.070*
C27	0.07667 (10)	0.49575 (17)	0.87840 (15)	0.0533 (4)
H27A	0.0505	0.4981	0.7941	0.080*
H27B	0.0732	0.5682	0.9134	0.080*
H27C	0.0480	0.4420	0.9180	0.080*
N1	0.16563 (7)	0.46358 (10)	0.89327 (10)	0.0357 (3)
N2	0.34143 (8)	0.23699 (11)	1.04748 (11)	0.0438 (3)
O1	0.34161 (8)	0.13746 (10)	0.97534 (9)	0.0528 (3)
O2	0.38576 (11)	0.04349 (12)	1.14880 (12)	0.0795 (5)
O3	0.38400 (9)	−0.02830 (10)	0.96515 (10)	0.0643 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0455 (8)	0.0346 (7)	0.0319 (6)	0.0009 (6)	0.0048 (6)	0.0017 (5)
C3	0.0558 (10)	0.0460 (9)	0.0356 (7)	0.0169 (7)	0.0042 (6)	0.0000 (6)
C4	0.0394 (7)	0.0390 (8)	0.0379 (7)	0.0063 (6)	0.0054 (6)	0.0017 (6)
C5	0.0430 (8)	0.0345 (7)	0.0369 (7)	0.0018 (6)	0.0035 (6)	0.0030 (6)
C6	0.0432 (8)	0.0374 (8)	0.0297 (6)	0.0003 (6)	0.0077 (5)	0.0022 (5)
C7	0.0403 (8)	0.0421 (8)	0.0315 (6)	0.0047 (6)	0.0061 (5)	−0.0001 (6)
C8	0.0569 (10)	0.0568 (11)	0.0406 (8)	−0.0011 (8)	0.0171 (7)	−0.0023 (7)
C9	0.0672 (12)	0.0733 (13)	0.0403 (8)	0.0103 (10)	0.0200 (8)	−0.0092 (8)
C10	0.0633 (11)	0.0537 (11)	0.0486 (9)	0.0150 (9)	0.0039 (8)	−0.0141 (8)
C11	0.0594 (10)	0.0407 (9)	0.0575 (10)	0.0038 (8)	0.0101 (8)	−0.0021 (7)
C12	0.0530 (9)	0.0439 (9)	0.0417 (8)	0.0065 (7)	0.0147 (7)	0.0011 (7)
C13	0.0472 (8)	0.0369 (8)	0.0330 (6)	0.0077 (6)	0.0033 (6)	−0.0026 (6)
C14	0.0631 (11)	0.0490 (10)	0.0403 (8)	0.0061 (8)	0.0106 (7)	0.0045 (7)
C15	0.0961 (16)	0.0622 (12)	0.0386 (8)	0.0197 (11)	0.0164 (9)	0.0081 (8)
C16	0.0919 (15)	0.0724 (14)	0.0355 (8)	0.0366 (12)	−0.0086 (9)	−0.0114 (9)
C17	0.0645 (12)	0.0750 (14)	0.0556 (11)	0.0092 (10)	−0.0126 (9)	−0.0179 (10)
C18	0.0552 (10)	0.0560 (11)	0.0483 (9)	−0.0004 (8)	0.0024 (7)	−0.0042 (8)
C19	0.0599 (10)	0.0488 (10)	0.0455 (8)	0.0038 (8)	−0.0094 (7)	−0.0011 (7)
C20	0.0463 (9)	0.0403 (8)	0.0439 (8)	0.0077 (7)	0.0033 (6)	0.0008 (6)
C21	0.0487 (9)	0.0367 (8)	0.0461 (8)	0.0044 (7)	0.0051 (7)	0.0002 (7)
C22	0.0631 (11)	0.0483 (10)	0.0477 (9)	0.0000 (8)	0.0097 (8)	−0.0060 (8)
C23	0.0785 (13)	0.0450 (10)	0.0721 (12)	−0.0025 (9)	0.0240 (10)	−0.0132 (9)
C24	0.0689 (12)	0.0390 (9)	0.0833 (14)	0.0092 (9)	0.0283 (10)	0.0044 (9)
C25	0.0678 (12)	0.0529 (11)	0.0615 (11)	0.0182 (9)	0.0044 (9)	0.0091 (9)
C26	0.0675 (11)	0.0477 (10)	0.0521 (9)	0.0146 (8)	−0.0066 (8)	−0.0046 (8)
C27	0.0437 (9)	0.0664 (12)	0.0465 (9)	0.0141 (8)	0.0029 (7)	−0.0087 (8)
N1	0.0373 (6)	0.0380 (6)	0.0306 (5)	0.0054 (5)	0.0046 (4)	−0.0008 (5)
N2	0.0496 (7)	0.0368 (7)	0.0420 (7)	0.0081 (6)	0.0037 (5)	−0.0018 (5)
O1	0.0691 (8)	0.0402 (6)	0.0433 (6)	0.0174 (6)	−0.0004 (5)	0.0004 (5)
O2	0.1305 (14)	0.0596 (9)	0.0476 (7)	0.0390 (9)	0.0178 (8)	0.0083 (6)
O3	0.0964 (10)	0.0428 (7)	0.0440 (6)	0.0213 (7)	−0.0060 (6)	−0.0031 (5)

C2—N1	1.4790 (18)	C15—C16	1.377 (3)
C2—C13	1.5144 (18)	C15—H15	0.9300
C2—C3	1.532 (2)	C16—C17	1.360 (3)
C2—H2	0.9800	C16—H16	0.9300
C3—C4	1.491 (2)	C17—C18	1.381 (2)
C3—H3A	0.9700	C17—H17	0.9300
C3—H3B	0.9700	C18—H18	0.9300
C4—N2	1.2683 (19)	C19—H19A	0.9600
C4—C5	1.497 (2)	C19—H19B	0.9600
C5—C19	1.517 (2)	C19—H19C	0.9600
C5—C6	1.542 (2)	C20—O2	1.1738 (19)
C5—H5	0.9800	C20—O1	1.3310 (18)
C6—N1	1.4797 (17)	C20—O3	1.3312 (19)
C6—C7	1.511 (2)	C21—C22	1.366 (2)
C6—H6	0.9800	C21—C26	1.366 (2)
C7—C12	1.380 (2)	C21—O3	1.4040 (19)
C7—C8	1.386 (2)	C22—C23	1.382 (3)
C8—C9	1.386 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.373 (3)
C9—C10	1.366 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.355 (3)
C10—C11	1.376 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.382 (2)
C11—C12	1.383 (2)	C25—H25	0.9300
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—N1	1.4655 (19)
C13—C14	1.378 (2)	C27—H27A	0.9600
C13—C18	1.380 (2)	C27—H27B	0.9600
C14—C15	1.383 (2)	C27—H27C	0.9600
C14—H14	0.9300	N2—O1	1.4454 (16)
N1—C2—C13	110.79 (11)	C16—C15—C14	120.03 (19)
N1—C2—C3	111.98 (12)	C16—C15—H15	120.0
C13—C2—C3	109.65 (12)	C14—C15—H15	120.0
N1—C2—H2	108.1	C17—C16—C15	120.12 (16)
C13—C2—H2	108.1	C17—C16—H16	119.9
C3—C2—H2	108.1	C15—C16—H16	119.9
C4—C3—C2	110.21 (12)	C16—C17—C18	119.7 (2)
C4—C3—H3A	109.6	C16—C17—H17	120.1
C2—C3—H3A	109.6	C18—C17—H17	120.1
C4—C3—H3B	109.6	C13—C18—C17	121.20 (19)
C2—C3—H3B	109.6	C13—C18—H18	119.4
H3A—C3—H3B	108.1	C17—C18—H18	119.4
N2—C4—C3	128.62 (14)	C5—C19—H19A	109.5
N2—C4—C5	117.42 (13)	C5—C19—H19B	109.5
C3—C4—C5	113.94 (12)	H19A—C19—H19B	109.5
C4—C5—C19	114.10 (12)	C5—C19—H19C	109.5
C4—C5—C6	107.53 (12)	H19A—C19—H19C	109.5
C19—C5—C6	113.64 (13)	H19B—C19—H19C	109.5
C4—C5—H5	107.1	O2—C20—O1	127.35 (15)
C19—C5—H5	107.1	O2—C20—O3	127.78 (15)
C6—C5—H5	107.1	O1—C20—O3	104.81 (13)
N1—C6—C7	111.23 (11)	C22—C21—C26	121.53 (16)
N1—C6—C5	109.87 (11)	C22—C21—O3	113.84 (14)
C7—C6—C5	110.45 (12)	C26—C21—O3	124.53 (15)
N1—C6—H6	108.4	C21—C22—C23	118.60 (17)
C7—C6—H6	108.4	C21—C22—H22	120.7
C5—C6—H6	108.4	C23—C22—H22	120.7
C12—C7—C8	118.03 (14)	C24—C23—C22	120.51 (18)
C12—C7—C6	121.39 (13)	C24—C23—H23	119.7
C8—C7—C6	120.53 (14)	C22—C23—H23	119.7
C9—C8—C7	120.60 (17)	C25—C24—C23	119.84 (18)
C9—C8—H8	119.7	C25—C24—H24	120.1
C7—C8—H8	119.7	C23—C24—H24	120.1
C10—C9—C8	120.66 (16)	C24—C25—C26	120.61 (18)
C10—C9—H9	119.7	C24—C25—H25	119.7
C8—C9—H9	119.7	C26—C25—H25	119.7
C9—C10—C11	119.40 (16)	C21—C26—C25	118.88 (17)
C9—C10—H10	120.3	C21—C26—H26	120.6
C11—C10—H10	120.3	C25—C26—H26	120.6
C10—C11—C12	120.11 (17)	N1—C27—H27A	109.5
C10—C11—H11	119.9	N1—C27—H27B	109.5
C12—C11—H11	119.9	H27A—C27—H27B	109.5
C7—C12—C11	121.19 (15)	N1—C27—H27C	109.5
C7—C12—H12	119.4	H27A—C27—H27C	109.5
C11—C12—H12	119.4	H27B—C27—H27C	109.5
C14—C13—C18	118.45 (14)	C27—N1—C2	108.77 (12)
C14—C13—C2	120.91 (14)	C27—N1—C6	109.62 (11)
C18—C13—C2	120.63 (14)	C2—N1—C6	110.79 (11)
C13—C14—C15	120.44 (18)	C4—N2—O1	109.43 (11)
C13—C14—H14	119.8	C20—O1—N2	111.29 (11)
C15—C14—H14	119.8	C20—O3—C21	122.97 (13)
N1—C2—C3—C4	51.47 (17)	C14—C15—C16—C17	−1.4 (3)
C13—C2—C3—C4	174.87 (13)	C15—C16—C17—C18	1.4 (3)
C2—C3—C4—N2	125.06 (18)	C14—C13—C18—C17	−1.5 (3)
C2—C3—C4—C5	−53.16 (18)	C2—C13—C18—C17	177.48 (16)
N2—C4—C5—C19	5.7 (2)	C16—C17—C18—C13	0.1 (3)
C3—C4—C5—C19	−175.91 (14)	C26—C21—C22—C23	1.0 (3)
N2—C4—C5—C6	−121.35 (15)	O3—C21—C22—C23	177.45 (17)
C3—C4—C5—C6	57.08 (16)	C21—C22—C23—C24	0.5 (3)
C4—C5—C6—N1	−59.89 (15)	C22—C23—C24—C25	−0.9 (3)
C19—C5—C6—N1	172.82 (12)	C23—C24—C25—C26	−0.1 (3)
C4—C5—C6—C7	177.03 (11)	C22—C21—C26—C25	−2.1 (3)
C19—C5—C6—C7	49.75 (17)	O3—C21—C26—C25	−178.08 (19)
N1—C6—C7—C12	−58.45 (18)	C24—C25—C26—C21	1.6 (3)
C5—C6—C7—C12	63.83 (17)	C13—C2—N1—C27	59.84 (15)
N1—C6—C7—C8	124.20 (15)	C3—C2—N1—C27	−177.40 (12)
C5—C6—C7—C8	−113.52 (15)	C13—C2—N1—C6	−179.61 (12)
C12—C7—C8—C9	0.1 (2)	C3—C2—N1—C6	−56.85 (15)
C6—C7—C8—C9	177.50 (15)	C7—C6—N1—C27	−56.06 (16)
C7—C8—C9—C10	0.1 (3)	C5—C6—N1—C27	−178.67 (13)
C8—C9—C10—C11	−0.3 (3)	C7—C6—N1—C2	−176.10 (12)
C9—C10—C11—C12	0.3 (3)	C5—C6—N1—C2	61.28 (15)
C8—C7—C12—C11	0.0 (2)	C3—C4—N2—O1	3.7 (2)
C6—C7—C12—C11	−177.46 (14)	C5—C4—N2—O1	−178.11 (12)
C10—C11—C12—C7	−0.1 (3)	O2—C20—O1—N2	13.6 (3)
N1—C2—C13—C14	62.89 (18)	O3—C20—O1—N2	−169.00 (13)
C3—C2—C13—C14	−61.21 (19)	C4—N2—O1—C20	−174.36 (14)
N1—C2—C13—C18	−116.10 (16)	O2—C20—O3—C21	−1.9 (3)
C3—C2—C13—C18	119.80 (17)	O1—C20—O3—C21	−179.34 (15)
C18—C13—C14—C15	1.5 (3)	C22—C21—O3—C20	160.61 (16)
C2—C13—C14—C15	−177.54 (15)	C26—C21—O3—C20	−23.1 (3)
C13—C14—C15—C16	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1	0.97	2.27	2.6881 (18)	105
C26—H26···O2	0.93	2.30	2.823 (2)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1	0.97	2.27	2.6881 (18)	105
C26—H26⋯O2	0.93	2.30	2.823 (2)	115