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

In the title compound, C(23)H(26)ClNO(4), the piperidine ring adopts a distorted boat conformation. The two methoxy-phenyl groups at the 2 and 6 positions of the piperidine ring are in axial and equatorial orientations. An intra-molecular C-H⋯Cl inter-action is observed. In the crystal, the mol-ecules are linked into zigzag chains along the b axis by C-H⋯π inter-molecular inter-actions.

Related literature

For general background to piperidine derivatives, see: Bochringer & Soehne (1961 ▶); Ganellin & Spickett (1965 ▶); Mobio et al. (1990 ▶); Severs et al. (1965 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C23H26ClNO4

M = 415.90

Monoclinic,

a = 12.5928 (4) Å

b = 9.4141 (3) Å

c = 17.9070 (6) Å

β = 90.826 (1)°

V = 2122.65 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.18 × 0.17 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.967, T max = 0.971

28132 measured reflections

6666 independent reflections

4339 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.143

S = 1.01

6666 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.47 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: 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/S1600536809041555/ci2910sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041555/ci2910Isup2.hkl

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

C23H26ClNO4	F(000) = 880
Mr = 415.90	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6666 reflections
a = 12.5928 (4) Å	θ = 1.6–30.9°
b = 9.4141 (3) Å	µ = 0.21 mm−1
c = 17.9070 (6) Å	T = 293 K
β = 90.826 (1)°	Block, colourless
V = 2122.65 (12) Å3	0.18 × 0.17 × 0.16 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	6666 independent reflections
Radiation source: fine-focus sealed tube	4339 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 30.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −18→18
Tmin = 0.967, Tmax = 0.971	k = −8→13
28132 measured reflections	l = −25→25

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) = 0.143	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.6368P] where P = (Fo2 + 2Fc2)/3
6666 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C2	0.67796 (11)	0.51678 (14)	0.45686 (8)	0.0334 (3)
H2	0.6125	0.5248	0.4855	0.040*
C3	0.75746 (12)	0.62207 (15)	0.49301 (8)	0.0384 (3)
C4	0.86517 (12)	0.60541 (15)	0.45768 (8)	0.0379 (3)
C5	0.88574 (11)	0.46526 (15)	0.41983 (9)	0.0365 (3)
H5A	0.9617	0.4478	0.4211	0.044*
H5B	0.8642	0.4736	0.3678	0.044*
C6	0.82990 (10)	0.33570 (14)	0.45296 (8)	0.0311 (3)
H6	0.8660	0.3114	0.5001	0.037*
C7	0.65532 (12)	0.27982 (16)	0.50811 (8)	0.0383 (3)
C8	0.70342 (13)	0.14302 (16)	0.53726 (9)	0.0449 (4)
H8A	0.7515	0.1044	0.5006	0.054*
H8B	0.6476	0.0739	0.5454	0.054*
C9	0.64596 (11)	0.53902 (15)	0.37535 (8)	0.0349 (3)
C10	0.69598 (13)	0.62843 (17)	0.32557 (9)	0.0437 (4)
H10	0.7534	0.6826	0.3420	0.052*
C11	0.66241 (14)	0.63895 (19)	0.25190 (10)	0.0510 (4)
H11	0.6971	0.7000	0.2195	0.061*
C12	0.57764 (14)	0.5591 (2)	0.22634 (9)	0.0480 (4)
C13	0.52617 (13)	0.4698 (2)	0.27464 (10)	0.0512 (4)
H13	0.4689	0.4156	0.2579	0.061*
C14	0.56023 (12)	0.46113 (18)	0.34841 (9)	0.0439 (4)
H14	0.5245	0.4012	0.3808	0.053*
C15	0.46636 (16)	0.4921 (3)	0.12384 (11)	0.0795 (7)
H15A	0.4826	0.3933	0.1310	0.119*
H15B	0.4566	0.5109	0.0715	0.119*
H15C	0.4024	0.5152	0.1497	0.119*
C16	0.71693 (16)	0.77524 (17)	0.48942 (11)	0.0560 (5)
H16A	0.7669	0.8368	0.5142	0.084*
H16B	0.6495	0.7813	0.5136	0.084*
H16C	0.7089	0.8037	0.4382	0.084*
C17	0.77419 (16)	0.5830 (2)	0.57605 (9)	0.0532 (4)
H17A	0.8068	0.4911	0.5797	0.080*
H17B	0.7068	0.5813	0.6004	0.080*
H17C	0.8193	0.6524	0.5996	0.080*
C18	0.84238 (11)	0.21143 (14)	0.39983 (8)	0.0316 (3)
C19	0.92043 (12)	0.11115 (16)	0.41388 (8)	0.0375 (3)
H19	0.9628	0.1196	0.4566	0.045*
C20	0.93692 (12)	−0.00147 (16)	0.36576 (9)	0.0398 (3)
H20	0.9899	−0.0677	0.3760	0.048*
C21	0.87401 (12)	−0.01445 (16)	0.30252 (8)	0.0396 (3)
C22	0.79620 (12)	0.08571 (18)	0.28752 (9)	0.0426 (3)
H22	0.7540	0.0773	0.2447	0.051*
C23	0.78075 (11)	0.19756 (16)	0.33546 (8)	0.0383 (3)
H23	0.7285	0.2646	0.3246	0.046*
C24	0.96836 (19)	−0.2174 (2)	0.25982 (12)	0.0725 (6)
H24A	1.0340	−0.1657	0.2586	0.109*
H24B	0.9664	−0.2851	0.2198	0.109*
H24C	0.9630	−0.2662	0.3067	0.109*
Cl1	0.77329 (5)	0.17452 (7)	0.62195 (3)	0.0835 (2)
N1	0.71792 (9)	0.36987 (12)	0.46958 (6)	0.0315 (2)
O1	0.56230 (9)	0.30440 (14)	0.52104 (8)	0.0578 (3)
O2	0.55150 (11)	0.57620 (17)	0.15243 (7)	0.0681 (4)
O3	0.93212 (10)	0.69712 (12)	0.45950 (7)	0.0550 (3)
O4	0.88237 (11)	−0.12170 (14)	0.25156 (7)	0.0596 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0350 (7)	0.0274 (7)	0.0379 (7)	0.0050 (5)	0.0009 (5)	−0.0015 (5)
C3	0.0464 (8)	0.0270 (7)	0.0417 (8)	0.0035 (6)	−0.0056 (6)	−0.0044 (6)
C4	0.0418 (8)	0.0291 (7)	0.0423 (8)	−0.0017 (6)	−0.0119 (6)	0.0027 (6)
C5	0.0327 (7)	0.0304 (7)	0.0465 (8)	−0.0016 (5)	0.0016 (6)	0.0003 (6)
C6	0.0308 (6)	0.0267 (6)	0.0357 (7)	0.0028 (5)	−0.0001 (5)	−0.0001 (5)
C7	0.0402 (8)	0.0332 (7)	0.0416 (8)	−0.0004 (6)	0.0064 (6)	−0.0003 (6)
C8	0.0522 (9)	0.0340 (8)	0.0487 (9)	−0.0010 (7)	0.0108 (7)	0.0069 (7)
C9	0.0337 (7)	0.0306 (7)	0.0403 (7)	0.0056 (5)	−0.0024 (6)	−0.0017 (6)
C10	0.0457 (9)	0.0375 (8)	0.0477 (9)	−0.0046 (7)	−0.0070 (7)	0.0052 (7)
C11	0.0558 (10)	0.0503 (10)	0.0469 (9)	−0.0004 (8)	−0.0009 (7)	0.0113 (7)
C12	0.0490 (9)	0.0542 (10)	0.0404 (8)	0.0116 (8)	−0.0067 (7)	−0.0022 (7)
C13	0.0422 (9)	0.0585 (11)	0.0526 (10)	−0.0019 (8)	−0.0102 (7)	−0.0074 (8)
C14	0.0379 (8)	0.0472 (9)	0.0465 (9)	−0.0026 (7)	−0.0017 (6)	0.0023 (7)
C15	0.0526 (11)	0.136 (2)	0.0490 (11)	0.0212 (13)	−0.0153 (9)	−0.0217 (12)
C16	0.0656 (11)	0.0311 (8)	0.0710 (12)	0.0096 (8)	−0.0080 (9)	−0.0120 (8)
C17	0.0717 (12)	0.0488 (10)	0.0389 (8)	0.0001 (9)	−0.0053 (8)	−0.0079 (7)
C18	0.0323 (7)	0.0264 (6)	0.0361 (7)	−0.0001 (5)	0.0051 (5)	0.0008 (5)
C19	0.0417 (8)	0.0329 (7)	0.0379 (7)	0.0053 (6)	−0.0003 (6)	0.0012 (6)
C20	0.0442 (8)	0.0311 (7)	0.0444 (8)	0.0096 (6)	0.0068 (6)	0.0012 (6)
C21	0.0458 (8)	0.0329 (7)	0.0403 (8)	−0.0009 (6)	0.0113 (6)	−0.0060 (6)
C22	0.0423 (8)	0.0461 (9)	0.0395 (8)	0.0011 (7)	−0.0011 (6)	−0.0084 (7)
C23	0.0351 (7)	0.0376 (8)	0.0422 (8)	0.0055 (6)	−0.0010 (6)	−0.0029 (6)
C24	0.0957 (16)	0.0581 (12)	0.0642 (13)	0.0275 (11)	0.0172 (11)	−0.0180 (10)
Cl1	0.1001 (5)	0.0783 (4)	0.0713 (4)	−0.0053 (3)	−0.0267 (3)	0.0256 (3)
N1	0.0323 (6)	0.0261 (5)	0.0361 (6)	0.0023 (4)	0.0033 (4)	−0.0003 (4)
O1	0.0417 (6)	0.0531 (8)	0.0791 (9)	0.0033 (5)	0.0185 (6)	0.0133 (6)
O2	0.0717 (9)	0.0898 (11)	0.0424 (7)	0.0092 (8)	−0.0137 (6)	0.0000 (7)
O3	0.0534 (7)	0.0374 (6)	0.0738 (8)	−0.0140 (5)	−0.0131 (6)	−0.0006 (6)
O4	0.0735 (9)	0.0494 (7)	0.0559 (7)	0.0119 (6)	0.0033 (6)	−0.0223 (6)

C2—N1	1.4881 (17)	C13—C14	1.385 (2)
C2—C9	1.5231 (19)	C13—H13	0.93
C2—C3	1.544 (2)	C14—H14	0.93
C2—H2	0.98	C15—O2	1.422 (3)
C3—C4	1.513 (2)	C15—H15A	0.96
C3—C16	1.531 (2)	C15—H15B	0.96
C3—C17	1.543 (2)	C15—H15C	0.96
C4—O3	1.2068 (18)	C16—H16A	0.96
C4—C5	1.507 (2)	C16—H16B	0.96
C5—C6	1.5317 (19)	C16—H16C	0.96
C5—H5A	0.97	C17—H17A	0.96
C5—H5B	0.97	C17—H17B	0.96
C6—N1	1.4808 (17)	C17—H17C	0.96
C6—C18	1.5174 (19)	C18—C19	1.3832 (19)
C6—H6	0.98	C18—C23	1.386 (2)
C7—O1	1.2195 (18)	C19—C20	1.384 (2)
C7—N1	1.3534 (18)	C19—H19	0.93
C7—C8	1.513 (2)	C20—C21	1.378 (2)
C8—Cl1	1.7672 (18)	C20—H20	0.93
C8—H8A	0.97	C21—O4	1.3659 (18)
C8—H8B	0.97	C21—C22	1.383 (2)
C9—C10	1.384 (2)	C22—C23	1.374 (2)
C9—C14	1.386 (2)	C22—H22	0.93
C10—C11	1.383 (2)	C23—H23	0.93
C10—H10	0.93	C24—O4	1.414 (2)
C11—C12	1.378 (2)	C24—H24A	0.96
C11—H11	0.93	C24—H24B	0.96
C12—O2	1.3688 (19)	C24—H24C	0.96
C12—C13	1.375 (3)
N1—C2—C9	111.02 (11)	C13—C14—C9	121.97 (16)
N1—C2—C3	108.46 (11)	C13—C14—H14	119.0
C9—C2—C3	118.32 (12)	C9—C14—H14	119.0
N1—C2—H2	106.1	O2—C15—H15A	109.5
C9—C2—H2	106.1	O2—C15—H15B	109.5
C3—C2—H2	106.1	H15A—C15—H15B	109.5
C4—C3—C16	112.36 (14)	O2—C15—H15C	109.5
C4—C3—C17	105.51 (12)	H15A—C15—H15C	109.5
C16—C3—C17	107.79 (13)	H15B—C15—H15C	109.5
C4—C3—C2	109.75 (11)	C3—C16—H16A	109.5
C16—C3—C2	111.92 (12)	C3—C16—H16B	109.5
C17—C3—C2	109.24 (13)	H16A—C16—H16B	109.5
O3—C4—C5	120.92 (15)	C3—C16—H16C	109.5
O3—C4—C3	123.00 (14)	H16A—C16—H16C	109.5
C5—C4—C3	116.08 (12)	H16B—C16—H16C	109.5
C4—C5—C6	116.10 (12)	C3—C17—H17A	109.5
C4—C5—H5A	108.3	C3—C17—H17B	109.5
C6—C5—H5A	108.3	H17A—C17—H17B	109.5
C4—C5—H5B	108.3	C3—C17—H17C	109.5
C6—C5—H5B	108.3	H17A—C17—H17C	109.5
H5A—C5—H5B	107.4	H17B—C17—H17C	109.5
N1—C6—C18	113.65 (11)	C19—C18—C23	118.34 (13)
N1—C6—C5	110.41 (11)	C19—C18—C6	119.47 (12)
C18—C6—C5	108.59 (11)	C23—C18—C6	122.14 (12)
N1—C6—H6	108.0	C18—C19—C20	121.49 (14)
C18—C6—H6	108.0	C18—C19—H19	119.3
C5—C6—H6	108.0	C20—C19—H19	119.3
O1—C7—N1	123.10 (14)	C21—C20—C19	119.34 (13)
O1—C7—C8	118.48 (14)	C21—C20—H20	120.3
N1—C7—C8	118.41 (13)	C19—C20—H20	120.3
C7—C8—Cl1	110.19 (11)	O4—C21—C20	124.44 (14)
C7—C8—H8A	109.6	O4—C21—C22	115.81 (14)
Cl1—C8—H8A	109.6	C20—C21—C22	119.75 (13)
C7—C8—H8B	109.6	C23—C22—C21	120.48 (14)
Cl1—C8—H8B	109.6	C23—C22—H22	119.8
H8A—C8—H8B	108.1	C21—C22—H22	119.8
C10—C9—C14	117.19 (14)	C22—C23—C18	120.59 (14)
C10—C9—C2	125.75 (13)	C22—C23—H23	119.7
C14—C9—C2	117.05 (13)	C18—C23—H23	119.7
C11—C10—C9	121.48 (15)	O4—C24—H24A	109.5
C11—C10—H10	119.3	O4—C24—H24B	109.5
C9—C10—H10	119.3	H24A—C24—H24B	109.5
C12—C11—C10	120.16 (16)	O4—C24—H24C	109.5
C12—C11—H11	119.9	H24A—C24—H24C	109.5
C10—C11—H11	119.9	H24B—C24—H24C	109.5
O2—C12—C13	124.82 (16)	C7—N1—C6	121.99 (11)
O2—C12—C11	115.56 (17)	C7—N1—C2	117.51 (11)
C13—C12—C11	119.62 (15)	C6—N1—C2	119.47 (11)
C12—C13—C14	119.57 (16)	C12—O2—C15	116.88 (17)
C12—C13—H13	120.2	C21—O4—C24	117.84 (15)
C14—C13—H13	120.2
N1—C2—C3—C4	60.28 (14)	C2—C9—C14—C13	−178.09 (14)
C9—C2—C3—C4	−67.26 (15)	N1—C6—C18—C19	−137.78 (13)
N1—C2—C3—C16	−174.25 (13)	C5—C6—C18—C19	98.93 (15)
C9—C2—C3—C16	58.21 (18)	N1—C6—C18—C23	44.94 (18)
N1—C2—C3—C17	−54.95 (16)	C5—C6—C18—C23	−78.35 (16)
C9—C2—C3—C17	177.50 (12)	C23—C18—C19—C20	−0.6 (2)
C16—C3—C4—O3	33.4 (2)	C6—C18—C19—C20	−177.94 (13)
C17—C3—C4—O3	−83.83 (17)	C18—C19—C20—C21	−0.2 (2)
C2—C3—C4—O3	158.58 (14)	C19—C20—C21—O4	−179.33 (14)
C16—C3—C4—C5	−147.13 (13)	C19—C20—C21—C22	0.7 (2)
C17—C3—C4—C5	95.66 (15)	O4—C21—C22—C23	179.63 (14)
C2—C3—C4—C5	−21.92 (16)	C20—C21—C22—C23	−0.4 (2)
O3—C4—C5—C6	148.60 (14)	C21—C22—C23—C18	−0.4 (2)
C3—C4—C5—C6	−30.90 (17)	C19—C18—C23—C22	0.9 (2)
C4—C5—C6—N1	44.12 (16)	C6—C18—C23—C22	178.18 (14)
C4—C5—C6—C18	169.34 (12)	O1—C7—N1—C6	−178.38 (14)
O1—C7—C8—Cl1	−97.54 (16)	C8—C7—N1—C6	2.4 (2)
N1—C7—C8—Cl1	81.75 (15)	O1—C7—N1—C2	13.2 (2)
N1—C2—C9—C10	−113.18 (16)	C8—C7—N1—C2	−166.01 (12)
C3—C2—C9—C10	13.1 (2)	C18—C6—N1—C7	66.53 (17)
N1—C2—C9—C14	65.74 (16)	C5—C6—N1—C7	−171.18 (12)
C3—C2—C9—C14	−167.94 (13)	C18—C6—N1—C2	−125.32 (13)
C14—C9—C10—C11	−0.5 (2)	C5—C6—N1—C2	−3.03 (16)
C2—C9—C10—C11	178.46 (15)	C9—C2—N1—C7	−108.37 (14)
C9—C10—C11—C12	−0.2 (3)	C3—C2—N1—C7	120.03 (14)
C10—C11—C12—O2	−179.32 (16)	C9—C2—N1—C6	82.95 (14)
C10—C11—C12—C13	0.5 (3)	C3—C2—N1—C6	−48.65 (16)
O2—C12—C13—C14	179.75 (16)	C13—C12—O2—C15	−1.6 (3)
C11—C12—C13—C14	0.0 (3)	C11—C12—O2—C15	178.17 (17)
C12—C13—C14—C9	−0.7 (3)	C20—C21—O4—C24	−7.1 (2)
C10—C9—C14—C13	0.9 (2)	C22—C21—O4—C24	172.90 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1	0.98	2.80	3.4684 (15)	126
C24—H24B···Cg1i	0.96	2.78	3.438 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cl1	0.98	2.80	3.4684 (15)	126
C24—H24B⋯Cg1i	0.96	2.78	3.438 (2)	126

Symmetry code: (i) . Cg1 is the centroid of the C18–C23 ring.