1-Dichloro-acetyl-r-2,c-6-bis-(4-methoxy-phen-yl)-t-3-methyl-piperidin-4-one.

In the title compound, C(22)H(23)Cl(2)NO(4), the piperidine ring adopts a distorted boat conformation. The meth-oxy groups lie in the plane of the benzene rings to which they are attached. The benzene rings are oriented at angles of 84.3 (1) and 76.8 (1)° with respect to the best plane through the piperidine ring. The crystal packing is stabilized by intermolecular C-H⋯O inter-actions.

Related literature

For general background to piperidine derivatives, see: Perumal et al. (2001 ▶); Dimmock et al. (2001 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H23Cl2NO4

M = 436.31

Monoclinic,

a = 19.3021 (16) Å

b = 10.5886 (9) Å

c = 10.3241 (10) Å

β = 91.445 (5)°

V = 2109.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.25 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.919, T max = 0.926

17272 measured reflections

5140 independent reflections

2632 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.210

S = 1.05

5140 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054713/bt5145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054713/bt5145Isup2.hkl

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

C22H23Cl2NO4	F(000) = 912
Mr = 436.31	Dx = 1.374 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2564 reflections
a = 19.3021 (16) Å	θ = 1.1–28.7°
b = 10.5886 (9) Å	µ = 0.34 mm−1
c = 10.3241 (10) Å	T = 293 K
β = 91.445 (5)°	Block, colorless
V = 2109.4 (3) Å3	0.25 × 0.24 × 0.23 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5140 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω and φ scans	θmax = 28.7°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −25→25
Tmin = 0.919, Tmax = 0.926	k = −13→14
17272 measured reflections	l = −13→10

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1035P)2 + 0.3613P] where P = (Fo2 + 2Fc2)/3
5140 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.34 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
Cl1	0.06236 (4)	0.37763 (8)	0.02208 (10)	0.0600 (3)
Cl2	0.10261 (5)	0.12850 (8)	−0.06850 (10)	0.0618 (3)
O1	0.18680 (12)	0.2296 (2)	0.1496 (2)	0.0611 (7)
O2	0.37098 (13)	0.6870 (3)	0.4740 (3)	0.0714 (8)
O3	0.43242 (15)	0.3729 (4)	−0.1711 (4)	0.1125 (13)
O4	0.06912 (12)	0.8442 (2)	−0.1071 (3)	0.0607 (7)
N1	0.24905 (12)	0.3470 (2)	0.0117 (2)	0.0378 (6)
C2	0.31270 (15)	0.3183 (3)	0.0888 (3)	0.0433 (8)
H2	0.3025	0.2422	0.1388	0.052*
C3	0.36826 (17)	0.2806 (3)	−0.0059 (4)	0.0568 (9)
H3A	0.4110	0.2633	0.0423	0.068*
H3B	0.3541	0.2032	−0.0493	0.068*
C4	0.38194 (18)	0.3784 (4)	−0.1054 (4)	0.0617 (10)
C5	0.32820 (16)	0.4799 (3)	−0.1204 (3)	0.0481 (8)
H5	0.3364	0.5402	−0.0496	0.058*
C6	0.25383 (14)	0.4284 (3)	−0.1064 (3)	0.0379 (7)
H6	0.2431	0.3755	−0.1821	0.046*
C7	0.19106 (15)	0.2871 (3)	0.0469 (3)	0.0407 (7)
C8	0.12870 (15)	0.2872 (3)	−0.0465 (3)	0.0413 (7)
H8	0.1416	0.3238	−0.1297	0.050*
C9	0.33116 (14)	0.4193 (3)	0.1869 (3)	0.0424 (7)
C10	0.28014 (16)	0.4676 (3)	0.2662 (3)	0.0502 (8)
H10	0.2348	0.4393	0.2548	0.060*
C11	0.29471 (17)	0.5556 (4)	0.3605 (3)	0.0562 (9)
H11	0.2595	0.5863	0.4117	0.067*
C12	0.36200 (18)	0.5987 (3)	0.3792 (3)	0.0530 (9)
C13	0.41367 (17)	0.5519 (4)	0.3030 (4)	0.0584 (10)
H13	0.4591	0.5795	0.3151	0.070*
C14	0.39748 (16)	0.4635 (4)	0.2082 (3)	0.0543 (9)
H14	0.4327	0.4328	0.1571	0.065*
C15	0.4393 (2)	0.7283 (4)	0.5030 (5)	0.0878 (14)
H15A	0.4678	0.6569	0.5255	0.132*
H15B	0.4389	0.7863	0.5744	0.132*
H15C	0.4577	0.7698	0.4286	0.132*
C16	0.3347 (2)	0.5526 (4)	−0.2460 (4)	0.0691 (11)
H16A	0.3821	0.5770	−0.2566	0.104*
H16B	0.3061	0.6267	−0.2436	0.104*
H16C	0.3199	0.5001	−0.3173	0.104*
C17	0.20227 (14)	0.5359 (3)	−0.1064 (3)	0.0348 (7)
C18	0.15426 (15)	0.5514 (3)	−0.2067 (3)	0.0399 (7)
H18	0.1529	0.4928	−0.2738	0.048*
C19	0.10828 (16)	0.6511 (3)	−0.2103 (3)	0.0428 (7)
H19	0.0759	0.6581	−0.2781	0.051*
C20	0.11057 (16)	0.7406 (3)	−0.1126 (3)	0.0425 (7)
C21	0.15861 (16)	0.7270 (3)	−0.0128 (3)	0.0456 (8)
H21	0.1608	0.7871	0.0528	0.055*
C22	0.20341 (16)	0.6263 (3)	−0.0083 (3)	0.0419 (7)
H22	0.2348	0.6183	0.0610	0.050*
C23	0.0234 (2)	0.8678 (3)	−0.2145 (5)	0.0703 (11)
H23A	0.0497	0.8761	−0.2917	0.105*
H23B	−0.0018	0.9444	−0.1999	0.105*
H23C	−0.0085	0.7987	−0.2243	0.105*

	U11	U22	U33	U12	U13	U23
Cl1	0.0590 (5)	0.0573 (5)	0.0641 (7)	0.0081 (4)	0.0103 (4)	0.0020 (4)
Cl2	0.0749 (6)	0.0441 (5)	0.0665 (7)	−0.0149 (4)	0.0003 (5)	−0.0053 (4)
O1	0.0674 (15)	0.0703 (16)	0.0452 (15)	−0.0148 (12)	−0.0051 (12)	0.0270 (13)
O2	0.0731 (17)	0.0837 (18)	0.0570 (18)	−0.0107 (14)	−0.0054 (14)	−0.0164 (15)
O3	0.0646 (18)	0.161 (3)	0.114 (3)	0.0281 (19)	0.0481 (19)	0.042 (2)
O4	0.0657 (15)	0.0398 (12)	0.076 (2)	0.0079 (11)	−0.0022 (14)	−0.0061 (12)
N1	0.0424 (13)	0.0422 (14)	0.0288 (15)	0.0000 (11)	0.0011 (11)	0.0049 (11)
C2	0.0434 (17)	0.0500 (18)	0.037 (2)	0.0071 (14)	−0.0012 (14)	0.0052 (15)
C3	0.0512 (19)	0.068 (2)	0.051 (2)	0.0129 (17)	0.0018 (16)	−0.0085 (19)
C4	0.0458 (19)	0.088 (3)	0.052 (2)	−0.0024 (18)	0.0091 (17)	−0.006 (2)
C5	0.0497 (18)	0.058 (2)	0.037 (2)	−0.0090 (15)	0.0100 (14)	−0.0009 (16)
C6	0.0457 (16)	0.0459 (17)	0.0223 (16)	−0.0058 (13)	0.0028 (12)	−0.0004 (13)
C7	0.0467 (17)	0.0386 (16)	0.0367 (19)	−0.0007 (13)	0.0002 (14)	0.0030 (14)
C8	0.0463 (16)	0.0394 (15)	0.0382 (19)	−0.0059 (13)	0.0011 (14)	0.0018 (13)
C9	0.0397 (16)	0.0568 (19)	0.0307 (18)	0.0009 (14)	−0.0018 (13)	0.0029 (15)
C10	0.0420 (17)	0.068 (2)	0.041 (2)	−0.0006 (15)	−0.0010 (14)	−0.0059 (17)
C11	0.0478 (19)	0.077 (2)	0.043 (2)	0.0032 (17)	0.0017 (15)	−0.0102 (19)
C12	0.060 (2)	0.065 (2)	0.033 (2)	−0.0035 (17)	−0.0043 (16)	−0.0014 (17)
C13	0.0459 (19)	0.083 (3)	0.046 (2)	−0.0115 (18)	−0.0030 (16)	0.001 (2)
C14	0.0411 (17)	0.083 (3)	0.038 (2)	−0.0005 (17)	0.0037 (14)	−0.0004 (19)
C15	0.086 (3)	0.098 (3)	0.078 (3)	−0.025 (3)	−0.013 (3)	−0.022 (3)
C16	0.079 (3)	0.078 (3)	0.051 (3)	−0.019 (2)	0.019 (2)	0.010 (2)
C17	0.0474 (16)	0.0344 (15)	0.0228 (16)	−0.0052 (12)	0.0054 (12)	0.0021 (12)
C18	0.0579 (18)	0.0344 (15)	0.0276 (18)	−0.0022 (13)	0.0029 (14)	−0.0015 (13)
C19	0.0543 (18)	0.0383 (16)	0.0356 (19)	−0.0048 (13)	−0.0026 (14)	0.0099 (14)
C20	0.0512 (17)	0.0336 (16)	0.043 (2)	−0.0036 (13)	0.0078 (15)	0.0030 (14)
C21	0.0567 (18)	0.0443 (17)	0.036 (2)	−0.0033 (15)	0.0074 (15)	−0.0106 (15)
C22	0.0478 (17)	0.0485 (18)	0.0294 (18)	−0.0010 (14)	−0.0010 (13)	−0.0004 (14)
C23	0.068 (2)	0.051 (2)	0.090 (3)	0.0093 (18)	−0.012 (2)	0.014 (2)

Cl1—C8	1.762 (3)	C10—C11	1.372 (5)
Cl2—C8	1.768 (3)	C10—H10	0.9300
O1—C7	1.228 (4)	C11—C12	1.385 (4)
O2—C12	1.362 (4)	C11—H11	0.9300
O2—C15	1.415 (4)	C12—C13	1.378 (5)
O3—C4	1.203 (4)	C13—C14	1.383 (5)
O4—C20	1.360 (4)	C13—H13	0.9300
O4—C23	1.422 (4)	C14—H14	0.9300
N1—C7	1.344 (4)	C15—H15A	0.9600
N1—C2	1.479 (4)	C15—H15B	0.9600
N1—C6	1.498 (4)	C15—H15C	0.9600
C2—C9	1.509 (4)	C16—H16A	0.9600
C2—C3	1.523 (4)	C16—H16B	0.9600
C2—H2	0.9800	C16—H16C	0.9600
C3—C4	1.487 (5)	C17—C18	1.382 (4)
C3—H3A	0.9700	C17—C22	1.394 (4)
C3—H3B	0.9700	C18—C19	1.379 (4)
C4—C5	1.499 (5)	C18—H18	0.9300
C5—C16	1.516 (5)	C19—C20	1.384 (4)
C5—C6	1.546 (4)	C19—H19	0.9300
C5—H5	0.9800	C20—C21	1.377 (4)
C6—C17	1.512 (4)	C21—C22	1.372 (4)
C6—H6	0.9800	C21—H21	0.9300
C7—C8	1.523 (4)	C22—H22	0.9300
C8—H8	0.9800	C23—H23A	0.9600
C9—C14	1.375 (4)	C23—H23B	0.9600
C9—C10	1.393 (4)	C23—H23C	0.9600
C12—O2—C15	117.7 (3)	C10—C11—H11	120.1
C20—O4—C23	117.6 (3)	C12—C11—H11	120.1
C7—N1—C2	116.4 (2)	O2—C12—C13	125.2 (3)
C7—N1—C6	124.0 (2)	O2—C12—C11	115.3 (3)
C2—N1—C6	119.3 (2)	C13—C12—C11	119.4 (3)
N1—C2—C9	113.3 (2)	C12—C13—C14	119.5 (3)
N1—C2—C3	107.3 (3)	C12—C13—H13	120.2
C9—C2—C3	117.3 (3)	C14—C13—H13	120.2
N1—C2—H2	106.1	C9—C14—C13	122.4 (3)
C9—C2—H2	106.1	C9—C14—H14	118.8
C3—C2—H2	106.1	C13—C14—H14	118.8
C4—C3—C2	113.6 (3)	O2—C15—H15A	109.5
C4—C3—H3A	108.8	O2—C15—H15B	109.5
C2—C3—H3A	108.8	H15A—C15—H15B	109.5
C4—C3—H3B	108.8	O2—C15—H15C	109.5
C2—C3—H3B	108.8	H15A—C15—H15C	109.5
H3A—C3—H3B	107.7	H15B—C15—H15C	109.5
O3—C4—C3	121.1 (4)	C5—C16—H16A	109.5
O3—C4—C5	123.0 (4)	C5—C16—H16B	109.5
C3—C4—C5	115.9 (3)	H16A—C16—H16B	109.5
C4—C5—C16	112.4 (3)	C5—C16—H16C	109.5
C4—C5—C6	112.3 (3)	H16A—C16—H16C	109.5
C16—C5—C6	110.9 (3)	H16B—C16—H16C	109.5
C4—C5—H5	107.0	C18—C17—C22	117.5 (3)
C16—C5—H5	107.0	C18—C17—C6	121.2 (3)
C6—C5—H5	107.0	C22—C17—C6	121.3 (3)
N1—C6—C17	112.3 (2)	C19—C18—C17	122.0 (3)
N1—C6—C5	110.8 (2)	C19—C18—H18	119.0
C17—C6—C5	110.3 (2)	C17—C18—H18	119.0
N1—C6—H6	107.7	C18—C19—C20	119.7 (3)
C17—C6—H6	107.7	C18—C19—H19	120.1
C5—C6—H6	107.7	C20—C19—H19	120.1
O1—C7—N1	122.8 (3)	O4—C20—C21	116.0 (3)
O1—C7—C8	118.6 (3)	O4—C20—C19	125.1 (3)
N1—C7—C8	118.6 (3)	C21—C20—C19	118.9 (3)
C7—C8—Cl1	108.5 (2)	C22—C21—C20	121.3 (3)
C7—C8—Cl2	107.4 (2)	C22—C21—H21	119.4
Cl1—C8—Cl2	111.14 (16)	C20—C21—H21	119.4
C7—C8—H8	109.9	C21—C22—C17	120.7 (3)
Cl1—C8—H8	109.9	C21—C22—H22	119.7
Cl2—C8—H8	109.9	C17—C22—H22	119.7
C14—C9—C10	116.7 (3)	O4—C23—H23A	109.5
C14—C9—C2	123.5 (3)	O4—C23—H23B	109.5
C10—C9—C2	119.7 (3)	H23A—C23—H23B	109.5
C11—C10—C9	122.1 (3)	O4—C23—H23C	109.5
C11—C10—H10	119.0	H23A—C23—H23C	109.5
C9—C10—H10	119.0	H23B—C23—H23C	109.5
C10—C11—C12	119.8 (3)
C7—N1—C2—C9	−101.3 (3)	N1—C2—C9—C10	46.9 (4)
C6—N1—C2—C9	84.8 (3)	C3—C2—C9—C10	172.8 (3)
C7—N1—C2—C3	127.6 (3)	C14—C9—C10—C11	0.5 (5)
C6—N1—C2—C3	−46.3 (3)	C2—C9—C10—C11	177.3 (3)
N1—C2—C3—C4	57.2 (4)	C9—C10—C11—C12	−0.2 (6)
C9—C2—C3—C4	−71.6 (4)	C15—O2—C12—C13	−4.4 (6)
C2—C3—C4—O3	166.1 (4)	C15—O2—C12—C11	176.0 (3)
C2—C3—C4—C5	−15.7 (4)	C10—C11—C12—O2	179.3 (3)
O3—C4—C5—C16	14.5 (5)	C10—C11—C12—C13	−0.3 (6)
C3—C4—C5—C16	−163.6 (3)	O2—C12—C13—C14	−179.0 (3)
O3—C4—C5—C6	140.2 (4)	C11—C12—C13—C14	0.6 (6)
C3—C4—C5—C6	−37.8 (4)	C10—C9—C14—C13	−0.2 (5)
C7—N1—C6—C17	57.7 (4)	C2—C9—C14—C13	−176.9 (3)
C2—N1—C6—C17	−128.9 (3)	C12—C13—C14—C9	−0.3 (6)
C7—N1—C6—C5	−178.4 (3)	N1—C6—C17—C18	−122.7 (3)
C2—N1—C6—C5	−5.1 (4)	C5—C6—C17—C18	113.1 (3)
C4—C5—C6—N1	48.3 (4)	N1—C6—C17—C22	60.2 (3)
C16—C5—C6—N1	174.9 (3)	C5—C6—C17—C22	−64.0 (3)
C4—C5—C6—C17	173.3 (3)	C22—C17—C18—C19	−0.8 (4)
C16—C5—C6—C17	−60.1 (3)	C6—C17—C18—C19	−178.0 (3)
C2—N1—C7—O1	12.7 (4)	C17—C18—C19—C20	1.4 (4)
C6—N1—C7—O1	−173.7 (3)	C23—O4—C20—C21	174.2 (3)
C2—N1—C7—C8	−165.4 (3)	C23—O4—C20—C19	−5.0 (4)
C6—N1—C7—C8	8.2 (4)	C18—C19—C20—O4	178.5 (3)
O1—C7—C8—Cl1	69.3 (3)	C18—C19—C20—C21	−0.7 (4)
N1—C7—C8—Cl1	−112.5 (3)	O4—C20—C21—C22	−179.8 (3)
O1—C7—C8—Cl2	−50.9 (3)	C19—C20—C21—C22	−0.6 (4)
N1—C7—C8—Cl2	127.3 (3)	C20—C21—C22—C17	1.2 (4)
N1—C2—C9—C14	−136.5 (3)	C18—C17—C22—C21	−0.5 (4)
C3—C2—C9—C14	−10.6 (5)	C6—C17—C22—C21	176.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.98	2.31	3.264 (4)	164
C8—H8···O1i	0.98	2.52	3.363 (4)	144
C18—H18···O1i	0.93	2.57	3.391 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.98	2.31	3.264 (4)	164
C8—H8⋯O1i	0.98	2.52	3.363 (4)	144
C18—H18⋯O1i	0.93	2.57	3.391 (4)	147

Symmetry code: (i) .