(3E,5E)-3,5-Bis(2-chloro-benzyl-idene)-1-propyl-piperidin-4-one.

The title compound, C22H21Cl2NO, is a derivative of mono-carbonyl analogues of curcumin (MACs). The mol-ecule has an E conformation for each of the olefinic bonds. The 1-propyl-piperidin-4-one ring has a distorted chair conformation with the ring N and the C and O atoms of the carbonyl group deviating from the mean plane of the remaining four ring C atoms by 0.682 (2), -0.134 (3) and -0.340 (4) Å, respectively. The dihedral angle between the benzene rings is 26.5 (1)°. In the crystal, mol-ecules are connected by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For related structures, see: Agrawal & Mishra (2010 ▶); Liang et al. (2008 ▶, 2009 ▶); Wu et al. (2010 ▶, 2011 ▶); Zhao et al. (2010 ▶, 2012 ▶). For background to and applications of chalcones, see: Agrawal & Mishra (2010 ▶); Wu et al. (2010 ▶, 2011 ▶); Zhao et al. (2012 ▶).

Experimental

Crystal data

C22H21Cl2NO

M = 386.30

Orthorhombic,

a = 18.0123 (15) Å

b = 7.0128 (6) Å

c = 15.4364 (13) Å

V = 1949.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.29 × 0.21 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.759, T max = 1.000

11133 measured reflections

3807 independent reflections

3508 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.04

3807 reflections

236 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1812 Friedel pairs

Flack parameter: 0.01 (5)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049252/zq2188sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049252/zq2188Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049252/zq2188Isup3.cml

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

C22H21Cl2NO	F(000) = 808
Mr = 386.30	Dx = 1.316 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4766 reflections
a = 18.0123 (15) Å	θ = 5.2–54.3°
b = 7.0128 (6) Å	µ = 0.34 mm−1
c = 15.4364 (13) Å	T = 293 K
V = 1949.9 (3) Å3	Prismatic, green
Z = 4	0.29 × 0.21 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	3807 independent reflections
Radiation source: fine-focus sealed tube	3508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→22
Tmin = 0.759, Tmax = 1.000	k = −6→8
11133 measured reflections	l = −19→19

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0691P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3807 reflections	Δρmax = 0.22 e Å−3
236 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 1812 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

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
Cl1	0.78182 (4)	−0.45470 (9)	0.63636 (5)	0.0796 (2)
Cl2	0.37574 (3)	−0.55096 (7)	0.88228 (4)	0.06296 (16)
N1	0.56671 (8)	0.1169 (2)	0.77359 (10)	0.0401 (3)
O1	0.63228 (8)	−0.3652 (2)	0.89850 (10)	0.0607 (4)
C1	0.61494 (10)	−0.2139 (3)	0.86622 (12)	0.0429 (4)
C2	0.53972 (9)	−0.1287 (2)	0.88170 (12)	0.0403 (4)
C3	0.52682 (10)	0.0724 (3)	0.85301 (11)	0.0437 (4)
H3A	0.4741	0.0920	0.8438	0.052*
H3B	0.5427	0.1588	0.8984	0.052*
C4	0.64621 (10)	0.0972 (3)	0.78692 (14)	0.0474 (4)
H4A	0.6619	0.1817	0.8332	0.057*
H4B	0.6722	0.1343	0.7345	0.057*
C5	0.66643 (9)	−0.1048 (3)	0.80985 (12)	0.0423 (4)
C6	0.72557 (10)	−0.1989 (3)	0.78005 (13)	0.0449 (4)
H6	0.7282	−0.3274	0.7945	0.054*
C7	0.78713 (10)	−0.1247 (3)	0.72710 (11)	0.0426 (4)
C8	0.81962 (12)	0.0505 (3)	0.74401 (14)	0.0541 (5)
H8	0.7998	0.1274	0.7873	0.065*
C9	0.88044 (12)	0.1138 (4)	0.69847 (16)	0.0621 (6)
H9	0.9013	0.2317	0.7114	0.075*
C10	0.91043 (12)	0.0031 (4)	0.63378 (17)	0.0639 (6)
H10	0.9516	0.0458	0.6031	0.077*
C11	0.87924 (12)	−0.1711 (4)	0.61467 (15)	0.0585 (5)
H11	0.8987	−0.2461	0.5705	0.070*
C12	0.81917 (11)	−0.2330 (3)	0.66148 (12)	0.0477 (4)
C13	0.48853 (10)	−0.2435 (3)	0.91708 (11)	0.0416 (4)
H13	0.5036	−0.3681	0.9278	0.050*
C14	0.41197 (10)	−0.1981 (3)	0.94103 (11)	0.0407 (4)
C15	0.39186 (13)	−0.0247 (3)	0.97859 (13)	0.0533 (5)
H15	0.4275	0.0699	0.9857	0.064*
C16	0.31982 (14)	0.0090 (4)	1.00541 (16)	0.0658 (6)
H16	0.3074	0.1254	1.0303	0.079*
C17	0.26585 (13)	−0.1308 (4)	0.99520 (16)	0.0650 (6)
H17	0.2174	−0.1081	1.0134	0.078*
C18	0.28397 (11)	−0.3015 (3)	0.95846 (14)	0.0548 (5)
H18	0.2481	−0.3956	0.9516	0.066*
C19	0.35581 (10)	−0.3336 (3)	0.93162 (12)	0.0443 (4)
C20	0.54687 (11)	0.3110 (3)	0.74676 (12)	0.0460 (4)
H20A	0.5660	0.4001	0.7893	0.055*
H20B	0.4932	0.3224	0.7465	0.055*
C21	0.57591 (14)	0.3668 (3)	0.65862 (15)	0.0645 (6)
H21A	0.6297	0.3709	0.6603	0.077*
H21B	0.5614	0.2709	0.6166	0.077*
C22	0.54679 (16)	0.5583 (3)	0.63016 (19)	0.0746 (7)
H22A	0.4937	0.5525	0.6249	0.112*
H22B	0.5681	0.5912	0.5751	0.112*
H22C	0.5600	0.6531	0.6723	0.112*

	U11	U22	U33	U12	U13	U23
Cl1	0.0878 (4)	0.0597 (4)	0.0914 (4)	−0.0037 (3)	0.0140 (4)	−0.0267 (3)
Cl2	0.0552 (3)	0.0512 (3)	0.0825 (4)	−0.0052 (2)	0.0007 (3)	−0.0101 (3)
N1	0.0345 (7)	0.0385 (7)	0.0474 (7)	−0.0002 (6)	0.0026 (6)	−0.0018 (6)
O1	0.0486 (8)	0.0557 (8)	0.0777 (10)	0.0103 (6)	0.0083 (7)	0.0159 (8)
C1	0.0367 (9)	0.0427 (9)	0.0494 (10)	0.0020 (7)	−0.0036 (7)	−0.0021 (8)
C2	0.0364 (8)	0.0445 (9)	0.0399 (8)	0.0012 (7)	0.0007 (7)	−0.0042 (8)
C3	0.0384 (9)	0.0438 (9)	0.0489 (10)	0.0014 (7)	0.0073 (7)	−0.0042 (7)
C4	0.0351 (9)	0.0475 (10)	0.0596 (11)	−0.0032 (8)	0.0020 (8)	−0.0013 (9)
C5	0.0311 (9)	0.0487 (10)	0.0472 (9)	−0.0006 (7)	−0.0034 (7)	−0.0050 (8)
C6	0.0365 (9)	0.0485 (10)	0.0496 (9)	0.0005 (7)	−0.0017 (8)	−0.0029 (8)
C7	0.0339 (9)	0.0489 (10)	0.0451 (9)	0.0068 (7)	−0.0036 (7)	−0.0020 (8)
C8	0.0389 (11)	0.0635 (13)	0.0600 (12)	−0.0005 (9)	−0.0006 (9)	−0.0133 (10)
C9	0.0427 (11)	0.0660 (13)	0.0776 (15)	−0.0089 (10)	0.0006 (10)	0.0011 (12)
C10	0.0419 (11)	0.0811 (15)	0.0688 (13)	−0.0005 (10)	0.0107 (10)	0.0121 (12)
C11	0.0520 (12)	0.0744 (15)	0.0490 (10)	0.0166 (10)	0.0083 (9)	−0.0003 (10)
C12	0.0417 (10)	0.0518 (11)	0.0495 (10)	0.0078 (8)	−0.0044 (8)	−0.0035 (8)
C13	0.0389 (9)	0.0433 (9)	0.0425 (9)	0.0027 (7)	0.0016 (7)	−0.0009 (7)
C14	0.0400 (9)	0.0430 (9)	0.0391 (8)	0.0054 (7)	0.0028 (7)	0.0062 (7)
C15	0.0591 (12)	0.0473 (11)	0.0535 (11)	0.0017 (9)	0.0146 (10)	0.0030 (9)
C16	0.0690 (15)	0.0582 (12)	0.0703 (14)	0.0132 (11)	0.0272 (12)	0.0026 (11)
C17	0.0487 (12)	0.0756 (15)	0.0708 (14)	0.0113 (11)	0.0225 (11)	0.0160 (12)
C18	0.0394 (10)	0.0651 (13)	0.0598 (11)	−0.0013 (9)	0.0070 (8)	0.0163 (10)
C19	0.0431 (9)	0.0449 (10)	0.0450 (9)	0.0029 (8)	0.0027 (8)	0.0097 (8)
C20	0.0436 (10)	0.0434 (10)	0.0508 (10)	0.0028 (8)	0.0052 (8)	−0.0024 (8)
C21	0.0701 (15)	0.0563 (13)	0.0671 (13)	0.0111 (10)	0.0247 (12)	0.0092 (10)
C22	0.0879 (18)	0.0614 (14)	0.0746 (15)	0.0123 (11)	0.0157 (14)	0.0184 (12)

Cl1—C12	1.738 (2)	C10—H10	0.9300
Cl2—C19	1.741 (2)	C11—C12	1.372 (3)
N1—C4	1.453 (2)	C11—H11	0.9300
N1—C3	1.455 (2)	C13—C14	1.463 (2)
N1—C20	1.466 (2)	C13—H13	0.9300
O1—C1	1.213 (2)	C14—C15	1.395 (3)
C1—C5	1.484 (3)	C14—C19	1.396 (3)
C1—C2	1.500 (2)	C15—C16	1.382 (3)
C2—C13	1.340 (2)	C15—H15	0.9300
C2—C3	1.497 (3)	C16—C17	1.390 (4)
C3—H3A	0.9700	C16—H16	0.9300
C3—H3B	0.9700	C17—C18	1.364 (3)
C4—C5	1.505 (3)	C17—H17	0.9300
C4—H4A	0.9700	C18—C19	1.377 (3)
C4—H4B	0.9700	C18—H18	0.9300
C5—C6	1.335 (3)	C20—C21	1.509 (3)
C6—C7	1.472 (3)	C20—H20A	0.9700
C6—H6	0.9300	C20—H20B	0.9700
C7—C8	1.386 (3)	C21—C22	1.507 (3)
C7—C12	1.391 (3)	C21—H21A	0.9700
C8—C9	1.375 (3)	C21—H21B	0.9700
C8—H8	0.9300	C22—H22A	0.9600
C9—C10	1.376 (4)	C22—H22B	0.9600
C9—H9	0.9300	C22—H22C	0.9600
C10—C11	1.377 (3)
C4—N1—C3	110.30 (15)	C11—C12—C7	122.6 (2)
C4—N1—C20	111.63 (14)	C11—C12—Cl1	118.09 (16)
C3—N1—C20	108.46 (14)	C7—C12—Cl1	119.35 (16)
O1—C1—C5	122.06 (16)	C2—C13—C14	128.35 (17)
O1—C1—C2	121.03 (17)	C2—C13—H13	115.8
C5—C1—C2	116.91 (15)	C14—C13—H13	115.8
C13—C2—C3	125.45 (16)	C15—C14—C19	116.66 (17)
C13—C2—C1	116.55 (15)	C15—C14—C13	122.67 (18)
C3—C2—C1	117.94 (15)	C19—C14—C13	120.57 (17)
N1—C3—C2	112.02 (14)	C16—C15—C14	121.1 (2)
N1—C3—H3A	109.2	C16—C15—H15	119.4
C2—C3—H3A	109.2	C14—C15—H15	119.4
N1—C3—H3B	109.2	C15—C16—C17	120.2 (2)
C2—C3—H3B	109.2	C15—C16—H16	119.9
H3A—C3—H3B	107.9	C17—C16—H16	119.9
N1—C4—C5	111.19 (15)	C18—C17—C16	119.9 (2)
N1—C4—H4A	109.4	C18—C17—H17	120.0
C5—C4—H4A	109.4	C16—C17—H17	120.0
N1—C4—H4B	109.4	C17—C18—C19	119.6 (2)
C5—C4—H4B	109.4	C17—C18—H18	120.2
H4A—C4—H4B	108.0	C19—C18—H18	120.2
C6—C5—C1	116.51 (18)	C18—C19—C14	122.58 (18)
C6—C5—C4	125.24 (17)	C18—C19—Cl2	117.92 (16)
C1—C5—C4	118.16 (15)	C14—C19—Cl2	119.49 (14)
C5—C6—C7	128.18 (18)	N1—C20—C21	114.26 (16)
C5—C6—H6	115.9	N1—C20—H20A	108.7
C7—C6—H6	115.9	C21—C20—H20A	108.7
C8—C7—C12	116.48 (18)	N1—C20—H20B	108.7
C8—C7—C6	121.77 (17)	C21—C20—H20B	108.7
C12—C7—C6	121.59 (18)	H20A—C20—H20B	107.6
C9—C8—C7	121.8 (2)	C22—C21—C20	111.92 (18)
C9—C8—H8	119.1	C22—C21—H21A	109.2
C7—C8—H8	119.1	C20—C21—H21A	109.2
C8—C9—C10	120.1 (2)	C22—C21—H21B	109.2
C8—C9—H9	119.9	C20—C21—H21B	109.2
C10—C9—H9	119.9	H21A—C21—H21B	107.9
C9—C10—C11	119.8 (2)	C21—C22—H22A	109.5
C9—C10—H10	120.1	C21—C22—H22B	109.5
C11—C10—H10	120.1	H22A—C22—H22B	109.5
C12—C11—C10	119.3 (2)	C21—C22—H22C	109.5
C12—C11—H11	120.3	H22A—C22—H22C	109.5
C10—C11—H11	120.3	H22B—C22—H22C	109.5
O1—C1—C2—C13	−13.3 (3)	C10—C11—C12—C7	1.3 (3)
C5—C1—C2—C13	166.64 (16)	C10—C11—C12—Cl1	−179.34 (18)
O1—C1—C2—C3	169.50 (17)	C8—C7—C12—C11	−0.7 (3)
C5—C1—C2—C3	−10.6 (2)	C6—C7—C12—C11	−176.22 (19)
C4—N1—C3—C2	−61.51 (19)	C8—C7—C12—Cl1	179.91 (15)
C20—N1—C3—C2	175.95 (15)	C6—C7—C12—Cl1	4.4 (2)
C13—C2—C3—N1	−141.92 (17)	C3—C2—C13—C14	−4.6 (3)
C1—C2—C3—N1	35.0 (2)	C1—C2—C13—C14	178.42 (17)
C3—N1—C4—C5	62.3 (2)	C2—C13—C14—C15	−39.3 (3)
C20—N1—C4—C5	−177.01 (15)	C2—C13—C14—C19	144.50 (18)
O1—C1—C5—C6	14.9 (3)	C19—C14—C15—C16	0.4 (3)
C2—C1—C5—C6	−164.98 (16)	C13—C14—C15—C16	−175.87 (19)
O1—C1—C5—C4	−168.33 (18)	C14—C15—C16—C17	0.0 (3)
C2—C1—C5—C4	11.8 (2)	C15—C16—C17—C18	−0.1 (4)
N1—C4—C5—C6	139.18 (19)	C16—C17—C18—C19	−0.1 (3)
N1—C4—C5—C1	−37.3 (2)	C17—C18—C19—C14	0.5 (3)
C1—C5—C6—C7	−176.63 (18)	C17—C18—C19—Cl2	−178.21 (17)
C4—C5—C6—C7	6.9 (3)	C15—C14—C19—C18	−0.7 (3)
C5—C6—C7—C8	42.7 (3)	C13—C14—C19—C18	175.70 (17)
C5—C6—C7—C12	−142.0 (2)	C15—C14—C19—Cl2	178.04 (14)
C12—C7—C8—C9	−0.2 (3)	C13—C14—C19—Cl2	−5.6 (2)
C6—C7—C8—C9	175.4 (2)	C4—N1—C20—C21	66.3 (2)
C7—C8—C9—C10	0.4 (4)	C3—N1—C20—C21	−171.97 (18)
C8—C9—C10—C11	0.1 (4)	N1—C20—C21—C22	173.6 (2)
C9—C10—C11—C12	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O1i	0.97	2.64	3.607 (3)	174
C8—H8···Cg1ii	0.93	2.89	3.568	131
C21—H21B···Cg1iii	0.97	3.01	3.613	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20A⋯O1i	0.97	2.64	3.607 (3)	174
C8—H8⋯Cg1ii	0.93	2.89	3.568	131
C21—H21B⋯Cg1iii	0.97	3.01	3.613	121

Symmetry codes: (i) ; (ii) ; (iii) .