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

Thenmozhi, M.; Ponnuswamy, S.; Mohanraj, V.; Vijayalakshmi, R.; Ponnuswamy, M.N.

doi:10.1107/S1600536808040063

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o11

doi:10.1107/S1600536808040063

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

M. Thenmozhi,^a S. Ponnuswamy,^b V. Mohanraj,^b R. Vijayalakshmi ^c and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India, and ^cDepartment of Chemistry, Queen Mary's College (Autonomous), Chennai 600 004, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 15 November 2008; accepted 27 November 2008; online 3 December 2008)

In the title compound, C₂₃H₂₅Cl₂NO₄, the piperidine ring adopts a distorted boat conformation. Inversion-related molecules are linked into centrosymmetric R₂²(16) dimers by paired C—H⋯O hydrogen bonds, and the dimers are connected via C—H⋯O hydrogen bonds into a chain running along [101].

Related literature

For general background, see: Eller et al.(2002 ); Ribeiro da Silva et al. (2007 ). For hybridization, see: Beddoes et al. (1986 ) For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₃H₂₅Cl₂NO₄
M_r = 450.34
Monoclinic, C 2/c
a = 23.6295 (9) Å
b = 10.3999 (4) Å
c = 19.2617 (9) Å
β = 107.734 (1)°
V = 4508.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.911, T_max = 0.939
29354 measured reflections
6905 independent reflections
4138 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.184
S = 1.00
6905 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.98	2.30	3.216 (2)	155
C13—H13⋯O3ⁱⁱ	0.93	2.58	3.453 (3)	155
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040063/ci2726sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040063/ci2726Isup2.hkl

checkCIF report

Comment top

The piperidine compounds are used in chemical industry for the synthesis of pharmacological drugs, either as reactants, solvents or being units of molecular chemical structure of the final compounds. These compounds have significant biological importance with more environmental impact (Ribeiro da Silva et al., 2007). A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as a rubber vulcanization accelerator (Eller et al., 2002).

The piperidine ring adopts a distorted boat conformation, with puckering parameters (Cremer & Pople, 1975) q₂ = 0.606 (2) Å, q₃ = 0.127 (2) Å, and ϕ = 77.5 (2)°, and asymmetry parameter Δ_s(C2) = 18.26 (17)° (Nardelli, 1983). The torsion angles C13—C12—O2—C15 [2.6 (3)°] and C20—C21—O4—C24 [-11.7 (3)°] indicate that the methoxy groups are almost coplanar with the attached rings (Fig.1). The sum of the bond angles around atom N1 (359.4°) of the piperidine ring is in accordance with sp² hybridization (Beddoes et al., 1986). The best plane through the piperidine ring (N1/C3/C4/C6) and methoxyphenyl ring (C9—C14) are orthogonal to one another, with a dihedral angle of 87.18 (7)°, whereas, the other methoxyphenyl ring (C18—C23) is oriented at an angle of 54.47 (7)°.

The molecules at positions (x, y, z) and (1 - x, 1 - y, 1 - z) are linked through a pair of C13—H13···O3 hydrogen bonds forming a cyclic centrosymmetric R₂²(16) dimer (Bernstein et al., 1995). The dimers are linked by intermolecular C6—H6···O1 hydrogen bonds (Table 1) into a chain running along the [101] (Fig.2).

Related literature top

For general background, see: Eller et al.(2002); Ribeiro da Silva et al. (2007). For hybridization, see: Beddoes et al. (1986) For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To the solution of r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one (2 g) in benzene (25 ml), triethylamine (2.0 ml) and dichloroacetyl chloride (1.40 ml) were added and allowed to reflux on a water bath for 5 h. The course of the reaction was monitored by TLC. The solution was concentrated and the resulting mass was crystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the molecules viewed down b axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₃H₂₅Cl₂NO₄	F(000) = 1888
M_r = 450.34	D_x = 1.327 Mg m⁻³
Monoclinic, C2/c	Melting point = 377–379 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.6295 (9) Å	Cell parameters from 6905 reflections
b = 10.3999 (4) Å	θ = 2.2–30.6°
c = 19.2617 (9) Å	µ = 0.32 mm⁻¹
β = 107.734 (1)°	T = 293 K
V = 4508.5 (3) Å³	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6905 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 30.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −32→33
T_min = 0.911, T_max = 0.939	k = −14→14
29354 measured reflections	l = −27→27

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0869P)² + 2.9239P] where P = (F_o² + 2F_c²)/3
6905 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₂₃H₂₅Cl₂NO₄	V = 4508.5 (3) Å³
M_r = 450.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.6295 (9) Å	µ = 0.32 mm⁻¹
b = 10.3999 (4) Å	T = 293 K
c = 19.2617 (9) Å	0.30 × 0.25 × 0.20 mm
β = 107.734 (1)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6905 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4138 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.939	R_int = 0.031
29354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.01	Δρ_max = 0.60 e Å⁻³
6905 reflections	Δρ_min = −0.63 e Å⁻³
275 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	0.18029 (3)	0.52254 (7)	0.14172 (4)	0.0790 (2)
Cl2	0.26274 (4)	0.62339 (11)	0.07261 (4)	0.1127 (4)
O1	0.26407 (7)	0.74756 (16)	0.21261 (9)	0.0635 (4)
O2	0.56012 (6)	0.89254 (16)	0.36906 (9)	0.0604 (4)
O3	0.37036 (9)	0.4204 (2)	0.48165 (10)	0.0798 (6)
O4	0.48349 (7)	0.30777 (15)	0.10880 (9)	0.0592 (4)
N1	0.31916 (6)	0.58476 (15)	0.27717 (8)	0.0402 (3)
C2	0.33601 (8)	0.66580 (19)	0.34377 (10)	0.0407 (4)
H2	0.3092	0.7400	0.3325	0.049*
C3	0.32172 (8)	0.5947 (2)	0.40675 (11)	0.0481 (5)
C4	0.35641 (9)	0.4707 (2)	0.42265 (12)	0.0530 (5)
C5	0.37393 (9)	0.4121 (2)	0.36076 (12)	0.0521 (5)
H5A	0.3721	0.3194	0.3651	0.063*
H5B	0.4151	0.4343	0.3676	0.063*
C6	0.33818 (8)	0.44832 (19)	0.28249 (11)	0.0435 (4)
H6	0.3023	0.3950	0.2685	0.052*
C7	0.28061 (8)	0.6362 (2)	0.21725 (11)	0.0460 (4)
C8	0.25568 (9)	0.5486 (2)	0.15090 (12)	0.0550 (5)
H8	0.2771	0.4665	0.1587	0.066*
C9	0.39837 (8)	0.72041 (18)	0.35651 (10)	0.0402 (4)
C10	0.40476 (8)	0.81147 (19)	0.30699 (10)	0.0431 (4)
H10	0.3716	0.8357	0.2689	0.052*
C11	0.45865 (9)	0.8669 (2)	0.31249 (11)	0.0476 (5)
H11	0.4616	0.9282	0.2786	0.057*
C12	0.50864 (8)	0.83169 (19)	0.36834 (11)	0.0453 (4)
C13	0.50374 (8)	0.7419 (2)	0.41826 (11)	0.0475 (5)
H13	0.5371	0.7176	0.4560	0.057*
C14	0.44863 (8)	0.6872 (2)	0.41224 (11)	0.0474 (5)
H14	0.4456	0.6268	0.4466	0.057*
C15	0.61272 (11)	0.8573 (4)	0.4232 (2)	0.1002 (11)
H15A	0.6096	0.8793	0.4703	0.150*
H15B	0.6457	0.9022	0.4154	0.150*
H15C	0.6188	0.7663	0.4210	0.150*
C16	0.25568 (9)	0.5548 (3)	0.38209 (14)	0.0630 (6)
H16A	0.2487	0.4941	0.3428	0.095*
H16B	0.2313	0.6293	0.3659	0.095*
H16C	0.2459	0.5160	0.4222	0.095*
C17	0.33296 (11)	0.6809 (3)	0.47360 (12)	0.0646 (6)
H17A	0.3258	0.6332	0.5128	0.097*
H17B	0.3067	0.7536	0.4621	0.097*
H17C	0.3734	0.7101	0.4881	0.097*
C18	0.37492 (8)	0.41315 (18)	0.23272 (11)	0.0416 (4)
C19	0.37935 (9)	0.2855 (2)	0.21607 (12)	0.0498 (5)
H19	0.3576	0.2247	0.2326	0.060*
C20	0.41538 (9)	0.2454 (2)	0.17531 (12)	0.0507 (5)
H20	0.4180	0.1587	0.1650	0.061*
C21	0.44721 (8)	0.3353 (2)	0.15026 (11)	0.0458 (4)
C22	0.44278 (9)	0.4630 (2)	0.16603 (13)	0.0533 (5)
H22	0.4640	0.5240	0.1488	0.064*
C23	0.40738 (9)	0.5018 (2)	0.20705 (13)	0.0508 (5)
H23	0.4052	0.5885	0.2177	0.061*
C24	0.49748 (14)	0.1779 (2)	0.10196 (17)	0.0750 (7)
H24A	0.5128	0.1402	0.1495	0.113*
H24B	0.5269	0.1721	0.0770	0.113*
H24C	0.4623	0.1326	0.0747	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0512 (3)	0.0880 (5)	0.0926 (5)	−0.0197 (3)	0.0140 (3)	0.0036 (4)
Cl2	0.1188 (7)	0.1699 (10)	0.0577 (4)	−0.0632 (6)	0.0394 (4)	−0.0210 (5)
O1	0.0641 (9)	0.0589 (10)	0.0558 (9)	0.0225 (8)	0.0008 (7)	0.0010 (7)
O2	0.0427 (7)	0.0669 (10)	0.0689 (10)	−0.0084 (7)	0.0130 (7)	0.0073 (8)
O3	0.0847 (13)	0.0963 (14)	0.0611 (11)	0.0211 (11)	0.0265 (9)	0.0364 (10)
O4	0.0632 (9)	0.0547 (9)	0.0686 (10)	0.0045 (7)	0.0332 (8)	−0.0007 (8)
N1	0.0348 (7)	0.0415 (8)	0.0421 (8)	0.0034 (6)	0.0087 (6)	0.0038 (7)
C2	0.0355 (8)	0.0449 (10)	0.0413 (9)	0.0042 (7)	0.0110 (7)	0.0027 (8)
C3	0.0389 (9)	0.0617 (13)	0.0448 (10)	0.0023 (8)	0.0146 (8)	0.0073 (9)
C4	0.0407 (9)	0.0641 (14)	0.0543 (12)	0.0010 (9)	0.0148 (9)	0.0185 (10)
C5	0.0486 (10)	0.0480 (12)	0.0609 (13)	0.0096 (9)	0.0183 (9)	0.0164 (10)
C6	0.0369 (8)	0.0398 (10)	0.0541 (11)	−0.0008 (7)	0.0143 (8)	0.0053 (8)
C7	0.0381 (9)	0.0522 (12)	0.0449 (10)	0.0084 (8)	0.0084 (8)	0.0022 (9)
C8	0.0396 (9)	0.0657 (14)	0.0514 (12)	0.0050 (9)	0.0015 (8)	−0.0046 (10)
C9	0.0384 (8)	0.0412 (10)	0.0408 (9)	0.0021 (7)	0.0117 (7)	0.0000 (8)
C10	0.0394 (9)	0.0470 (11)	0.0412 (9)	0.0023 (8)	0.0097 (7)	0.0009 (8)
C11	0.0477 (10)	0.0495 (11)	0.0462 (11)	−0.0009 (8)	0.0151 (8)	0.0052 (9)
C12	0.0398 (9)	0.0460 (11)	0.0505 (11)	−0.0016 (8)	0.0145 (8)	−0.0059 (9)
C13	0.0386 (9)	0.0509 (12)	0.0479 (11)	0.0033 (8)	0.0057 (8)	0.0023 (9)
C14	0.0426 (9)	0.0511 (12)	0.0457 (10)	0.0006 (8)	0.0093 (8)	0.0080 (9)
C15	0.0412 (12)	0.117 (3)	0.126 (3)	−0.0143 (14)	0.0005 (14)	0.044 (2)
C16	0.0400 (10)	0.0862 (18)	0.0664 (14)	−0.0007 (10)	0.0214 (10)	0.0106 (13)
C17	0.0607 (13)	0.0883 (18)	0.0478 (12)	0.0039 (12)	0.0212 (10)	0.0006 (12)
C18	0.0352 (8)	0.0387 (10)	0.0502 (10)	0.0000 (7)	0.0119 (7)	0.0025 (8)
C19	0.0501 (10)	0.0419 (11)	0.0592 (12)	−0.0088 (8)	0.0193 (9)	0.0019 (9)
C20	0.0554 (11)	0.0383 (11)	0.0584 (12)	−0.0018 (9)	0.0172 (10)	−0.0034 (9)
C21	0.0419 (9)	0.0483 (11)	0.0463 (10)	0.0025 (8)	0.0122 (8)	0.0024 (9)
C22	0.0521 (11)	0.0441 (11)	0.0693 (14)	−0.0048 (9)	0.0268 (10)	0.0041 (10)
C23	0.0504 (11)	0.0363 (10)	0.0708 (14)	−0.0005 (8)	0.0258 (10)	0.0009 (9)
C24	0.0880 (18)	0.0611 (16)	0.0897 (19)	0.0135 (13)	0.0475 (16)	−0.0023 (14)

Geometric parameters (Å, º) top

Cl1—C8	1.757 (2)	C11—C12	1.383 (3)
Cl2—C8	1.749 (2)	C11—H11	0.93
O1—C7	1.217 (2)	C12—C13	1.370 (3)
O2—C12	1.368 (2)	C13—C14	1.393 (3)
O2—C15	1.406 (3)	C13—H13	0.93
O3—C4	1.202 (3)	C14—H14	0.93
O4—C21	1.368 (2)	C15—H15A	0.96
O4—C24	1.406 (3)	C15—H15B	0.96
N1—C7	1.344 (2)	C15—H15C	0.96
N1—C6	1.483 (2)	C16—H16A	0.96
N1—C2	1.484 (2)	C16—H16B	0.96
C2—C9	1.528 (2)	C16—H16C	0.96
C2—C3	1.544 (3)	C17—H17A	0.96
C2—H2	0.98	C17—H17B	0.96
C3—C4	1.508 (3)	C17—H17C	0.96
C3—C17	1.524 (3)	C18—C19	1.377 (3)
C3—C16	1.543 (3)	C18—C23	1.383 (3)
C4—C5	1.505 (3)	C19—C20	1.387 (3)
C5—C6	1.534 (3)	C19—H19	0.93
C5—H5A	0.97	C20—C21	1.376 (3)
C5—H5B	0.97	C20—H20	0.93
C6—C18	1.521 (3)	C21—C22	1.373 (3)
C6—H6	0.98	C22—C23	1.374 (3)
C7—C8	1.533 (3)	C22—H22	0.93
C8—H8	0.98	C23—H23	0.93
C9—C14	1.380 (3)	C24—H24A	0.96
C9—C10	1.385 (3)	C24—H24B	0.96
C10—C11	1.372 (3)	C24—H24C	0.96
C10—H10	0.93

C12—O2—C15	117.99 (19)	O2—C12—C11	115.57 (18)
C21—O4—C24	117.58 (18)	C13—C12—C11	119.45 (18)
C7—N1—C6	123.51 (16)	C12—C13—C14	119.78 (18)
C7—N1—C2	116.70 (15)	C12—C13—H13	120.1
C6—N1—C2	119.19 (15)	C14—C13—H13	120.1
N1—C2—C9	109.97 (14)	C9—C14—C13	121.55 (19)
N1—C2—C3	109.99 (16)	C9—C14—H14	119.2
C9—C2—C3	118.89 (16)	C13—C14—H14	119.2
N1—C2—H2	105.7	O2—C15—H15A	109.5
C9—C2—H2	105.7	O2—C15—H15B	109.5
C3—C2—H2	105.7	H15A—C15—H15B	109.5
C4—C3—C17	112.76 (18)	O2—C15—H15C	109.5
C4—C3—C16	105.59 (19)	H15A—C15—H15C	109.5
C17—C3—C16	108.54 (17)	H15B—C15—H15C	109.5
C4—C3—C2	109.49 (15)	C3—C16—H16A	109.5
C17—C3—C2	111.01 (18)	C3—C16—H16B	109.5
C16—C3—C2	109.25 (17)	H16A—C16—H16B	109.5
O3—C4—C5	120.7 (2)	C3—C16—H16C	109.5
O3—C4—C3	122.7 (2)	H16A—C16—H16C	109.5
C5—C4—C3	116.68 (17)	H16B—C16—H16C	109.5
C4—C5—C6	118.50 (17)	C3—C17—H17A	109.5
C4—C5—H5A	107.7	C3—C17—H17B	109.5
C6—C5—H5A	107.7	H17A—C17—H17B	109.5
C4—C5—H5B	107.7	C3—C17—H17C	109.5
C6—C5—H5B	107.7	H17A—C17—H17C	109.5
H5A—C5—H5B	107.1	H17B—C17—H17C	109.5
N1—C6—C18	113.94 (15)	C19—C18—C23	117.99 (18)
N1—C6—C5	111.57 (16)	C19—C18—C6	118.50 (17)
C18—C6—C5	108.14 (15)	C23—C18—C6	123.37 (18)
N1—C6—H6	107.6	C18—C19—C20	121.69 (18)
C18—C6—H6	107.6	C18—C19—H19	119.2
C5—C6—H6	107.6	C20—C19—H19	119.2
O1—C7—N1	124.06 (19)	C21—C20—C19	119.30 (19)
O1—C7—C8	118.08 (18)	C21—C20—H20	120.3
N1—C7—C8	117.85 (18)	C19—C20—H20	120.3
C7—C8—Cl2	109.96 (16)	O4—C21—C22	115.80 (18)
C7—C8—Cl1	107.21 (15)	O4—C21—C20	124.66 (19)
Cl2—C8—Cl1	110.00 (12)	C22—C21—C20	119.54 (18)
C7—C8—H8	109.9	C21—C22—C23	120.75 (19)
Cl2—C8—H8	109.9	C21—C22—H22	119.6
Cl1—C8—H8	109.9	C23—C22—H22	119.6
C14—C9—C10	117.29 (17)	C22—C23—C18	120.72 (19)
C14—C9—C2	126.23 (17)	C22—C23—H23	119.6
C10—C9—C2	116.48 (16)	C18—C23—H23	119.6
C11—C10—C9	121.84 (18)	O4—C24—H24A	109.5
C11—C10—H10	119.1	O4—C24—H24B	109.5
C9—C10—H10	119.1	H24A—C24—H24B	109.5
C10—C11—C12	120.10 (19)	O4—C24—H24C	109.5
C10—C11—H11	120.0	H24A—C24—H24C	109.5
C12—C11—H11	120.0	H24B—C24—H24C	109.5
O2—C12—C13	124.98 (18)

C7—N1—C2—C9	−104.12 (18)	N1—C2—C9—C14	−110.8 (2)
C6—N1—C2—C9	84.47 (19)	C3—C2—C9—C14	17.3 (3)
C7—N1—C2—C3	123.10 (17)	N1—C2—C9—C10	68.9 (2)
C6—N1—C2—C3	−48.31 (19)	C3—C2—C9—C10	−163.05 (18)
N1—C2—C3—C4	60.4 (2)	C14—C9—C10—C11	0.1 (3)
C9—C2—C3—C4	−67.6 (2)	C2—C9—C10—C11	−179.62 (18)
N1—C2—C3—C17	−174.47 (15)	C9—C10—C11—C12	0.4 (3)
C9—C2—C3—C17	57.5 (2)	C15—O2—C12—C13	2.6 (3)
N1—C2—C3—C16	−54.8 (2)	C15—O2—C12—C11	−177.9 (3)
C9—C2—C3—C16	177.18 (18)	C10—C11—C12—O2	−179.95 (18)
C17—C3—C4—O3	29.1 (3)	C10—C11—C12—C13	−0.5 (3)
C16—C3—C4—O3	−89.2 (3)	O2—C12—C13—C14	179.43 (19)
C2—C3—C4—O3	153.3 (2)	C11—C12—C13—C14	0.0 (3)
C17—C3—C4—C5	−150.11 (19)	C10—C9—C14—C13	−0.6 (3)
C16—C3—C4—C5	91.5 (2)	C2—C9—C14—C13	179.11 (18)
C2—C3—C4—C5	−26.0 (2)	C12—C13—C14—C9	0.5 (3)
O3—C4—C5—C6	158.4 (2)	N1—C6—C18—C19	−160.22 (17)
C3—C4—C5—C6	−22.3 (3)	C5—C6—C18—C19	75.1 (2)
C7—N1—C6—C18	66.7 (2)	N1—C6—C18—C23	24.2 (3)
C2—N1—C6—C18	−122.54 (17)	C5—C6—C18—C23	−100.5 (2)
C7—N1—C6—C5	−170.53 (17)	C23—C18—C19—C20	0.4 (3)
C2—N1—C6—C5	0.3 (2)	C6—C18—C19—C20	−175.39 (19)
C4—C5—C6—N1	36.3 (2)	C18—C19—C20—C21	−0.5 (3)
C4—C5—C6—C18	162.32 (18)	C24—O4—C21—C22	169.2 (2)
C6—N1—C7—O1	178.95 (18)	C24—O4—C21—C20	−11.7 (3)
C2—N1—C7—O1	7.9 (3)	C19—C20—C21—O4	−179.0 (2)
C6—N1—C7—C8	−0.6 (3)	C19—C20—C21—C22	0.0 (3)
C2—N1—C7—C8	−171.63 (16)	O4—C21—C22—C23	179.7 (2)
O1—C7—C8—Cl2	49.9 (2)	C20—C21—C22—C23	0.6 (3)
N1—C7—C8—Cl2	−130.51 (17)	C21—C22—C23—C18	−0.7 (4)
O1—C7—C8—Cl1	−69.7 (2)	C19—C18—C23—C22	0.2 (3)
N1—C7—C8—Cl1	109.92 (18)	C6—C18—C23—C22	175.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.98	2.30	3.216 (2)	155
C13—H13···O3ⁱⁱ	0.93	2.58	3.453 (3)	155

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅Cl₂NO₄
M_r	450.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	23.6295 (9), 10.3999 (4), 19.2617 (9)
β (°)	107.734 (1)
V (Å³)	4508.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.911, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	29354, 6905, 4138
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.184, 1.01
No. of reflections	6905
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.63

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.98	2.30	3.216 (2)	155
C13—H13···O3ⁱⁱ	0.93	2.58	3.453 (3)	155

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

SP thanks the UGC, India, for financial support.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
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 (2004). APEX2 and SAINT. 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
Eller, K., Henkes, E., Rossbacher, R. & Hoke, H. (2002). Amines, Aliphatic, in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 1, p. 379. Weinheim: Wiley-VCH Verlag. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ribeiro da Silva, M. A. V. & Cabral, J. I. T. A. (2007). J. Therm. Anal. Calorim. 90, 865–871. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. 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)-c-3,t-3-di­methyl­piperidin-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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