2,6-Bis(4-chloro-phen-yl)-1,3-dimethyl-piperidin-4-one O-benzyl-oxime.

The piperidin-4-one ring in the title compound, C(26)H(26)Cl(2)N(2)O, exists in a chair conformation with equatorial orientations of the methyl and 4-chlorophenyl groups. The C atom bonded to the oxime group is statistically planar (bond-angle sum = 360.0°) although the C-C=N bond angles are very different [117.83 (15) and 127.59 (15)°]. The dihedral angle between the chloro-phenyl rings is 54.75 (4)°. In the crystal, mol-ecules inter-act via van der Waals forces.

Related literature

For the synthesis and biological activity of piperidin-4-one derivatives, see: Parthiban et al. (2008 ▶). For related structures see: Parthiban et al. (2009a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H26Cl2N2O

M = 453.39

Monoclinic,

a = 7.6461 (2) Å

b = 18.5051 (5) Å

c = 16.7172 (5) Å

β = 91.130 (1)°

V = 2364.89 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.23 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.935, T max = 0.957

32534 measured reflections

7702 independent reflections

4010 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.02

7702 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002152/hb6599sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002152/hb6599Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002152/hb6599Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H26Cl2N2O	F(000) = 952
Mr = 453.39	Dx = 1.273 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6502 reflections
a = 7.6461 (2) Å	θ = 2.4–25.0°
b = 18.5051 (5) Å	µ = 0.30 mm−1
c = 16.7172 (5) Å	T = 298 K
β = 91.130 (1)°	Block, colourless
V = 2364.89 (11) Å3	0.23 × 0.19 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	7702 independent reflections
Radiation source: fine-focus sealed tube	4010 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 31.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→11
Tmin = 0.935, Tmax = 0.957	k = −27→27
32534 measured reflections	l = −24→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.3655P] where P = (Fo2 + 2Fc2)/3
7702 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 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
C1	0.42343 (19)	0.32793 (8)	0.56014 (10)	0.0414 (4)
H1	0.4723	0.3293	0.5064	0.050*
C2	0.2500 (2)	0.37081 (9)	0.55816 (11)	0.0445 (4)
H2	0.2058	0.3719	0.6128	0.053*
C3	0.1169 (2)	0.33229 (9)	0.50667 (11)	0.0448 (4)
C4	0.0966 (2)	0.25380 (10)	0.52509 (13)	0.0545 (5)
H4A	0.0192	0.2315	0.4856	0.065*
H4B	0.0450	0.2481	0.5773	0.065*
C5	0.2753 (2)	0.21664 (9)	0.52438 (11)	0.0466 (4)
H5	0.3232	0.2220	0.4708	0.056*
C6	0.55190 (19)	0.36477 (8)	0.61703 (10)	0.0402 (4)
C7	0.7020 (2)	0.39609 (10)	0.58833 (11)	0.0500 (4)
H7	0.7268	0.3920	0.5343	0.060*
C8	0.8164 (2)	0.43352 (10)	0.63860 (12)	0.0537 (5)
H8	0.9169	0.4545	0.6184	0.064*
C9	0.7802 (2)	0.43934 (9)	0.71775 (11)	0.0477 (4)
C10	0.6325 (2)	0.40840 (10)	0.74877 (11)	0.0524 (4)
H10	0.6090	0.4123	0.8030	0.063*
C11	0.5195 (2)	0.37142 (10)	0.69761 (11)	0.0498 (4)
H11	0.4193	0.3505	0.7181	0.060*
C12	0.2795 (2)	0.44860 (9)	0.53218 (13)	0.0585 (5)
H12A	0.3313	0.4491	0.4803	0.088*
H12B	0.3563	0.4721	0.5701	0.088*
H12C	0.1695	0.4736	0.5297	0.088*
C13	−0.1626 (3)	0.36716 (12)	0.34792 (13)	0.0639 (5)
H13A	−0.0839	0.3650	0.3032	0.077*
H13B	−0.1769	0.4173	0.3632	0.077*
C14	−0.3364 (2)	0.33482 (9)	0.32492 (10)	0.0451 (4)
C15	−0.4831 (3)	0.37759 (12)	0.32269 (13)	0.0614 (5)
H15	−0.4736	0.4264	0.3351	0.074*
C16	−0.6439 (3)	0.34904 (18)	0.30229 (18)	0.0930 (9)
H16	−0.7421	0.3787	0.3005	0.112*
C17	−0.6596 (4)	0.2789 (2)	0.28508 (19)	0.1076 (11)
H17	−0.7687	0.2597	0.2717	0.129*
C18	−0.5152 (5)	0.23537 (15)	0.28717 (18)	0.1031 (10)
H18	−0.5264	0.1865	0.2754	0.124*
C19	−0.3534 (3)	0.26358 (12)	0.30663 (15)	0.0745 (6)
H19	−0.2554	0.2338	0.3073	0.089*
C20	0.2544 (2)	0.13702 (9)	0.54100 (11)	0.0461 (4)
C21	0.1951 (3)	0.11215 (10)	0.61296 (12)	0.0601 (5)
H21	0.1680	0.1452	0.6528	0.072*
C22	0.1750 (3)	0.03941 (10)	0.62753 (13)	0.0611 (5)
H22	0.1356	0.0234	0.6768	0.073*
C23	0.2136 (2)	−0.00899 (9)	0.56869 (12)	0.0513 (5)
C24	0.2715 (3)	0.01343 (10)	0.49649 (13)	0.0579 (5)
H24	0.2967	−0.0200	0.4568	0.069*
C25	0.2924 (2)	0.08673 (10)	0.48284 (12)	0.0538 (4)
H25	0.3328	0.1023	0.4337	0.065*
C26	0.5667 (2)	0.21413 (11)	0.58121 (14)	0.0665 (6)
H26A	0.5517	0.1649	0.5980	0.100*
H26B	0.6474	0.2380	0.6171	0.100*
H26C	0.6116	0.2150	0.5280	0.100*
N1	0.39675 (17)	0.25164 (7)	0.58210 (9)	0.0436 (3)
N2	0.03573 (17)	0.36870 (8)	0.45354 (9)	0.0483 (4)
O1	−0.09336 (16)	0.32633 (7)	0.41361 (8)	0.0594 (4)
Cl1	0.92535 (7)	0.48578 (3)	0.78064 (4)	0.07529 (19)
Cl2	0.19251 (8)	−0.10122 (3)	0.58698 (4)	0.0769 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0416 (8)	0.0420 (9)	0.0404 (10)	0.0022 (6)	−0.0017 (7)	0.0006 (7)
C2	0.0414 (8)	0.0415 (9)	0.0502 (11)	0.0025 (6)	−0.0042 (7)	0.0001 (7)
C3	0.0390 (8)	0.0437 (9)	0.0515 (11)	0.0023 (6)	−0.0046 (7)	0.0026 (8)
C4	0.0500 (9)	0.0464 (10)	0.0663 (13)	−0.0052 (7)	−0.0168 (8)	0.0068 (9)
C5	0.0552 (9)	0.0434 (9)	0.0409 (10)	−0.0009 (7)	−0.0062 (8)	0.0000 (7)
C6	0.0374 (7)	0.0412 (9)	0.0418 (10)	0.0023 (6)	−0.0009 (7)	0.0025 (7)
C7	0.0435 (8)	0.0630 (11)	0.0436 (11)	−0.0010 (7)	0.0040 (7)	0.0033 (8)
C8	0.0383 (8)	0.0656 (12)	0.0572 (13)	−0.0093 (7)	0.0001 (8)	0.0096 (9)
C9	0.0461 (8)	0.0442 (9)	0.0521 (12)	−0.0036 (7)	−0.0125 (8)	0.0054 (8)
C10	0.0549 (10)	0.0620 (11)	0.0401 (10)	−0.0060 (8)	−0.0024 (8)	0.0024 (8)
C11	0.0453 (9)	0.0592 (11)	0.0449 (11)	−0.0096 (7)	0.0027 (7)	0.0052 (8)
C12	0.0523 (10)	0.0420 (9)	0.0806 (15)	0.0003 (8)	−0.0111 (9)	0.0008 (9)
C13	0.0535 (10)	0.0740 (14)	0.0634 (14)	−0.0084 (9)	−0.0160 (9)	0.0198 (11)
C14	0.0466 (8)	0.0503 (10)	0.0382 (10)	−0.0013 (7)	−0.0065 (7)	0.0043 (8)
C15	0.0599 (11)	0.0626 (12)	0.0615 (14)	0.0067 (9)	−0.0031 (9)	−0.0003 (10)
C16	0.0477 (11)	0.123 (2)	0.108 (2)	0.0021 (13)	−0.0107 (12)	0.0303 (18)
C17	0.0874 (19)	0.133 (3)	0.101 (2)	−0.0501 (19)	−0.0415 (16)	0.033 (2)
C18	0.140 (3)	0.0683 (16)	0.100 (2)	−0.0419 (18)	−0.0212 (19)	−0.0091 (15)
C19	0.0850 (15)	0.0540 (12)	0.0843 (18)	0.0041 (11)	−0.0014 (13)	−0.0030 (11)
C20	0.0525 (9)	0.0421 (9)	0.0433 (11)	0.0008 (7)	−0.0084 (8)	−0.0030 (8)
C21	0.0899 (14)	0.0454 (10)	0.0451 (12)	0.0020 (9)	0.0042 (10)	−0.0079 (9)
C22	0.0856 (14)	0.0463 (11)	0.0517 (13)	0.0003 (9)	0.0085 (10)	0.0008 (9)
C23	0.0512 (9)	0.0381 (9)	0.0645 (13)	0.0019 (7)	−0.0047 (9)	−0.0020 (8)
C24	0.0670 (11)	0.0476 (10)	0.0590 (13)	0.0039 (8)	0.0014 (10)	−0.0141 (9)
C25	0.0634 (11)	0.0513 (11)	0.0466 (11)	0.0017 (8)	0.0005 (9)	−0.0015 (9)
C26	0.0542 (10)	0.0541 (11)	0.0904 (17)	0.0145 (8)	−0.0181 (10)	−0.0080 (11)
N1	0.0446 (7)	0.0390 (7)	0.0470 (9)	0.0029 (5)	−0.0086 (6)	−0.0018 (6)
N2	0.0398 (7)	0.0491 (8)	0.0557 (10)	−0.0008 (6)	−0.0079 (6)	0.0019 (7)
O1	0.0562 (7)	0.0554 (8)	0.0658 (9)	−0.0072 (6)	−0.0249 (6)	0.0111 (6)
Cl1	0.0766 (3)	0.0786 (4)	0.0696 (4)	−0.0275 (3)	−0.0249 (3)	0.0053 (3)
Cl2	0.0885 (4)	0.0405 (3)	0.1022 (5)	−0.0008 (2)	0.0140 (3)	−0.0008 (3)

C1—N1	1.474 (2)	C13—C14	1.500 (2)
C1—C6	1.516 (2)	C13—H13A	0.9700
C1—C2	1.545 (2)	C13—H13B	0.9700
C1—H1	0.9800	C14—C19	1.359 (3)
C2—C3	1.500 (2)	C14—C15	1.373 (3)
C2—C12	1.522 (2)	C15—C16	1.375 (3)
C2—H2	0.9800	C15—H15	0.9300
C3—N2	1.268 (2)	C16—C17	1.334 (4)
C3—C4	1.493 (2)	C16—H16	0.9300
C4—C5	1.529 (2)	C17—C18	1.367 (4)
C4—H4A	0.9700	C17—H17	0.9300
C4—H4B	0.9700	C18—C19	1.376 (4)
C5—N1	1.476 (2)	C18—H18	0.9300
C5—C20	1.508 (2)	C19—H19	0.9300
C5—H5	0.9800	C20—C21	1.373 (3)
C6—C7	1.380 (2)	C20—C25	1.381 (2)
C6—C11	1.380 (3)	C21—C22	1.377 (3)
C7—C8	1.387 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.367 (3)
C8—C9	1.361 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.359 (3)
C9—C10	1.377 (2)	C23—Cl2	1.7420 (18)
C9—Cl1	1.7405 (17)	C24—C25	1.385 (3)
C10—C11	1.384 (2)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—H11	0.9300	C26—N1	1.473 (2)
C12—H12A	0.9600	C26—H26A	0.9600
C12—H12B	0.9600	C26—H26B	0.9600
C12—H12C	0.9600	C26—H26C	0.9600
C13—O1	1.426 (2)	N2—O1	1.4172 (17)
N1—C1—C6	111.45 (13)	O1—C13—H13A	110.2
N1—C1—C2	111.98 (13)	C14—C13—H13A	110.2
C6—C1—C2	109.13 (13)	O1—C13—H13B	110.2
N1—C1—H1	108.0	C14—C13—H13B	110.2
C6—C1—H1	108.0	H13A—C13—H13B	108.5
C2—C1—H1	108.0	C19—C14—C15	118.59 (18)
C3—C2—C12	112.86 (14)	C19—C14—C13	121.68 (18)
C3—C2—C1	109.90 (13)	C15—C14—C13	119.73 (17)
C12—C2—C1	111.10 (14)	C14—C15—C16	120.8 (2)
C3—C2—H2	107.6	C14—C15—H15	119.6
C12—C2—H2	107.6	C16—C15—H15	119.6
C1—C2—H2	107.6	C17—C16—C15	120.2 (2)
N2—C3—C4	127.59 (15)	C17—C16—H16	119.9
N2—C3—C2	117.83 (15)	C15—C16—H16	119.9
C4—C3—C2	114.58 (14)	C16—C17—C18	120.0 (2)
C3—C4—C5	109.83 (14)	C16—C17—H17	120.0
C3—C4—H4A	109.7	C18—C17—H17	120.0
C5—C4—H4A	109.7	C17—C18—C19	120.3 (2)
C3—C4—H4B	109.7	C17—C18—H18	119.9
C5—C4—H4B	109.7	C19—C18—H18	119.9
H4A—C4—H4B	108.2	C14—C19—C18	120.2 (2)
N1—C5—C20	112.08 (13)	C14—C19—H19	119.9
N1—C5—C4	110.38 (14)	C18—C19—H19	119.9
C20—C5—C4	109.87 (14)	C21—C20—C25	117.94 (16)
N1—C5—H5	108.1	C21—C20—C5	121.79 (16)
C20—C5—H5	108.1	C25—C20—C5	120.27 (17)
C4—C5—H5	108.1	C20—C21—C22	121.51 (18)
C7—C6—C11	117.92 (16)	C20—C21—H21	119.2
C7—C6—C1	120.25 (16)	C22—C21—H21	119.2
C11—C6—C1	121.74 (14)	C23—C22—C21	119.12 (19)
C6—C7—C8	121.20 (17)	C23—C22—H22	120.4
C6—C7—H7	119.4	C21—C22—H22	120.4
C8—C7—H7	119.4	C24—C23—C22	121.20 (17)
C9—C8—C7	119.39 (16)	C24—C23—Cl2	119.21 (15)
C9—C8—H8	120.3	C22—C23—Cl2	119.58 (16)
C7—C8—H8	120.3	C23—C24—C25	119.08 (18)
C8—C9—C10	121.14 (16)	C23—C24—H24	120.5
C8—C9—Cl1	119.13 (13)	C25—C24—H24	120.5
C10—C9—Cl1	119.72 (15)	C20—C25—C24	121.15 (19)
C9—C10—C11	118.64 (17)	C20—C25—H25	119.4
C9—C10—H10	120.7	C24—C25—H25	119.4
C11—C10—H10	120.7	N1—C26—H26A	109.5
C6—C11—C10	121.70 (16)	N1—C26—H26B	109.5
C6—C11—H11	119.2	H26A—C26—H26B	109.5
C10—C11—H11	119.2	N1—C26—H26C	109.5
C2—C12—H12A	109.5	H26A—C26—H26C	109.5
C2—C12—H12B	109.5	H26B—C26—H26C	109.5
H12A—C12—H12B	109.5	C26—N1—C1	108.81 (13)
C2—C12—H12C	109.5	C26—N1—C5	109.30 (13)
H12A—C12—H12C	109.5	C1—N1—C5	110.24 (12)
H12B—C12—H12C	109.5	C3—N2—O1	111.28 (13)
O1—C13—C14	107.43 (15)	N2—O1—C13	108.31 (13)
N1—C1—C2—C3	−52.12 (19)	C15—C16—C17—C18	−0.5 (5)
C6—C1—C2—C3	−176.00 (14)	C16—C17—C18—C19	−0.3 (5)
N1—C1—C2—C12	−177.75 (15)	C15—C14—C19—C18	−0.6 (3)
C6—C1—C2—C12	58.36 (19)	C13—C14—C19—C18	178.8 (2)
C12—C2—C3—N2	−5.6 (2)	C17—C18—C19—C14	0.8 (4)
C1—C2—C3—N2	−130.26 (16)	N1—C5—C20—C21	58.7 (2)
C12—C2—C3—C4	174.34 (16)	C4—C5—C20—C21	−64.4 (2)
C1—C2—C3—C4	49.7 (2)	N1—C5—C20—C25	−122.32 (17)
N2—C3—C4—C5	127.31 (19)	C4—C5—C20—C25	114.57 (19)
C2—C3—C4—C5	−52.7 (2)	C25—C20—C21—C22	0.4 (3)
C3—C4—C5—N1	57.3 (2)	C5—C20—C21—C22	179.46 (18)
C3—C4—C5—C20	−178.63 (15)	C20—C21—C22—C23	−0.5 (3)
N1—C1—C6—C7	121.89 (17)	C21—C22—C23—C24	0.1 (3)
C2—C1—C6—C7	−113.91 (17)	C21—C22—C23—Cl2	178.84 (16)
N1—C1—C6—C11	−61.4 (2)	C22—C23—C24—C25	0.4 (3)
C2—C1—C6—C11	62.8 (2)	Cl2—C23—C24—C25	−178.37 (15)
C11—C6—C7—C8	−0.4 (3)	C21—C20—C25—C24	0.0 (3)
C1—C6—C7—C8	176.39 (16)	C5—C20—C25—C24	−178.99 (16)
C6—C7—C8—C9	0.1 (3)	C23—C24—C25—C20	−0.5 (3)
C7—C8—C9—C10	0.3 (3)	C6—C1—N1—C26	−58.49 (18)
C7—C8—C9—Cl1	179.50 (14)	C2—C1—N1—C26	178.93 (15)
C8—C9—C10—C11	−0.5 (3)	C6—C1—N1—C5	−178.34 (13)
Cl1—C9—C10—C11	−179.66 (14)	C2—C1—N1—C5	59.08 (18)
C7—C6—C11—C10	0.2 (3)	C20—C5—N1—C26	56.2 (2)
C1—C6—C11—C10	−176.52 (16)	C4—C5—N1—C26	179.07 (15)
C9—C10—C11—C6	0.2 (3)	C20—C5—N1—C1	175.80 (14)
O1—C13—C14—C19	−55.0 (3)	C4—C5—N1—C1	−61.38 (18)
O1—C13—C14—C15	124.4 (2)	C4—C3—N2—O1	4.0 (3)
C19—C14—C15—C16	−0.1 (3)	C2—C3—N2—O1	−176.00 (14)
C13—C14—C15—C16	−179.6 (2)	C3—N2—O1—C13	−172.17 (17)
C14—C15—C16—C17	0.6 (4)	C14—C13—O1—N2	−160.21 (15)