1-Dichloro-acetyl-r-2,c-6-bis-(4-methoxy-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one.

In the title compound, C(23)H(25)Cl(2)NO(4), the piperidine ring adopts a distorted boat conformation. The dihedral angle between the benzene rings is 54.8 (1)°. In the crystal, the mol-ecules are linked into a two-dimensional network parallel to the ab plane by C-H⋯O hydrogen bonds.

Related literature

For the biological properties of piperidin-4-one compounds, see: El-Subbagh et al. (2000 ▶); Jerom & Spencer (1988 ▶); Perumal et al. (2001 ▶); Hagenbach & Gysin (1952 ▶); Mobio et al. (1989 ▶); Katritzky & Fan (1990 ▶); Ganellin & Spickett (1965 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H25Cl2NO4

M = 450.34

Monoclinic,

a = 8.1251 (7) Å

b = 9.9702 (9) Å

c = 27.649 (2) Å

β = 92.265 (5)°

V = 2238.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.27 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.917, T max = 0.929

19833 measured reflections

5379 independent reflections

3699 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.123

S = 1.03

5379 reflections

276 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.36 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/S1600536809054725/ci2992sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054725/ci2992Isup2.hkl

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

C23H25Cl2NO4	F(000) = 944
Mr = 450.34	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2335 reflections
a = 8.1251 (7) Å	θ = 1.5–28.4°
b = 9.9702 (9) Å	µ = 0.32 mm−1
c = 27.649 (2) Å	T = 293 K
β = 92.265 (5)°	Block, colourless
V = 2238.0 (3) Å3	0.27 × 0.26 × 0.23 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5379 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→10
Tmin = 0.917, Tmax = 0.929	k = −13→13
19833 measured reflections	l = −36→36

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.6929P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5379 reflections	Δρmax = 0.27 e Å−3
276 parameters	Δρmin = −0.36 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: 0.0028 (7)

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	0.25916 (8)	1.01921 (6)	0.20873 (3)	0.0839 (2)
Cl2	0.26208 (12)	0.94382 (8)	0.10863 (3)	0.1095 (3)
O1	0.03043 (18)	0.80082 (15)	0.18222 (7)	0.0785 (5)
O2	0.7057 (2)	0.78446 (18)	0.00094 (6)	0.0835 (5)
O3	0.42430 (17)	0.31447 (14)	0.24506 (5)	0.0588 (4)
O4	−0.1564 (2)	0.25273 (19)	0.03205 (6)	0.0880 (5)
N1	0.23306 (16)	0.64601 (13)	0.17753 (5)	0.0373 (3)
C2	0.41000 (18)	0.60777 (16)	0.17209 (6)	0.0347 (3)
H2	0.4747	0.6462	0.1994	0.042*
C3	0.42732 (19)	0.45310 (16)	0.17457 (6)	0.0375 (4)
H3	0.3593	0.4165	0.1476	0.045*
C4	0.3566 (2)	0.40055 (17)	0.22066 (6)	0.0400 (4)
C5	0.1976 (2)	0.46357 (18)	0.23518 (6)	0.0429 (4)
H5	0.1227	0.3916	0.2443	0.051*
C6	0.1163 (2)	0.54088 (17)	0.19306 (6)	0.0407 (4)
H6	0.0221	0.5882	0.2061	0.049*
C7	0.1748 (2)	0.77330 (18)	0.17704 (7)	0.0466 (4)
C8	0.2948 (2)	0.88677 (18)	0.16834 (7)	0.0536 (5)
H8	0.4082	0.8544	0.1731	0.064*
C9	0.48157 (19)	0.65819 (16)	0.12568 (6)	0.0367 (4)
C10	0.4080 (2)	0.63098 (19)	0.08098 (6)	0.0451 (4)
H10	0.3086	0.5846	0.0793	0.054*
C11	0.4787 (2)	0.6711 (2)	0.03850 (7)	0.0530 (5)
H11	0.4274	0.6514	0.0087	0.064*
C12	0.6256 (3)	0.7404 (2)	0.04089 (8)	0.0563 (5)
C13	0.7005 (2)	0.76910 (19)	0.08502 (8)	0.0561 (5)
H13	0.7992	0.8165	0.0866	0.067*
C14	0.6297 (2)	0.72769 (18)	0.12718 (7)	0.0471 (4)
H14	0.6821	0.7467	0.1569	0.056*
C15	0.6402 (4)	0.7474 (3)	−0.04496 (10)	0.1007 (10)
H15A	0.6237	0.6521	−0.0460	0.151*
H15B	0.7155	0.7728	−0.0693	0.151*
H15C	0.5368	0.7921	−0.0510	0.151*
C16	0.6029 (2)	0.4058 (2)	0.16746 (8)	0.0572 (5)
H16A	0.6762	0.4496	0.1905	0.086*
H16B	0.6341	0.4276	0.1353	0.086*
H16C	0.6091	0.3105	0.1721	0.086*
C17	0.2310 (3)	0.5525 (2)	0.27953 (7)	0.0608 (5)
H17A	0.2733	0.4986	0.3060	0.091*
H17B	0.1304	0.5947	0.2884	0.091*
H17C	0.3103	0.6200	0.2721	0.091*
C18	0.04865 (18)	0.45810 (17)	0.15056 (6)	0.0401 (4)
C19	0.0299 (2)	0.32074 (18)	0.15241 (7)	0.0477 (4)
H19	0.0635	0.2754	0.1805	0.057*
C20	−0.0373 (2)	0.2483 (2)	0.11393 (7)	0.0546 (5)
H20	−0.0482	0.1557	0.1162	0.066*
C21	−0.0879 (2)	0.3135 (2)	0.07232 (7)	0.0572 (5)
C22	−0.0711 (2)	0.4514 (2)	0.06939 (7)	0.0582 (5)
H22	−0.1049	0.4963	0.0412	0.070*
C23	−0.0045 (2)	0.5217 (2)	0.10811 (7)	0.0489 (4)
H23	0.0053	0.6144	0.1058	0.059*
C24	−0.1684 (5)	0.1120 (3)	0.03207 (13)	0.1282 (14)
H24A	−0.0602	0.0738	0.0357	0.192*
H24B	−0.2197	0.0825	0.0021	0.192*
H24C	−0.2335	0.0838	0.0584	0.192*

	U11	U22	U33	U12	U13	U23
Cl1	0.0931 (5)	0.0454 (3)	0.1115 (5)	0.0192 (3)	−0.0188 (4)	−0.0273 (3)
Cl2	0.1680 (8)	0.0806 (5)	0.0815 (5)	0.0454 (5)	0.0254 (5)	0.0328 (4)
O1	0.0488 (8)	0.0526 (9)	0.1349 (15)	0.0178 (7)	0.0149 (9)	−0.0099 (9)
O2	0.0905 (12)	0.0833 (12)	0.0795 (11)	−0.0124 (10)	0.0404 (9)	0.0208 (9)
O3	0.0665 (9)	0.0521 (8)	0.0577 (8)	0.0080 (7)	0.0027 (7)	0.0194 (7)
O4	0.0982 (13)	0.0853 (12)	0.0777 (11)	0.0069 (10)	−0.0324 (9)	−0.0231 (9)
N1	0.0331 (7)	0.0329 (7)	0.0461 (7)	0.0036 (6)	0.0056 (6)	−0.0005 (6)
C2	0.0295 (8)	0.0346 (8)	0.0400 (8)	0.0026 (7)	0.0028 (6)	−0.0002 (7)
C3	0.0368 (8)	0.0347 (8)	0.0411 (8)	0.0054 (7)	0.0052 (6)	0.0028 (7)
C4	0.0446 (9)	0.0355 (9)	0.0399 (8)	−0.0032 (8)	−0.0004 (7)	0.0005 (7)
C5	0.0448 (9)	0.0443 (10)	0.0403 (9)	−0.0049 (8)	0.0108 (7)	0.0001 (8)
C6	0.0327 (8)	0.0413 (9)	0.0489 (9)	0.0009 (7)	0.0107 (7)	−0.0014 (8)
C7	0.0437 (10)	0.0386 (9)	0.0574 (10)	0.0089 (8)	0.0025 (8)	−0.0050 (8)
C8	0.0599 (12)	0.0335 (9)	0.0675 (12)	0.0111 (9)	0.0015 (9)	0.0006 (9)
C9	0.0332 (8)	0.0314 (8)	0.0457 (9)	0.0030 (7)	0.0047 (7)	0.0042 (7)
C10	0.0386 (9)	0.0488 (10)	0.0484 (9)	−0.0037 (8)	0.0052 (7)	0.0056 (8)
C11	0.0550 (11)	0.0589 (12)	0.0455 (10)	0.0019 (10)	0.0078 (8)	0.0089 (9)
C12	0.0575 (12)	0.0486 (11)	0.0645 (12)	0.0050 (10)	0.0234 (10)	0.0158 (10)
C13	0.0415 (10)	0.0453 (11)	0.0824 (14)	−0.0057 (9)	0.0143 (10)	0.0102 (10)
C14	0.0397 (9)	0.0403 (9)	0.0612 (11)	−0.0019 (8)	0.0021 (8)	0.0049 (8)
C15	0.132 (3)	0.105 (2)	0.0691 (17)	0.0001 (19)	0.0486 (17)	0.0209 (16)
C16	0.0496 (11)	0.0542 (11)	0.0691 (12)	0.0199 (9)	0.0174 (9)	0.0149 (10)
C17	0.0735 (14)	0.0637 (13)	0.0459 (10)	0.0017 (11)	0.0100 (9)	−0.0107 (9)
C18	0.0269 (8)	0.0437 (9)	0.0500 (9)	0.0019 (7)	0.0051 (7)	0.0009 (8)
C19	0.0434 (10)	0.0448 (10)	0.0549 (10)	0.0009 (8)	−0.0001 (8)	0.0033 (8)
C20	0.0490 (11)	0.0443 (10)	0.0701 (13)	0.0017 (9)	−0.0040 (9)	−0.0066 (10)
C21	0.0456 (11)	0.0642 (13)	0.0613 (12)	0.0067 (10)	−0.0060 (9)	−0.0129 (10)
C22	0.0495 (11)	0.0697 (14)	0.0545 (11)	0.0055 (10)	−0.0087 (9)	0.0068 (10)
C23	0.0390 (9)	0.0470 (10)	0.0606 (11)	0.0019 (8)	0.0002 (8)	0.0063 (9)
C24	0.163 (3)	0.085 (2)	0.131 (3)	0.030 (2)	−0.063 (2)	−0.055 (2)

Cl1—C8	1.7609 (19)	C10—H10	0.93
Cl2—C8	1.757 (2)	C11—C12	1.379 (3)
O1—C7	1.218 (2)	C11—H11	0.93
O2—C12	1.376 (2)	C12—C13	1.372 (3)
O2—C15	1.406 (3)	C13—C14	1.383 (3)
O3—C4	1.210 (2)	C13—H13	0.93
O4—C21	1.367 (2)	C14—H14	0.93
O4—C24	1.406 (4)	C15—H15A	0.96
N1—C7	1.354 (2)	C15—H15B	0.96
N1—C6	1.489 (2)	C15—H15C	0.96
N1—C2	1.501 (2)	C16—H16A	0.96
C2—C9	1.516 (2)	C16—H16B	0.96
C2—C3	1.550 (2)	C16—H16C	0.96
C2—H2	0.98	C17—H17A	0.96
C3—C4	1.512 (2)	C17—H17B	0.96
C3—C16	1.523 (2)	C17—H17C	0.96
C3—H3	0.98	C18—C19	1.379 (2)
C4—C5	1.506 (2)	C18—C23	1.388 (2)
C5—C6	1.525 (2)	C19—C20	1.380 (3)
C5—C17	1.529 (2)	C19—H19	0.93
C5—H5	0.98	C20—C21	1.370 (3)
C6—C18	1.521 (2)	C20—H20	0.93
C6—H6	0.98	C21—C22	1.384 (3)
C7—O1	1.218 (2)	C22—C23	1.373 (3)
C7—C8	1.519 (3)	C22—H22	0.93
C8—H8	0.98	C23—H23	0.93
C9—C10	1.378 (2)	C24—H24A	0.96
C9—C14	1.388 (2)	C24—H24B	0.96
C10—C11	1.386 (2)	C24—H24C	0.96
C12—O2—C15	117.82 (19)	C13—C12—C11	119.99 (17)
C21—O4—C24	117.9 (2)	O2—C12—C11	123.9 (2)
C7—N1—C6	115.85 (14)	C12—C13—C14	120.19 (18)
C7—N1—C2	124.96 (14)	C12—C13—H13	119.9
C6—N1—C2	118.31 (12)	C14—C13—H13	119.9
N1—C2—C9	113.69 (12)	C13—C14—C9	120.84 (18)
N1—C2—C3	109.51 (12)	C13—C14—H14	119.6
C9—C2—C3	109.29 (13)	C9—C14—H14	119.6
N1—C2—H2	108.1	O2—C15—H15A	109.5
C9—C2—H2	108.1	O2—C15—H15B	109.5
C3—C2—H2	108.1	H15A—C15—H15B	109.5
C4—C3—C16	113.00 (14)	O2—C15—H15C	109.5
C4—C3—C2	110.20 (13)	H15A—C15—H15C	109.5
C16—C3—C2	112.72 (14)	H15B—C15—H15C	109.5
C4—C3—H3	106.8	C3—C16—H16A	109.5
C16—C3—H3	106.8	C3—C16—H16B	109.5
C2—C3—H3	106.8	H16A—C16—H16B	109.5
O3—C4—C5	121.55 (15)	C3—C16—H16C	109.5
O3—C4—C3	122.41 (16)	H16A—C16—H16C	109.5
C5—C4—C3	116.02 (14)	H16B—C16—H16C	109.5
C4—C5—C6	110.96 (13)	C5—C17—H17A	109.5
C4—C5—C17	109.19 (14)	C5—C17—H17B	109.5
C6—C5—C17	112.17 (15)	H17A—C17—H17B	109.5
C4—C5—H5	108.1	C5—C17—H17C	109.5
C6—C5—H5	108.1	H17A—C17—H17C	109.5
C17—C5—H5	108.1	H17B—C17—H17C	109.5
N1—C6—C18	111.99 (13)	C19—C18—C23	116.98 (17)
N1—C6—C5	108.31 (13)	C19—C18—C6	123.20 (16)
C18—C6—C5	116.62 (14)	C23—C18—C6	119.76 (16)
N1—C6—H6	106.4	C18—C19—C20	122.15 (18)
C18—C6—H6	106.4	C18—C19—H19	118.9
C5—C6—H6	106.4	C20—C19—H19	118.9
O1—C7—N1	123.20 (17)	C21—C20—C19	119.69 (19)
O1—C7—C8	118.56 (16)	C21—C20—H20	120.2
N1—C7—C8	118.22 (15)	C19—C20—H20	120.2
C7—C8—Cl2	108.39 (14)	O4—C21—C20	125.0 (2)
C7—C8—Cl1	109.58 (13)	O4—C21—C22	115.48 (19)
Cl2—C8—Cl1	109.31 (10)	C20—C21—C22	119.56 (19)
C7—C8—H8	109.8	C23—C22—C21	119.88 (19)
Cl2—C8—H8	109.8	C23—C22—H22	120.1
Cl1—C8—H8	109.8	C21—C22—H22	120.1
C10—C9—C14	118.03 (16)	C22—C23—C18	121.74 (18)
C10—C9—C2	121.78 (14)	C22—C23—H23	119.1
C14—C9—C2	120.10 (15)	C18—C23—H23	119.1
C9—C10—C11	121.56 (17)	O4—C24—H24A	109.5
C9—C10—H10	119.2	O4—C24—H24B	109.5
C11—C10—H10	119.2	H24A—C24—H24B	109.5
C12—C11—C10	119.40 (18)	O4—C24—H24C	109.5
C12—C11—H11	120.3	H24A—C24—H24C	109.5
C10—C11—H11	120.3	H24B—C24—H24C	109.5
C13—C12—O2	116.11 (19)
C7—N1—C2—C9	−57.4 (2)	N1—C2—C9—C10	−54.2 (2)
C6—N1—C2—C9	133.76 (14)	C3—C2—C9—C10	68.44 (19)
C7—N1—C2—C3	179.99 (15)	N1—C2—C9—C14	129.30 (15)
C6—N1—C2—C3	11.19 (18)	C3—C2—C9—C14	−108.02 (17)
N1—C2—C3—C4	−54.86 (17)	C14—C9—C10—C11	0.1 (3)
C9—C2—C3—C4	180.00 (13)	C2—C9—C10—C11	−176.45 (16)
N1—C2—C3—C16	177.88 (14)	C9—C10—C11—C12	−0.3 (3)
C9—C2—C3—C16	52.74 (18)	C15—O2—C12—C13	174.8 (2)
C16—C3—C4—O3	−10.3 (2)	C15—O2—C12—C11	−5.1 (3)
C2—C3—C4—O3	−137.45 (17)	C10—C11—C12—C13	0.0 (3)
C16—C3—C4—C5	168.53 (15)	C10—C11—C12—O2	179.92 (19)
C2—C3—C4—C5	41.42 (19)	O2—C12—C13—C14	−179.40 (18)
O3—C4—C5—C6	−165.48 (16)	C11—C12—C13—C14	0.5 (3)
C3—C4—C5—C6	15.6 (2)	C12—C13—C14—C9	−0.8 (3)
O3—C4—C5—C17	70.4 (2)	C10—C9—C14—C13	0.5 (3)
C3—C4—C5—C17	−108.51 (17)	C2—C9—C14—C13	177.04 (16)
C7—N1—C6—C18	105.44 (17)	N1—C6—C18—C19	138.12 (16)
C2—N1—C6—C18	−84.76 (17)	C5—C6—C18—C19	12.6 (2)
C7—N1—C6—C5	−124.58 (15)	N1—C6—C18—C23	−44.8 (2)
C2—N1—C6—C5	45.23 (18)	C5—C6—C18—C23	−170.39 (14)
C4—C5—C6—N1	−58.81 (17)	C23—C18—C19—C20	0.5 (3)
C17—C5—C6—N1	63.61 (17)	C6—C18—C19—C20	177.62 (16)
C4—C5—C6—C18	68.56 (18)	C18—C19—C20—C21	−0.1 (3)
C17—C5—C6—C18	−169.01 (14)	C24—O4—C21—C20	−3.5 (4)
C6—N1—C7—O1	−9.9 (3)	C24—O4—C21—C22	176.7 (3)
C2—N1—C7—O1	−178.98 (17)	C19—C20—C21—O4	−179.80 (19)
C6—N1—C7—C8	171.65 (15)	C19—C20—C21—C22	−0.1 (3)
C2—N1—C7—C8	2.6 (2)	O4—C21—C22—C23	179.61 (18)
O1—C7—C8—Cl2	−74.4 (2)	C20—C21—C22—C23	−0.1 (3)
N1—C7—C8—Cl2	104.09 (17)	C21—C22—C23—C18	0.6 (3)
O1—C7—C8—Cl1	44.8 (2)	C19—C18—C23—C22	−0.7 (3)
N1—C7—C8—Cl1	−136.69 (15)	C6—C18—C23—C22	−177.94 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.98	2.40	3.326 (2)	158
C5—H5···O1ii	0.98	2.59	3.408 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.98	2.40	3.326 (2)	158
C5—H5⋯O1ii	0.98	2.59	3.408 (2)	141

Symmetry codes: (i) ; (ii) .