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

In the title compound, C(21)H(20)Cl(3)NO(2), the piperidin-4-one ring adopts a boat conformation. The two 2-chloro-phenyl groups are approximately perpendicular to each other, making a dihedral angle of 74.07 (8)°.

Related literature

For the biological activity of related structures, see: Parthiban et al. (2009 ▶); Aridoss et al. (2007 ▶). For spectroscopic studies of piperidin-4-ones, see: Ravindran et al. (1991 ▶); Krishnakumar et al. (1996 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For the synthesis of the title compound, see: Ramachandran et al. (2008 ▶); Aridoss et al. (2010 ▶).

Experimental

Crystal data

C21H20Cl3NO2

M = 424.73

Monoclinic,

a = 11.6295 (4) Å

b = 9.6955 (3) Å

c = 17.4743 (5) Å

β = 90.481 (1)°

V = 1970.22 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.22 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.901, T max = 0.927

27536 measured reflections

6864 independent reflections

4998 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.141

S = 1.01

6864 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810031247/ez2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031247/ez2226Isup2.hkl

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

C21H20Cl3NO2	F(000) = 880
Mr = 424.73	Dx = 1.432 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5467 reflections
a = 11.6295 (4) Å	θ = 2.1–25.0°
b = 9.6955 (3) Å	µ = 0.48 mm−1
c = 17.4743 (5) Å	T = 293 K
β = 90.481 (1)°	Prism, colourless
V = 1970.22 (11) Å3	0.22 × 0.16 × 0.16 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	6864 independent reflections
Radiation source: fine-focus sealed tube	4998 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scan	θmax = 32.1°, θmin = 2.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −17→17
Tmin = 0.901, Tmax = 0.927	k = −14→14
27536 measured reflections	l = −26→26

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.5226P] where P = (Fo2 + 2Fc2)/3
6864 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.31 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	0.85514 (12)	0.37161 (13)	−0.00740 (8)	0.0341 (3)
H1A	0.8746	0.4692	−0.0004	0.041*
C2	0.96025 (12)	0.30363 (15)	−0.04343 (8)	0.0385 (3)
H2A	1.0237	0.3032	−0.0062	0.046*
C3	0.93368 (13)	0.15720 (15)	−0.06701 (9)	0.0415 (3)
C4	0.80789 (13)	0.11575 (13)	−0.07058 (8)	0.0368 (3)
H4A	0.7839	0.0981	−0.0178	0.044*
C5	0.73061 (12)	0.23387 (13)	−0.10157 (7)	0.0340 (2)
H5A	0.7456	0.2437	−0.1564	0.041*
C6	0.82292 (12)	0.31664 (14)	0.07135 (7)	0.0346 (3)
C7	0.73896 (13)	0.37879 (15)	0.11624 (8)	0.0393 (3)
C8	0.70953 (16)	0.32934 (19)	0.18766 (9)	0.0505 (4)
H8A	0.6519	0.3724	0.2155	0.061*
C9	0.76589 (18)	0.2157 (2)	0.21762 (9)	0.0562 (4)
H9A	0.7457	0.1810	0.2653	0.067*
C10	0.85181 (17)	0.15487 (18)	0.17638 (10)	0.0529 (4)
H10A	0.8911	0.0794	0.1965	0.063*
C11	0.88047 (14)	0.20513 (16)	0.10491 (9)	0.0432 (3)
H11A	0.9400	0.1633	0.0783	0.052*
C12	0.99879 (15)	0.37953 (19)	−0.11617 (10)	0.0494 (4)
H12A	1.0647	0.3339	−0.1371	0.074*
H12B	1.0184	0.4731	−0.1036	0.074*
H12C	0.9373	0.3790	−0.1532	0.074*
C13	0.79149 (17)	−0.01856 (16)	−0.11449 (11)	0.0516 (4)
H13A	0.8409	−0.0882	−0.0931	0.077*
H13B	0.8104	−0.0044	−0.1673	0.077*
H13C	0.7129	−0.0478	−0.1108	0.077*
C14	0.60451 (13)	0.19672 (14)	−0.09241 (8)	0.0380 (3)
C15	0.53718 (15)	0.14574 (17)	−0.15177 (10)	0.0491 (4)
C16	0.42350 (17)	0.1070 (2)	−0.14119 (13)	0.0619 (5)
H16A	0.3809	0.0702	−0.1816	0.074*
C17	0.37424 (16)	0.12352 (19)	−0.07036 (14)	0.0614 (5)
H17A	0.2978	0.0989	−0.0630	0.074*
C18	0.43777 (16)	0.17623 (19)	−0.01064 (12)	0.0548 (4)
H18A	0.4041	0.1889	0.0369	0.066*
C19	0.55201 (14)	0.21042 (16)	−0.02132 (9)	0.0432 (3)
H19A	0.5949	0.2434	0.0199	0.052*
C20	0.73202 (12)	0.49115 (14)	−0.09783 (8)	0.0379 (3)
C21	0.63849 (16)	0.48474 (18)	−0.15890 (10)	0.0514 (4)
H21A	0.5701	0.4434	−0.1374	0.062*
H21B	0.6640	0.4265	−0.2006	0.062*
O1	1.01004 (12)	0.07846 (14)	−0.08337 (10)	0.0692 (4)
O2	0.77569 (11)	0.59995 (11)	−0.07971 (7)	0.0528 (3)
N1	0.75946 (10)	0.36719 (11)	−0.06397 (6)	0.0326 (2)
Cl1	0.66924 (4)	0.52622 (4)	0.08431 (3)	0.05574 (13)
Cl2	0.59251 (5)	0.13268 (7)	−0.24418 (3)	0.07505 (18)
Cl3	0.60408 (4)	0.64954 (5)	−0.19502 (3)	0.06205 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0384 (6)	0.0286 (6)	0.0353 (6)	0.0014 (5)	−0.0026 (5)	0.0020 (4)
C2	0.0353 (6)	0.0382 (7)	0.0421 (7)	0.0015 (5)	0.0007 (5)	0.0047 (5)
C3	0.0434 (7)	0.0362 (7)	0.0452 (7)	0.0071 (6)	0.0061 (6)	0.0042 (5)
C4	0.0440 (7)	0.0285 (6)	0.0379 (6)	0.0028 (5)	0.0056 (5)	−0.0003 (5)
C5	0.0386 (6)	0.0313 (6)	0.0320 (6)	0.0013 (5)	0.0025 (5)	−0.0023 (4)
C6	0.0407 (6)	0.0305 (6)	0.0325 (6)	0.0025 (5)	−0.0022 (5)	−0.0009 (5)
C7	0.0441 (7)	0.0364 (6)	0.0373 (6)	0.0048 (5)	−0.0030 (5)	−0.0051 (5)
C8	0.0543 (9)	0.0583 (9)	0.0390 (7)	0.0055 (7)	0.0056 (7)	−0.0077 (7)
C9	0.0723 (11)	0.0619 (10)	0.0345 (7)	0.0008 (9)	0.0044 (7)	0.0058 (7)
C10	0.0677 (11)	0.0490 (9)	0.0419 (8)	0.0094 (8)	−0.0027 (7)	0.0106 (6)
C11	0.0509 (8)	0.0402 (7)	0.0386 (7)	0.0104 (6)	−0.0005 (6)	0.0041 (6)
C12	0.0462 (8)	0.0539 (9)	0.0482 (8)	−0.0054 (7)	0.0069 (7)	0.0089 (7)
C13	0.0646 (10)	0.0333 (7)	0.0571 (9)	0.0017 (7)	0.0077 (8)	−0.0078 (6)
C14	0.0404 (7)	0.0328 (6)	0.0410 (7)	−0.0012 (5)	0.0011 (5)	−0.0040 (5)
C15	0.0493 (8)	0.0474 (8)	0.0504 (8)	−0.0004 (7)	−0.0060 (7)	−0.0089 (7)
C16	0.0525 (10)	0.0523 (10)	0.0804 (13)	−0.0082 (8)	−0.0200 (9)	−0.0034 (9)
C17	0.0431 (9)	0.0483 (9)	0.0929 (15)	−0.0075 (7)	0.0031 (9)	0.0139 (9)
C18	0.0503 (9)	0.0458 (8)	0.0686 (11)	−0.0028 (7)	0.0156 (8)	0.0093 (8)
C19	0.0464 (8)	0.0377 (7)	0.0455 (7)	−0.0033 (6)	0.0074 (6)	−0.0003 (6)
C20	0.0412 (7)	0.0346 (6)	0.0379 (6)	0.0049 (5)	0.0015 (5)	0.0057 (5)
C21	0.0559 (9)	0.0466 (8)	0.0516 (9)	0.0061 (7)	−0.0126 (7)	0.0126 (7)
O1	0.0535 (7)	0.0504 (7)	0.1039 (12)	0.0162 (6)	0.0167 (7)	−0.0077 (7)
O2	0.0664 (8)	0.0322 (5)	0.0596 (7)	−0.0005 (5)	−0.0111 (6)	0.0084 (5)
N1	0.0375 (5)	0.0277 (5)	0.0325 (5)	0.0015 (4)	−0.0017 (4)	0.0018 (4)
Cl1	0.0653 (3)	0.0465 (2)	0.0555 (2)	0.02331 (18)	0.00334 (19)	−0.00359 (17)
Cl2	0.0761 (3)	0.1018 (4)	0.0471 (2)	0.0034 (3)	−0.0109 (2)	−0.0279 (2)
Cl3	0.0654 (3)	0.0601 (3)	0.0607 (3)	0.0222 (2)	−0.0028 (2)	0.0202 (2)

C1—N1	1.4828 (17)	C11—H11A	0.9300
C1—C6	1.5253 (18)	C12—H12A	0.9600
C1—C2	1.5291 (19)	C12—H12B	0.9600
C1—H1A	0.9800	C12—H12C	0.9600
C2—C3	1.510 (2)	C13—H13A	0.9600
C2—C12	1.539 (2)	C13—H13B	0.9600
C2—H2A	0.9800	C13—H13C	0.9600
C3—O1	1.2072 (18)	C14—C15	1.386 (2)
C3—C4	1.518 (2)	C14—C19	1.395 (2)
C4—C13	1.523 (2)	C15—C16	1.388 (3)
C4—C5	1.5506 (19)	C15—Cl2	1.7480 (19)
C4—H4A	0.9800	C16—C17	1.378 (3)
C5—N1	1.4871 (17)	C16—H16A	0.9300
C5—C14	1.520 (2)	C17—C18	1.372 (3)
C5—H5A	0.9800	C17—H17A	0.9300
C6—C7	1.3946 (19)	C18—C19	1.383 (2)
C6—C11	1.3979 (19)	C18—H18A	0.9300
C7—C8	1.383 (2)	C19—H19A	0.9300
C7—Cl1	1.7333 (15)	C20—O2	1.2117 (19)
C8—C9	1.382 (3)	C20—N1	1.3760 (16)
C8—H8A	0.9300	C20—C21	1.519 (2)
C9—C10	1.370 (3)	C21—Cl3	1.7628 (16)
C9—H9A	0.9300	C21—H21A	0.9700
C10—C11	1.384 (2)	C21—H21B	0.9700
C10—H10A	0.9300
N1—C1—C6	113.75 (11)	C6—C11—H11A	118.9
N1—C1—C2	108.12 (11)	C2—C12—H12A	109.5
C6—C1—C2	115.10 (11)	C2—C12—H12B	109.5
N1—C1—H1A	106.4	H12A—C12—H12B	109.5
C6—C1—H1A	106.4	C2—C12—H12C	109.5
C2—C1—H1A	106.4	H12A—C12—H12C	109.5
C3—C2—C1	110.81 (12)	H12B—C12—H12C	109.5
C3—C2—C12	106.54 (13)	C4—C13—H13A	109.5
C1—C2—C12	111.93 (12)	C4—C13—H13B	109.5
C3—C2—H2A	109.2	H13A—C13—H13B	109.5
C1—C2—H2A	109.2	C4—C13—H13C	109.5
C12—C2—H2A	109.2	H13A—C13—H13C	109.5
O1—C3—C2	120.67 (15)	H13B—C13—H13C	109.5
O1—C3—C4	122.25 (15)	C15—C14—C19	116.86 (14)
C2—C3—C4	117.08 (12)	C15—C14—C5	123.05 (13)
C3—C4—C13	111.32 (13)	C19—C14—C5	120.08 (13)
C3—C4—C5	111.98 (11)	C14—C15—C16	121.98 (17)
C13—C4—C5	112.70 (13)	C14—C15—Cl2	120.50 (13)
C3—C4—H4A	106.8	C16—C15—Cl2	117.50 (14)
C13—C4—H4A	106.8	C17—C16—C15	119.46 (18)
C5—C4—H4A	106.8	C17—C16—H16A	120.3
N1—C5—C14	111.94 (10)	C15—C16—H16A	120.3
N1—C5—C4	111.08 (11)	C18—C17—C16	120.09 (17)
C14—C5—C4	110.19 (11)	C18—C17—H17A	120.0
N1—C5—H5A	107.8	C16—C17—H17A	120.0
C14—C5—H5A	107.8	C17—C18—C19	119.88 (18)
C4—C5—H5A	107.8	C17—C18—H18A	120.1
C7—C6—C11	115.67 (13)	C19—C18—H18A	120.1
C7—C6—C1	122.34 (12)	C18—C19—C14	121.68 (16)
C11—C6—C1	121.90 (12)	C18—C19—H19A	119.2
C8—C7—C6	122.53 (14)	C14—C19—H19A	119.2
C8—C7—Cl1	117.25 (12)	O2—C20—N1	123.57 (13)
C6—C7—Cl1	120.20 (11)	O2—C20—C21	121.02 (13)
C9—C8—C7	119.87 (15)	N1—C20—C21	115.37 (13)
C9—C8—H8A	120.1	C20—C21—Cl3	111.94 (12)
C7—C8—H8A	120.1	C20—C21—H21A	109.2
C10—C9—C8	119.31 (15)	Cl3—C21—H21A	109.2
C10—C9—H9A	120.3	C20—C21—H21B	109.2
C8—C9—H9A	120.3	Cl3—C21—H21B	109.2
C9—C10—C11	120.33 (16)	H21A—C21—H21B	107.9
C9—C10—H10A	119.8	C20—N1—C1	115.56 (11)
C11—C10—H10A	119.8	C20—N1—C5	121.24 (11)
C10—C11—C6	122.20 (15)	C1—N1—C5	119.01 (10)
C10—C11—H11A	118.9
N1—C1—C2—C3	−58.03 (14)	C1—C6—C11—C10	179.89 (15)
C6—C1—C2—C3	70.37 (15)	N1—C5—C14—C15	136.19 (14)
N1—C1—C2—C12	60.74 (15)	C4—C5—C14—C15	−99.67 (16)
C6—C1—C2—C12	−170.85 (12)	N1—C5—C14—C19	−45.29 (17)
C1—C2—C3—O1	−166.27 (15)	C4—C5—C14—C19	78.86 (16)
C12—C2—C3—O1	71.75 (19)	C19—C14—C15—C16	−1.4 (2)
C1—C2—C3—C4	14.92 (17)	C5—C14—C15—C16	177.20 (16)
C12—C2—C3—C4	−107.06 (14)	C19—C14—C15—Cl2	176.79 (12)
O1—C3—C4—C13	−13.9 (2)	C5—C14—C15—Cl2	−4.6 (2)
C2—C3—C4—C13	164.91 (13)	C14—C15—C16—C17	2.2 (3)
O1—C3—C4—C5	−141.05 (16)	Cl2—C15—C16—C17	−176.06 (15)
C2—C3—C4—C5	37.74 (17)	C15—C16—C17—C18	−0.8 (3)
C3—C4—C5—N1	−46.40 (15)	C16—C17—C18—C19	−1.2 (3)
C13—C4—C5—N1	−172.84 (12)	C17—C18—C19—C14	2.0 (3)
C3—C4—C5—C14	−171.04 (11)	C15—C14—C19—C18	−0.7 (2)
C13—C4—C5—C14	62.52 (15)	C5—C14—C19—C18	−179.31 (14)
N1—C1—C6—C7	−62.84 (17)	O2—C20—C21—Cl3	−1.2 (2)
C2—C1—C6—C7	171.62 (13)	N1—C20—C21—Cl3	176.76 (11)
N1—C1—C6—C11	120.85 (14)	O2—C20—N1—C1	−5.4 (2)
C2—C1—C6—C11	−4.69 (19)	C21—C20—N1—C1	176.75 (13)
C11—C6—C7—C8	−3.4 (2)	O2—C20—N1—C5	−162.10 (14)
C1—C6—C7—C8	−179.97 (14)	C21—C20—N1—C5	20.01 (19)
C11—C6—C7—Cl1	174.97 (12)	C6—C1—N1—C20	123.99 (12)
C1—C6—C7—Cl1	−1.55 (19)	C2—C1—N1—C20	−106.85 (13)
C6—C7—C8—C9	1.4 (3)	C6—C1—N1—C5	−78.72 (14)
Cl1—C7—C8—C9	−177.11 (14)	C2—C1—N1—C5	50.45 (14)
C7—C8—C9—C10	1.0 (3)	C14—C5—N1—C20	−78.22 (15)
C8—C9—C10—C11	−1.1 (3)	C4—C5—N1—C20	158.14 (12)
C9—C10—C11—C6	−1.2 (3)	C14—C5—N1—C1	125.81 (12)
C7—C6—C11—C10	3.4 (2)	C4—C5—N1—C1	2.17 (16)