1-Dichloro­acetyl-r-2,c-6-bis­(4-methoxy­phen­yl)-t-3,t-5-dimethyl­piperidin-4-one

Ravichandran, K.; Ramesh, P.; Neeladevi, C.; Ponnuswamy, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536809054725

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o263

https://doi.org/10.1107/S1600536809054725

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1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one

K. Ravichandran,^a P. Ramesh,^a C. Neeladevi,^b S. Ponnuswamy ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 December 2009; accepted 19 December 2009; online 9 January 2010)

In the title compound, C₂₃H₂₅Cl₂NO₄, the piperidine ring adopts a distorted boat conformation. The dihedral angle between the benzene rings is 54.8 (1)°. In the crystal, the molecules 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_r = 450.34
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.123
S = 1.03
5379 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809054725/ci2992sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054725/ci2992Isup2.hkl

checkCIF report

Comment top

Piperidin-4-one derivatives possess varied biological properties such as antiviral, antitumour (El-Subbagh et al., 2000), analgesic (Jerom & Spencer, 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), antimicrobial, bactericidal, fungicidal, herbicidal, insecticidal, antihistaminic, anti-inflammatory, anticancer, CNS stimulant and depressant activities (Mobio et al., 1989; Katritzky & Fan, 1990; Ganellin & Spickett, 1965). In view of these importance and to ascertain the molecular conformation, a crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. The piperidine ring adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q₂ = 0.737 (2) Å, q₃ = 0.013 (2) Å, φ₂ = 285.4 (1)° and Δ_s(C3 or C6) = 19.0 (2)°. The sum of the bond angles around the atom N1 (359.1°) of the piperidine ring is in accordance with sp² hybridization.

The crystal packing is stabilized by C—H···O intermolecular interactions. Atom C2 of the molecule at (x, y, z) donates a proton to atom O3 of the molecule at (1 - x, 1/2 + y, 1/2 - z), forming a C5 (Bernstein et al., 1995) zigzag chain running along the b axis. The chains are cross linked via C5—H5···O1 intermolecular interactions, forming a two-dimensional network parallel to the ab plane.

Related literature top

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 top

To a solution of r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one (1.69 g) in anhydrous benzene (60 ml) was added triethylamine (2.08 ml) and dichloroacetylchloride (1.42 ml). The reaction mixture was allowed to stir at room temperature for 8 hr and the solution was washed with water (4 × 25 ml). The organic layer was dried over anhydrous sodium sulfate, passed through a short column of silica, evaporated and crystallized from benzene-petroleum ether (60–80° C) (9:1 v/v).

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)- t-3,t-5-dimethylpiperidin-4-one top

Crystal data top

C₂₃H₂₅Cl₂NO₄	F(000) = 944
M_r = 450.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0497P)² + 0.6929P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5379 reflections	Δρ_max = 0.27 e Å⁻³
276 parameters	Δρ_min = −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)

Crystal data top

C₂₃H₂₅Cl₂NO₄	V = 2238.0 (3) Å³
M_r = 450.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1251 (7) Å	µ = 0.32 mm⁻¹
b = 9.9702 (9) Å	T = 293 K
c = 27.649 (2) Å	0.27 × 0.26 × 0.23 mm
β = 92.265 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5379 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3699 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.929	R_int = 0.026
19833 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
5379 reflections	Δρ_min = −0.36 e Å⁻³
276 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅Cl₂NO₄
M_r	450.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1251 (7), 9.9702 (9), 27.649 (2)
β (°)	92.265 (5)
V (Å³)	2238.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.27 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.917, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	19833, 5379, 3699
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.03
No. of reflections	5379
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar's College, Velur, Namakkal, Tamil Nadu, India, for the encouragement to pursue the programme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-obaid, A. M. (2000). J. Med. Chem. 43, 2915–2921. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ganellin, C. R. & Spickett, R. G. W. (1965). J. Med. Chem. 8, 619–625. CrossRef CAS PubMed Web of Science Google Scholar
Hagenbach, R. E. & Gysin, H. (1952). Experientia, 8, 184–185. CrossRef PubMed CAS Web of Science Google Scholar
Jerom, B. R. & Spencer, K. H. (1988). Eur. Patent Appl. EP 277794. Google Scholar
Katritzky, A. R. & Fan, W. J. (1990). J. Org. Chem. 55, 3205–3209. CrossRef CAS Web of Science Google Scholar
Mobio, I. G., Soldatenkov, A. T., Federov, V. O., Ageev, E. A., Sergeeva, N. D., Lin, S., Stashenku, E. E., Prostakov, N. S. & Andreeva, E. L. (1989). Khim. Farm. Zh. 23, 421–427. CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Perumal, R. V., Adiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156–159. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Di­chloro­acetyl-r-2,c-6-bis­­(4-meth­oxy­phen­yl)-t-3,t-5-di­methyl­piperidin-4-one

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Experimental

Crystal data

Data collection

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Supporting information

Acknowledgements

References

organic compounds

1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one