(3E,5E)-1-Allyl-3,5-bis(4-meth-oxy-benzyl-idene)-piperidin-4-one.

The piperidine ring in the title compound, C24H25NO3, adopts an envelope conformation with the N atom being the flap atom, and each C=C double bond exhibits an E conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules, forming supramolecular layers that stack along the a axis.

Related literature

For background to piperidine ring systems, see: Guengerich et al. (1973 ▶); Puder et al. (2000 ▶). For the biological importance of the title compound, see: Dimmock, Elias et al. (1999 ▶); Dimmock, Kandepu et al. (1999 ▶). For a similar structure, see: Suresh et al. (2007 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H25NO3

M = 375.45

Monoclinic,

a = 19.2409 (15) Å

b = 6.8457 (6) Å

c = 15.6393 (13) Å

β = 98.255 (2)°

V = 2038.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.34 × 0.33 × 0.21 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.984

22074 measured reflections

5935 independent reflections

3680 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.169

S = 1.03

5935 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.19 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015195/tk5227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015195/tk5227Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015195/tk5227Isup3.cml

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

C24H25NO3	F(000) = 800
Mr = 375.45	Dx = 1.223 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 19.2409 (15) Å	θ = 2–30°
b = 6.8457 (6) Å	µ = 0.08 mm−1
c = 15.6393 (13) Å	T = 293 K
β = 98.255 (2)°	Block, colourless
V = 2038.6 (3) Å3	0.34 × 0.33 × 0.21 mm
Z = 4

Bruker Kappa APEXII diffractometer	5935 independent reflections
Radiation source: fine-focus sealed tube	3680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 0 pixels mm-1	θmax = 30.0°, θmin = 2.1°
ω and φ scans	h = −27→27
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.973, Tmax = 0.984	l = −22→22
22074 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0905P)2 + 0.0856P] where P = (Fo2 + 2Fc2)/3
5935 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.19 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
O1	0.54889 (6)	0.02740 (19)	0.11269 (10)	0.0792 (4)
O2	0.20688 (7)	0.68527 (18)	0.21213 (10)	0.0775 (4)
O3	−0.14813 (6)	0.6458 (2)	0.45644 (8)	0.0682 (3)
N1	0.21732 (5)	0.20325 (16)	0.35611 (7)	0.0421 (3)
C1	0.43254 (8)	0.4039 (2)	0.16588 (11)	0.0598 (4)
H1A	0.4346	0.5385	0.1740	0.072*
C2	0.49119 (8)	0.3075 (3)	0.14716 (13)	0.0651 (5)
H2A	0.5325	0.3761	0.1444	0.078*
C3	0.48852 (8)	0.1090 (2)	0.13251 (10)	0.0550 (4)
C4	0.42736 (8)	0.0081 (2)	0.13796 (10)	0.0563 (4)
H4A	0.4252	−0.1257	0.1277	0.068*
C5	0.36911 (7)	0.1063 (2)	0.15869 (10)	0.0526 (4)
H5A	0.3283	0.0364	0.1631	0.063*
C6	0.37000 (7)	0.3065 (2)	0.17309 (9)	0.0473 (3)
C7	0.31027 (7)	0.4208 (2)	0.19275 (9)	0.0501 (3)
H7A	0.3086	0.5484	0.1722	0.060*
C8	0.25757 (7)	0.3710 (2)	0.23565 (9)	0.0445 (3)
C9	0.25089 (7)	0.1769 (2)	0.27873 (9)	0.0449 (3)
H9A	0.2230	0.0889	0.2390	0.054*
H9B	0.2970	0.1196	0.2945	0.054*
C10	0.14497 (7)	0.2688 (2)	0.33075 (9)	0.0438 (3)
H10A	0.1205	0.2705	0.3809	0.053*
H10B	0.1206	0.1791	0.2887	0.053*
C11	0.14472 (6)	0.4704 (2)	0.29240 (9)	0.0430 (3)
C12	0.20337 (7)	0.5227 (2)	0.24397 (10)	0.0493 (3)
C13	0.09767 (7)	0.6104 (2)	0.30150 (9)	0.0456 (3)
H13A	0.1067	0.7300	0.2770	0.055*
C14	0.03457 (7)	0.6064 (2)	0.34352 (8)	0.0448 (3)
C15	−0.00436 (7)	0.4391 (2)	0.35423 (9)	0.0485 (3)
H15A	0.0109	0.3196	0.3356	0.058*
C16	−0.06544 (7)	0.4458 (2)	0.39197 (9)	0.0510 (3)
H16A	−0.0906	0.3320	0.3983	0.061*
C17	−0.08852 (7)	0.6221 (2)	0.42007 (9)	0.0511 (4)
C18	−0.05055 (9)	0.7910 (2)	0.41030 (11)	0.0601 (4)
H18A	−0.0656	0.9099	0.4297	0.072*
C19	0.00918 (8)	0.7825 (2)	0.37195 (10)	0.0550 (4)
H19A	0.0335	0.8973	0.3647	0.066*
C20	0.55156 (11)	−0.1755 (3)	0.10006 (14)	0.0770 (5)
H20A	0.5972	−0.2110	0.0871	0.116*
H20B	0.5165	−0.2125	0.0529	0.116*
H20C	0.5429	−0.2415	0.1516	0.116*
C21	−0.18746 (8)	0.4758 (3)	0.47126 (12)	0.0704 (5)
H21A	−0.2279	0.5130	0.4971	0.106*
H21B	−0.1586	0.3890	0.5094	0.106*
H21C	−0.2024	0.4110	0.4173	0.106*
C22	0.21975 (7)	0.0227 (2)	0.40710 (10)	0.0496 (3)
H22A	0.2046	−0.0860	0.3692	0.060*
H22B	0.1875	0.0335	0.4491	0.060*
C23	0.29171 (9)	−0.0170 (3)	0.45282 (11)	0.0654 (4)
H23A	0.3125	0.0780	0.4907	0.079*
C24	0.32751 (11)	−0.1738 (4)	0.44379 (16)	0.0994 (8)
H24C	0.3085	−0.2720	0.4065	0.119*
H24A	0.3723	−0.1884	0.4746	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0652 (7)	0.0575 (8)	0.1236 (11)	0.0088 (6)	0.0433 (7)	0.0043 (7)
O2	0.0787 (8)	0.0532 (7)	0.1092 (10)	0.0193 (6)	0.0431 (7)	0.0334 (7)
O3	0.0634 (6)	0.0774 (9)	0.0692 (7)	0.0096 (6)	0.0277 (6)	−0.0027 (6)
N1	0.0428 (5)	0.0382 (6)	0.0462 (6)	0.0033 (5)	0.0093 (4)	0.0052 (5)
C1	0.0638 (9)	0.0407 (9)	0.0803 (11)	−0.0020 (7)	0.0286 (8)	0.0058 (7)
C2	0.0574 (9)	0.0503 (10)	0.0933 (13)	−0.0061 (7)	0.0308 (8)	0.0056 (9)
C3	0.0543 (8)	0.0500 (9)	0.0641 (9)	0.0048 (7)	0.0202 (7)	0.0044 (7)
C4	0.0624 (9)	0.0424 (8)	0.0669 (9)	−0.0012 (7)	0.0186 (7)	−0.0032 (7)
C5	0.0501 (7)	0.0487 (9)	0.0602 (9)	−0.0052 (6)	0.0125 (6)	−0.0022 (7)
C6	0.0506 (7)	0.0458 (8)	0.0473 (7)	0.0027 (6)	0.0132 (6)	0.0075 (6)
C7	0.0537 (7)	0.0438 (8)	0.0548 (8)	0.0043 (6)	0.0151 (6)	0.0097 (6)
C8	0.0468 (7)	0.0404 (8)	0.0469 (7)	0.0023 (6)	0.0085 (5)	0.0032 (6)
C9	0.0460 (6)	0.0404 (7)	0.0498 (7)	0.0026 (6)	0.0123 (5)	0.0021 (6)
C10	0.0398 (6)	0.0419 (7)	0.0503 (7)	0.0016 (5)	0.0080 (5)	0.0021 (6)
C11	0.0417 (6)	0.0404 (7)	0.0461 (7)	0.0020 (5)	0.0035 (5)	0.0012 (6)
C12	0.0511 (7)	0.0435 (8)	0.0547 (8)	0.0061 (6)	0.0122 (6)	0.0088 (7)
C13	0.0456 (6)	0.0413 (7)	0.0491 (7)	0.0031 (6)	0.0040 (5)	0.0037 (6)
C14	0.0443 (6)	0.0434 (8)	0.0454 (7)	0.0058 (6)	0.0014 (5)	0.0006 (6)
C15	0.0427 (6)	0.0442 (8)	0.0576 (8)	0.0043 (6)	0.0034 (6)	−0.0060 (6)
C16	0.0466 (7)	0.0492 (9)	0.0565 (8)	−0.0003 (6)	0.0049 (6)	−0.0011 (7)
C17	0.0488 (7)	0.0611 (10)	0.0437 (7)	0.0097 (7)	0.0078 (6)	−0.0007 (7)
C18	0.0688 (9)	0.0478 (9)	0.0662 (10)	0.0134 (8)	0.0176 (8)	−0.0034 (7)
C19	0.0610 (8)	0.0414 (8)	0.0643 (9)	0.0052 (7)	0.0145 (7)	0.0023 (7)
C20	0.0843 (12)	0.0616 (12)	0.0891 (14)	0.0203 (10)	0.0259 (10)	−0.0022 (10)
C21	0.0566 (9)	0.0971 (15)	0.0604 (9)	−0.0052 (9)	0.0180 (7)	−0.0085 (10)
C22	0.0515 (7)	0.0427 (8)	0.0566 (8)	0.0023 (6)	0.0141 (6)	0.0092 (6)
C23	0.0619 (9)	0.0723 (12)	0.0616 (9)	0.0051 (9)	0.0075 (7)	0.0234 (9)
C24	0.0765 (12)	0.1123 (19)	0.1129 (17)	0.0407 (13)	0.0262 (12)	0.0450 (15)

O1—C3	1.3639 (18)	C11—C13	1.3403 (19)
O1—C20	1.405 (2)	C11—C12	1.4902 (19)
O2—C12	1.2253 (18)	C13—C14	1.4614 (19)
O3—C17	1.3611 (17)	C13—H13A	0.9300
O3—C21	1.425 (2)	C14—C15	1.392 (2)
N1—C10	1.4623 (16)	C14—C19	1.397 (2)
N1—C9	1.4624 (17)	C15—C16	1.3896 (19)
N1—C22	1.4681 (18)	C15—H15A	0.9300
C1—C2	1.375 (2)	C16—C17	1.380 (2)
C1—C6	1.394 (2)	C16—H16A	0.9300
C1—H1A	0.9300	C17—C18	1.388 (2)
C2—C3	1.378 (2)	C18—C19	1.372 (2)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.378 (2)	C19—H19A	0.9300
C4—C5	1.385 (2)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C5—C6	1.389 (2)	C20—H20C	0.9600
C5—H5A	0.9300	C21—H21A	0.9600
C6—C7	1.4589 (19)	C21—H21B	0.9600
C7—C8	1.3379 (19)	C21—H21C	0.9600
C7—H7A	0.9300	C22—C23	1.489 (2)
C8—C12	1.4906 (19)	C22—H22A	0.9700
C8—C9	1.5033 (19)	C22—H22B	0.9700
C9—H9A	0.9700	C23—C24	1.295 (3)
C9—H9B	0.9700	C23—H23A	0.9300
C10—C11	1.5040 (19)	C24—H24C	0.9300
C10—H10A	0.9700	C24—H24A	0.9300
C10—H10B	0.9700
C3—O1—C20	119.09 (14)	C11—C12—C8	117.87 (12)
C17—O3—C21	118.02 (13)	C11—C13—C14	130.67 (13)
C10—N1—C9	109.25 (11)	C11—C13—H13A	114.7
C10—N1—C22	111.15 (10)	C14—C13—H13A	114.7
C9—N1—C22	111.25 (11)	C15—C14—C19	116.93 (13)
C2—C1—C6	122.13 (15)	C15—C14—C13	124.46 (13)
C2—C1—H1A	118.9	C19—C14—C13	118.56 (13)
C6—C1—H1A	118.9	C16—C15—C14	121.79 (14)
C1—C2—C3	119.80 (14)	C16—C15—H15A	119.1
C1—C2—H2A	120.1	C14—C15—H15A	119.1
C3—C2—H2A	120.1	C17—C16—C15	119.64 (15)
O1—C3—C4	124.88 (15)	C17—C16—H16A	120.2
O1—C3—C2	115.40 (14)	C15—C16—H16A	120.2
C4—C3—C2	119.72 (14)	O3—C17—C16	124.50 (15)
C3—C4—C5	119.90 (15)	O3—C17—C18	115.81 (14)
C3—C4—H4A	120.1	C16—C17—C18	119.68 (13)
C5—C4—H4A	120.1	C19—C18—C17	120.02 (15)
C4—C5—C6	121.71 (13)	C19—C18—H18A	120.0
C4—C5—H5A	119.1	C17—C18—H18A	120.0
C6—C5—H5A	119.1	C18—C19—C14	121.94 (15)
C5—C6—C1	116.72 (13)	C18—C19—H19A	119.0
C5—C6—C7	124.86 (13)	C14—C19—H19A	119.0
C1—C6—C7	118.41 (14)	O1—C20—H20A	109.5
C8—C7—C6	130.23 (14)	O1—C20—H20B	109.5
C8—C7—H7A	114.9	H20A—C20—H20B	109.5
C6—C7—H7A	114.9	O1—C20—H20C	109.5
C7—C8—C12	117.16 (13)	H20A—C20—H20C	109.5
C7—C8—C9	124.73 (12)	H20B—C20—H20C	109.5
C12—C8—C9	118.06 (11)	O3—C21—H21A	109.5
N1—C9—C8	109.79 (11)	O3—C21—H21B	109.5
N1—C9—H9A	109.7	H21A—C21—H21B	109.5
C8—C9—H9A	109.7	O3—C21—H21C	109.5
N1—C9—H9B	109.7	H21A—C21—H21C	109.5
C8—C9—H9B	109.7	H21B—C21—H21C	109.5
H9A—C9—H9B	108.2	N1—C22—C23	111.66 (12)
N1—C10—C11	109.77 (10)	N1—C22—H22A	109.3
N1—C10—H10A	109.7	C23—C22—H22A	109.3
C11—C10—H10A	109.7	N1—C22—H22B	109.3
N1—C10—H10B	109.7	C23—C22—H22B	109.3
C11—C10—H10B	109.7	H22A—C22—H22B	107.9
H10A—C10—H10B	108.2	C24—C23—C22	124.8 (2)
C13—C11—C12	117.03 (13)	C24—C23—H23A	117.6
C13—C11—C10	125.27 (12)	C22—C23—H23A	117.6
C12—C11—C10	117.63 (11)	C23—C24—H24C	120.0
O2—C12—C11	120.98 (13)	C23—C24—H24A	120.0
O2—C12—C8	121.15 (13)	H24C—C24—H24A	120.0
C6—C1—C2—C3	1.8 (3)	C13—C11—C12—C8	178.01 (12)
C20—O1—C3—C4	−2.8 (3)	C10—C11—C12—C8	0.94 (19)
C20—O1—C3—C2	177.57 (18)	C7—C8—C12—O2	0.6 (2)
C1—C2—C3—O1	178.69 (16)	C9—C8—C12—O2	178.19 (15)
C1—C2—C3—C4	−0.9 (3)	C7—C8—C12—C11	−179.34 (13)
O1—C3—C4—C5	179.97 (15)	C9—C8—C12—C11	−1.73 (19)
C2—C3—C4—C5	−0.5 (3)	C12—C11—C13—C14	179.02 (13)
C3—C4—C5—C6	1.0 (2)	C10—C11—C13—C14	−4.2 (2)
C4—C5—C6—C1	−0.2 (2)	C11—C13—C14—C15	−26.2 (2)
C4—C5—C6—C7	178.18 (14)	C11—C13—C14—C19	156.73 (15)
C2—C1—C6—C5	−1.3 (2)	C19—C14—C15—C16	−0.4 (2)
C2—C1—C6—C7	−179.72 (16)	C13—C14—C15—C16	−177.60 (12)
C5—C6—C7—C8	31.9 (2)	C14—C15—C16—C17	−0.2 (2)
C1—C6—C7—C8	−149.75 (16)	C21—O3—C17—C16	3.8 (2)
C6—C7—C8—C12	−179.27 (14)	C21—O3—C17—C18	−177.41 (14)
C6—C7—C8—C9	3.3 (2)	C15—C16—C17—O3	178.79 (13)
C10—N1—C9—C8	65.73 (14)	C15—C16—C17—C18	0.1 (2)
C22—N1—C9—C8	−171.19 (11)	O3—C17—C18—C19	−178.09 (14)
C7—C8—C9—N1	146.84 (14)	C16—C17—C18—C19	0.8 (2)
C12—C8—C9—N1	−30.56 (17)	C17—C18—C19—C14	−1.5 (3)
C9—N1—C10—C11	−66.65 (14)	C15—C14—C19—C18	1.3 (2)
C22—N1—C10—C11	170.21 (11)	C13—C14—C19—C18	178.60 (14)
N1—C10—C11—C13	−144.68 (13)	C10—N1—C22—C23	−164.76 (13)
N1—C10—C11—C12	32.13 (17)	C9—N1—C22—C23	73.26 (16)
C13—C11—C12—O2	−1.9 (2)	N1—C22—C23—C24	−122.02 (19)
C10—C11—C12—O2	−178.98 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3i	0.97	2.59	3.3710 (18)	138
C21—H21C···O2ii	0.96	2.54	3.466 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O3i	0.97	2.59	3.3710 (18)	138
C21—H21C⋯O2ii	0.96	2.54	3.466 (2)	163

Symmetry codes: (i) ; (ii) .