1-Acryloyl-2,6-bis-(4-chloro-phen-yl)-3,5-dimethyl-piperidin-4-one.

In the crystal structure of the title compound, C(22)H(21)Cl(2)NO(2), the piperidinone ring is in a boat conformation.

Related literature

For the bioactivity of piperidin-4-ones, see: Jerom & Spencer (1988 ▶); Bochringer & Shochne (1961 ▶); Mobio et al. (1989 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶). For the synthesis, see: Baliah et al., (1983 ▶). For a related structure, see: Ompraba et al. (2003 ▶).

Experimental

Crystal data

C22H21Cl2NO2

M = 402.30

Monoclinic,

a = 10.2410 (8) Å

b = 19.5070 (11) Å

c = 10.9760 (9) Å

β = 112.567 (2)°

V = 2024.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.30 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer

Absorption correction: none

6713 measured reflections

3542 independent reflections

2800 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.03

3542 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010472/pk2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010472/pk2157Isup2.hkl

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

C22H21Cl2NO2	F(000) = 840
Mr = 402.30	Dx = 1.320 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6713 reflections
a = 10.2410 (8) Å	θ = 3.0–25.0°
b = 19.5070 (11) Å	µ = 0.34 mm−1
c = 10.9760 (9) Å	T = 293 K
β = 112.567 (2)°	Block, colourless
V = 2024.8 (3) Å3	0.30 × 0.27 × 0.25 mm
Z = 4

MacScience DIPLabo 32001 diffractometer	2800 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 25.0°, θmin = 3.0°
Detector resolution: 10.0 pixels mm-1	h = −12→12
ω scans	k = −23→23
6713 measured reflections	l = −13→13
3542 independent reflections

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.7531P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3542 reflections	Δρmax = 0.20 e Å−3
247 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (15)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl16	0.26934 (10)	0.75475 (4)	0.51117 (9)	0.1061 (4)
Cl27	0.37661 (8)	0.35272 (4)	0.88810 (6)	0.0863 (3)
O8	0.44186 (17)	0.35510 (9)	0.20478 (18)	0.0739 (7)
O18	−0.06985 (15)	0.51370 (8)	0.12166 (15)	0.0631 (6)
N1	0.09295 (16)	0.43755 (8)	0.24406 (16)	0.0460 (5)
C2	0.1348 (2)	0.36689 (10)	0.2923 (2)	0.0487 (6)
C3	0.2196 (2)	0.33554 (11)	0.2177 (2)	0.0524 (7)
C4	0.3467 (2)	0.37817 (11)	0.2317 (2)	0.0507 (7)
C5	0.3488 (2)	0.45090 (10)	0.2808 (2)	0.0475 (6)
C6	0.20081 (19)	0.48388 (10)	0.23015 (19)	0.0449 (6)
C7	0.1287 (2)	0.32667 (14)	0.0708 (2)	0.0694 (8)
C9	0.4536 (2)	0.49632 (13)	0.2509 (3)	0.0714 (9)
C10	0.2080 (2)	0.55179 (10)	0.29977 (19)	0.0466 (6)
C11	0.2401 (2)	0.55513 (11)	0.4340 (2)	0.0571 (7)
C12	0.2581 (2)	0.61714 (12)	0.4992 (2)	0.0627 (8)
C13	0.2426 (2)	0.67645 (11)	0.4290 (3)	0.0631 (8)
C14	0.2087 (3)	0.67519 (12)	0.2960 (3)	0.0735 (10)
C15	0.1915 (3)	0.61283 (12)	0.2318 (2)	0.0636 (8)
C17	−0.0434 (2)	0.45859 (11)	0.1803 (2)	0.0512 (7)
C19	−0.1601 (2)	0.41532 (13)	0.1856 (3)	0.0693 (9)
C20	−0.2902 (3)	0.43327 (19)	0.1270 (3)	0.0892 (13)
C21	0.2020 (2)	0.36349 (10)	0.4431 (2)	0.0490 (6)
C22	0.3290 (2)	0.33092 (11)	0.5125 (2)	0.0569 (8)
C23	0.3825 (2)	0.32739 (12)	0.6491 (2)	0.0628 (8)
C24	0.3089 (3)	0.35647 (11)	0.7166 (2)	0.0594 (8)
C25	0.1816 (3)	0.38854 (13)	0.6510 (2)	0.0658 (9)
C26	0.1296 (2)	0.39179 (12)	0.5151 (2)	0.0600 (8)
H2	0.04690	0.34050	0.26590	0.0580*
H3	0.25260	0.29010	0.25510	0.0630*
H5	0.38110	0.44830	0.37710	0.0570*
H6	0.17350	0.49350	0.13600	0.0540*
H7A	0.09920	0.37090	0.03120	0.1040*
H7B	0.04700	0.29960	0.06080	0.1040*
H7C	0.18290	0.30400	0.02820	0.1040*
H9A	0.54450	0.47450	0.28190	0.1070*
H9B	0.46110	0.53970	0.29450	0.1070*
H9C	0.42130	0.50350	0.15740	0.1070*
H11	0.24990	0.51470	0.48150	0.0690*
H12	0.28050	0.61850	0.58970	0.0750*
H14	0.19730	0.71590	0.24900	0.0880*
H15	0.16830	0.61200	0.14120	0.0760*
H19	−0.13880	0.37430	0.23230	0.0830*
H20A	−0.31280	0.47420	0.08010	0.1070*
H20B	−0.36180	0.40530	0.13170	0.1070*
H22	0.37920	0.31110	0.46670	0.0680*
H23	0.46800	0.30540	0.69450	0.0750*
H25	0.13140	0.40770	0.69740	0.0790*
H26	0.04360	0.41360	0.47040	0.0720*

	U11	U22	U33	U12	U13	U23
Cl16	0.1353 (7)	0.0604 (4)	0.1182 (7)	0.0015 (4)	0.0437 (6)	−0.0258 (4)
Cl27	0.1033 (6)	0.0961 (5)	0.0559 (4)	−0.0045 (4)	0.0265 (4)	0.0072 (3)
O8	0.0597 (10)	0.0782 (11)	0.0950 (13)	0.0049 (8)	0.0422 (9)	−0.0148 (9)
O18	0.0510 (9)	0.0705 (10)	0.0633 (10)	0.0131 (7)	0.0168 (7)	0.0124 (8)
N1	0.0388 (9)	0.0478 (9)	0.0506 (9)	0.0018 (7)	0.0162 (7)	0.0009 (7)
C2	0.0431 (11)	0.0457 (10)	0.0580 (12)	−0.0012 (8)	0.0202 (9)	−0.0002 (9)
C3	0.0541 (12)	0.0481 (11)	0.0566 (12)	0.0027 (9)	0.0229 (10)	−0.0034 (9)
C4	0.0445 (11)	0.0594 (12)	0.0490 (11)	0.0057 (9)	0.0187 (9)	0.0014 (9)
C5	0.0430 (11)	0.0511 (11)	0.0494 (11)	−0.0004 (8)	0.0187 (9)	0.0013 (9)
C6	0.0415 (10)	0.0483 (11)	0.0441 (10)	0.0007 (8)	0.0155 (8)	0.0032 (8)
C7	0.0609 (14)	0.0813 (16)	0.0628 (14)	−0.0048 (12)	0.0203 (12)	−0.0189 (12)
C9	0.0537 (14)	0.0697 (15)	0.0981 (19)	−0.0016 (11)	0.0374 (13)	0.0114 (14)
C10	0.0421 (10)	0.0479 (11)	0.0482 (11)	0.0011 (8)	0.0155 (9)	0.0036 (9)
C11	0.0695 (14)	0.0515 (12)	0.0513 (12)	−0.0003 (10)	0.0242 (11)	0.0054 (9)
C12	0.0714 (15)	0.0634 (14)	0.0540 (13)	0.0008 (11)	0.0247 (11)	−0.0052 (11)
C13	0.0644 (14)	0.0496 (12)	0.0752 (16)	0.0025 (10)	0.0268 (12)	−0.0054 (11)
C14	0.0946 (19)	0.0473 (13)	0.0759 (17)	0.0084 (12)	0.0297 (14)	0.0120 (12)
C15	0.0780 (16)	0.0575 (13)	0.0522 (13)	0.0060 (11)	0.0214 (11)	0.0102 (10)
C17	0.0438 (11)	0.0614 (13)	0.0490 (11)	0.0031 (9)	0.0184 (9)	−0.0062 (10)
C19	0.0463 (13)	0.0713 (15)	0.0906 (18)	−0.0025 (11)	0.0267 (12)	−0.0075 (13)
C20	0.0502 (15)	0.136 (3)	0.0838 (19)	−0.0066 (15)	0.0283 (14)	−0.0043 (18)
C21	0.0496 (11)	0.0448 (10)	0.0566 (12)	−0.0021 (9)	0.0248 (10)	0.0051 (9)
C22	0.0548 (13)	0.0563 (12)	0.0637 (14)	0.0058 (10)	0.0273 (11)	0.0052 (11)
C23	0.0582 (13)	0.0618 (13)	0.0651 (14)	0.0022 (11)	0.0199 (11)	0.0116 (11)
C24	0.0695 (15)	0.0561 (12)	0.0547 (13)	−0.0089 (11)	0.0261 (11)	0.0063 (10)
C25	0.0763 (16)	0.0662 (15)	0.0659 (15)	0.0037 (12)	0.0396 (13)	0.0048 (12)
C26	0.0577 (13)	0.0656 (14)	0.0630 (14)	0.0114 (10)	0.0303 (11)	0.0086 (11)

Cl16—C13	1.741 (3)	C22—C23	1.387 (3)
Cl27—C24	1.740 (2)	C23—C24	1.367 (4)
O8—C4	1.209 (3)	C24—C25	1.374 (4)
O18—C17	1.229 (3)	C25—C26	1.380 (3)
N1—C2	1.480 (3)	C2—H2	0.9800
N1—C6	1.480 (3)	C3—H3	0.9800
N1—C17	1.363 (3)	C5—H5	0.9800
C2—C3	1.531 (3)	C6—H6	0.9800
C2—C21	1.531 (3)	C7—H7A	0.9600
C3—C4	1.502 (3)	C7—H7B	0.9600
C3—C7	1.531 (3)	C7—H7C	0.9600
C4—C5	1.515 (3)	C9—H9A	0.9600
C5—C6	1.541 (3)	C9—H9B	0.9600
C5—C9	1.522 (3)	C9—H9C	0.9600
C6—C10	1.517 (3)	C11—H11	0.9300
C10—C11	1.383 (3)	C12—H12	0.9300
C10—C15	1.381 (3)	C14—H14	0.9300
C11—C12	1.381 (3)	C15—H15	0.9300
C12—C13	1.365 (3)	C19—H19	0.9300
C13—C14	1.365 (4)	C20—H20A	0.9300
C14—C15	1.383 (3)	C20—H20B	0.9300
C17—C19	1.482 (3)	C22—H22	0.9300
C19—C20	1.286 (4)	C23—H23	0.9300
C21—C22	1.384 (3)	C25—H25	0.9300
C21—C26	1.389 (3)	C26—H26	0.9300
C2—N1—C6	118.73 (16)	C21—C2—H2	106.00
C2—N1—C17	124.27 (17)	C2—C3—H3	108.00
C6—N1—C17	114.92 (16)	C4—C3—H3	108.00
N1—C2—C3	109.06 (16)	C7—C3—H3	108.00
N1—C2—C21	112.06 (16)	C4—C5—H5	107.00
C3—C2—C21	116.68 (18)	C6—C5—H5	107.00
C2—C3—C4	111.79 (17)	C9—C5—H5	107.00
C2—C3—C7	111.59 (18)	N1—C6—H6	108.00
C4—C3—C7	108.85 (17)	C5—C6—H6	108.00
O8—C4—C3	121.2 (2)	C10—C6—H6	108.00
O8—C4—C5	122.2 (2)	C3—C7—H7A	109.00
C3—C4—C5	116.64 (18)	C3—C7—H7B	109.00
C4—C5—C6	112.65 (17)	C3—C7—H7C	109.00
C4—C5—C9	112.55 (19)	H7A—C7—H7B	109.00
C6—C5—C9	110.90 (17)	H7A—C7—H7C	109.00
N1—C6—C5	112.19 (16)	H7B—C7—H7C	109.00
N1—C6—C10	112.04 (17)	C5—C9—H9A	110.00
C5—C6—C10	109.39 (16)	C5—C9—H9B	109.00
C6—C10—C11	121.58 (18)	C5—C9—H9C	109.00
C6—C10—C15	120.58 (18)	H9A—C9—H9B	109.00
C11—C10—C15	117.71 (19)	H9A—C9—H9C	109.00
C10—C11—C12	121.55 (19)	H9B—C9—H9C	109.00
C11—C12—C13	119.1 (2)	C10—C11—H11	119.00
Cl16—C13—C12	119.3 (2)	C12—C11—H11	119.00
Cl16—C13—C14	119.65 (18)	C11—C12—H12	120.00
C12—C13—C14	121.0 (2)	C13—C12—H12	120.00
C13—C14—C15	119.4 (2)	C13—C14—H14	120.00
C10—C15—C14	121.2 (2)	C15—C14—H14	120.00
O18—C17—N1	120.6 (2)	C10—C15—H15	119.00
O18—C17—C19	120.0 (2)	C14—C15—H15	119.00
N1—C17—C19	119.40 (19)	C17—C19—H19	119.00
C17—C19—C20	121.4 (3)	C20—C19—H19	119.00
C2—C21—C22	123.55 (19)	C19—C20—H20A	120.00
C2—C21—C26	118.78 (19)	C19—C20—H20B	120.00
C22—C21—C26	117.61 (19)	H20A—C20—H20B	120.00
C21—C22—C23	121.1 (2)	C21—C22—H22	119.00
C22—C23—C24	119.6 (2)	C23—C22—H22	120.00
Cl27—C24—C23	119.7 (2)	C22—C23—H23	120.00
Cl27—C24—C25	119.3 (2)	C24—C23—H23	120.00
C23—C24—C25	121.0 (2)	C24—C25—H25	121.00
C24—C25—C26	118.8 (2)	C26—C25—H25	121.00
C21—C26—C25	121.9 (2)	C21—C26—H26	119.00
N1—C2—H2	106.00	C25—C26—H26	119.00
C3—C2—H2	106.00
C6—N1—C2—C3	−46.8 (2)	C4—C5—C6—C10	171.32 (17)
C6—N1—C2—C21	83.9 (2)	C9—C5—C6—N1	173.51 (18)
C17—N1—C2—C3	115.9 (2)	C9—C5—C6—C10	−61.5 (2)
C17—N1—C2—C21	−113.4 (2)	N1—C6—C10—C11	59.9 (3)
C2—N1—C6—C5	−4.6 (2)	N1—C6—C10—C15	−124.3 (2)
C2—N1—C6—C10	−128.09 (18)	C5—C6—C10—C11	−65.2 (3)
C17—N1—C6—C5	−168.89 (17)	C5—C6—C10—C15	110.6 (2)
C17—N1—C6—C10	67.6 (2)	C6—C10—C11—C12	174.6 (2)
C2—N1—C17—O18	−166.34 (19)	C15—C10—C11—C12	−1.3 (3)
C2—N1—C17—C19	15.5 (3)	C6—C10—C15—C14	−174.9 (3)
C6—N1—C17—O18	−3.0 (3)	C11—C10—C15—C14	1.0 (4)
C6—N1—C17—C19	178.84 (19)	C10—C11—C12—C13	0.6 (3)
N1—C2—C3—C4	56.9 (2)	C11—C12—C13—Cl16	−178.46 (18)
N1—C2—C3—C7	−65.3 (2)	C11—C12—C13—C14	0.5 (4)
C21—C2—C3—C4	−71.3 (2)	Cl16—C13—C14—C15	178.2 (2)
C21—C2—C3—C7	166.51 (18)	C12—C13—C14—C15	−0.8 (4)
N1—C2—C21—C22	−130.3 (2)	C13—C14—C15—C10	0.0 (5)
N1—C2—C21—C26	52.7 (3)	O18—C17—C19—C20	1.8 (4)
C3—C2—C21—C22	−3.5 (3)	N1—C17—C19—C20	179.9 (3)
C3—C2—C21—C26	179.44 (19)	C2—C21—C22—C23	−177.7 (2)
C2—C3—C4—O8	163.9 (2)	C26—C21—C22—C23	−0.7 (3)
C2—C3—C4—C5	−16.1 (2)	C2—C21—C26—C25	177.8 (2)
C7—C3—C4—O8	−72.4 (3)	C22—C21—C26—C25	0.6 (3)
C7—C3—C4—C5	107.6 (2)	C21—C22—C23—C24	0.0 (3)
O8—C4—C5—C6	144.5 (2)	C22—C23—C24—Cl27	−179.46 (18)
O8—C4—C5—C9	18.3 (3)	C22—C23—C24—C25	0.8 (4)
C3—C4—C5—C6	−35.4 (2)	Cl27—C24—C25—C26	179.38 (19)
C3—C4—C5—C9	−161.70 (19)	C23—C24—C25—C26	−0.8 (4)
C4—C5—C6—N1	46.3 (2)	C24—C25—C26—C21	0.2 (4)