r-2,c-6-Bis(4-chloro-phen-yl)-c-3,t-3-dimethyl-piperidin-4-one.

In the title mol-ecule, C(19)H(19)Cl(2)NO, the piperidine ring adopts a chair conformation and the dihedral angle between the two benzene rings is 77.23 (7)°. In the crystal structure, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, and a weak C-H⋯π inter-action is also observed.

Related literature

For a related crystal structure, see: Gayathri et al. (2008 ▶). For background on the biological activities of piperidones, see: Dimmock et al. (2001 ▶); Perumal et al. (2001 ▶). For the synthesis and stereodynamics of piperidin-4-ones and their derivatives, see: Ponnuswamy et al. (2002 ▶). For the synthesis, see: Noller & Baliah (1948 ▶).

Experimental

Crystal data

C19H19Cl2NO

M = 348.25

Orthorhombic,

a = 13.1627 (5) Å

b = 22.4739 (7) Å

c = 5.8794 (2) Å

V = 1739.23 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 200 (2) K

0.44 × 0.31 × 0.22 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.950, T max = 1.000 (expected range = 0.874–0.920)

19147 measured reflections

5694 independent reflections

2460 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.083

S = 0.82

5694 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 2278 Friedel pairs

Flack parameter: −0.03 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036325/hb2832sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036325/hb2832Isup2.hkl

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

C19H19Cl2NO	Dx = 1.330 Mg m−3
Mr = 348.25	Melting point: 402(1) K
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4389 reflections
a = 13.1627 (5) Å	θ = 4.5–32.5º
b = 22.4739 (7) Å	µ = 0.38 mm−1
c = 5.8794 (2) Å	T = 200 (2) K
V = 1739.23 (10) Å3	Rectangular-plate, colourless
Z = 4	0.44 × 0.31 × 0.22 mm
F000 = 728

Oxford Diffraction R Gemini diffractometer	5694 independent reflections
Radiation source: fine-focus sealed tube	2460 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.052
Detector resolution: 10.5081 pixels mm-1	θmax = 32.5º
T = 200(2) K	θmin = 4.7º
φ and ω scans	h = −18→19
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	k = −33→33
Tmin = 0.950, Tmax = 1.000	l = −8→8
19147 measured reflections

Refinement on F2	Hydrogen site location: difmap and geom
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083	(Δ/σ)max = 0.001
S = 0.82	Δρmax = 0.34 e Å−3
5694 reflections	Δρmin = −0.31 e Å−3
212 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 2278 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (5)
Secondary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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	0.03898 (4)	0.45263 (2)	0.55799 (11)	0.0585 (2)
Cl2	0.10182 (5)	−0.04812 (2)	1.04537 (12)	0.0655 (2)
O4	0.57022 (11)	0.24936 (6)	1.2121 (2)	0.0424 (5)
N1	0.28387 (13)	0.22418 (6)	1.0183 (3)	0.0312 (5)
C2	0.32122 (13)	0.28540 (7)	1.0528 (3)	0.0277 (5)
C3	0.43587 (14)	0.28927 (8)	0.9833 (3)	0.0307 (6)
C4	0.49124 (15)	0.23934 (9)	1.1093 (3)	0.0341 (6)
C5	0.44531 (14)	0.17905 (9)	1.1022 (4)	0.0411 (7)
C6	0.33289 (15)	0.18081 (8)	1.1659 (3)	0.0321 (6)
C21	0.25298 (15)	0.32842 (8)	0.9275 (3)	0.0312 (6)
C22	0.21068 (13)	0.31249 (8)	0.7180 (3)	0.0314 (6)
C23	0.14602 (14)	0.35069 (8)	0.6055 (3)	0.0345 (6)
C24	0.12245 (15)	0.40493 (8)	0.7019 (3)	0.0352 (6)
C25	0.16202 (16)	0.42206 (8)	0.9082 (3)	0.0377 (7)
C26	0.22727 (14)	0.38327 (8)	1.0207 (3)	0.0347 (6)
C31	0.47926 (14)	0.34992 (8)	1.0480 (4)	0.0439 (7)
C32	0.45062 (15)	0.27850 (10)	0.7274 (3)	0.0426 (7)
C61	0.27905 (14)	0.12205 (8)	1.1398 (3)	0.0305 (6)
C62	0.28440 (17)	0.08976 (9)	0.9400 (3)	0.0439 (7)
C63	0.23098 (19)	0.03820 (9)	0.9104 (4)	0.0504 (8)
C64	0.17155 (15)	0.01751 (8)	1.0837 (4)	0.0424 (7)
C65	0.16451 (18)	0.04755 (10)	1.2868 (4)	0.0461 (8)
C66	0.21822 (16)	0.09989 (10)	1.3129 (3)	0.0432 (8)
H1	0.2194 (13)	0.2237 (7)	1.032 (3)	0.023 (5)*
H2	0.31631	0.29460	1.21887	0.0333*
H5A	0.48191	0.15262	1.20910	0.0493*
H5B	0.45276	0.16236	0.94724	0.0493*
H6	0.32639	0.19436	1.32722	0.0385*
H22	0.22667	0.27498	0.65262	0.0376*
H23	0.11790	0.33976	0.46270	0.0414*
H25	0.14517	0.45957	0.97251	0.0452*
H26	0.25477	0.39444	1.16384	0.0416*
H31A	0.44241	0.38120	0.96623	0.0659*
H31B	0.55139	0.35148	1.00700	0.0659*
H31C	0.47187	0.35603	1.21217	0.0659*
H32A	0.41564	0.30973	0.64133	0.0639*
H32B	0.42235	0.23962	0.68637	0.0639*
H32C	0.52328	0.27930	0.69113	0.0639*
H62	0.32636	0.10380	0.81998	0.0527*
H63	0.23513	0.01699	0.77096	0.0605*
H65	0.12350	0.03259	1.40682	0.0553*
H66	0.21343	0.12114	1.45215	0.0519*

	U11	U22	U33	U12	U13	U23
Cl1	0.0547 (3)	0.0505 (3)	0.0703 (4)	0.0179 (3)	−0.0132 (4)	0.0120 (3)
Cl2	0.0681 (4)	0.0421 (3)	0.0864 (4)	−0.0195 (3)	−0.0183 (4)	0.0074 (3)
O4	0.0273 (8)	0.0530 (9)	0.0468 (8)	−0.0024 (7)	−0.0046 (8)	0.0054 (7)
N1	0.0184 (9)	0.0324 (8)	0.0427 (10)	0.0015 (7)	−0.0010 (8)	0.0036 (7)
C2	0.0273 (10)	0.0267 (9)	0.0292 (9)	0.0009 (8)	0.0047 (10)	0.0017 (10)
C3	0.0262 (11)	0.0338 (10)	0.0321 (10)	−0.0012 (9)	0.0015 (9)	0.0010 (8)
C4	0.0225 (10)	0.0414 (12)	0.0385 (11)	0.0026 (9)	0.0030 (10)	−0.0003 (9)
C5	0.0293 (11)	0.0359 (11)	0.0581 (14)	0.0052 (9)	−0.0109 (11)	0.0094 (11)
C6	0.0329 (11)	0.0306 (10)	0.0328 (9)	0.0049 (9)	−0.0053 (9)	0.0087 (8)
C21	0.0223 (10)	0.0374 (12)	0.0339 (10)	−0.0015 (9)	0.0035 (9)	−0.0045 (9)
C22	0.0337 (11)	0.0273 (10)	0.0331 (10)	−0.0018 (9)	−0.0029 (10)	−0.0017 (8)
C23	0.0307 (11)	0.0362 (10)	0.0366 (11)	0.0023 (9)	−0.0043 (9)	0.0008 (9)
C24	0.0306 (11)	0.0327 (11)	0.0424 (11)	0.0012 (9)	−0.0018 (10)	0.0117 (10)
C25	0.0354 (12)	0.0304 (11)	0.0472 (11)	0.0037 (10)	0.0028 (11)	−0.0011 (10)
C26	0.0282 (10)	0.0364 (10)	0.0394 (10)	0.0017 (9)	−0.0005 (10)	−0.0045 (9)
C31	0.0355 (11)	0.0386 (11)	0.0577 (12)	−0.0024 (9)	−0.0058 (13)	−0.0094 (11)
C32	0.0360 (13)	0.0550 (14)	0.0368 (11)	−0.0003 (10)	0.0049 (11)	0.0074 (11)
C61	0.0304 (11)	0.0246 (9)	0.0364 (10)	0.0045 (9)	−0.0026 (9)	0.0077 (8)
C62	0.0537 (15)	0.0387 (12)	0.0393 (11)	−0.0057 (11)	0.0080 (11)	0.0021 (10)
C63	0.0657 (17)	0.0362 (13)	0.0493 (12)	−0.0036 (12)	−0.0009 (14)	−0.0095 (11)
C64	0.0390 (12)	0.0308 (10)	0.0573 (14)	−0.0048 (9)	−0.0099 (13)	0.0126 (12)
C65	0.0384 (14)	0.0485 (14)	0.0514 (13)	−0.0074 (11)	−0.0026 (11)	0.0076 (11)
C66	0.0445 (14)	0.0455 (14)	0.0397 (11)	−0.0003 (12)	−0.0064 (11)	0.0015 (10)

Cl1—C24	1.7528 (19)	C62—C63	1.367 (3)
Cl2—C64	1.7518 (19)	C63—C64	1.366 (3)
O4—C4	1.223 (2)	C64—C65	1.375 (3)
N1—C2	1.475 (2)	C65—C66	1.381 (3)
N1—C6	1.456 (2)	C2—H2	1.0000
N1—H1	0.853 (17)	C5—H5A	0.9900
C2—C3	1.566 (3)	C5—H5B	0.9900
C2—C21	1.511 (2)	C6—H6	1.0000
C3—C31	1.526 (3)	C22—H22	0.9500
C3—C32	1.536 (3)	C23—H23	0.9500
C3—C4	1.529 (3)	C25—H25	0.9500
C4—C5	1.484 (3)	C26—H26	0.9500
C5—C6	1.527 (3)	C31—H31A	0.9800
C6—C61	1.507 (3)	C31—H31B	0.9800
C21—C22	1.398 (3)	C31—H31C	0.9800
C21—C26	1.391 (3)	C32—H32A	0.9800
C22—C23	1.378 (3)	C32—H32B	0.9800
C23—C24	1.380 (3)	C32—H32C	0.9800
C24—C25	1.375 (3)	C62—H62	0.9500
C25—C26	1.391 (3)	C63—H63	0.9500
C61—C66	1.387 (3)	C65—H65	0.9500
C61—C62	1.383 (3)	C66—H66	0.9500
C2—N1—C6	113.25 (15)	N1—C2—H2	108.00
C6—N1—H1	112.1 (11)	C3—C2—H2	108.00
C2—N1—H1	109.3 (11)	C21—C2—H2	108.00
N1—C2—C21	109.36 (14)	C4—C5—H5A	109.00
N1—C2—C3	109.70 (14)	C4—C5—H5B	109.00
C3—C2—C21	114.21 (14)	C6—C5—H5A	109.00
C2—C3—C31	110.20 (14)	C6—C5—H5B	109.00
C2—C3—C4	106.98 (14)	H5A—C5—H5B	108.00
C4—C3—C32	107.37 (15)	N1—C6—H6	109.00
C31—C3—C32	109.73 (16)	C5—C6—H6	109.00
C4—C3—C31	110.87 (15)	C61—C6—H6	109.00
C2—C3—C32	111.63 (15)	C21—C22—H22	120.00
O4—C4—C5	121.87 (18)	C23—C22—H22	120.00
O4—C4—C3	120.61 (17)	C22—C23—H23	120.00
C3—C4—C5	117.52 (16)	C24—C23—H23	120.00
C4—C5—C6	111.36 (16)	C24—C25—H25	121.00
N1—C6—C5	107.50 (15)	C26—C25—H25	121.00
C5—C6—C61	114.09 (16)	C21—C26—H26	119.00
N1—C6—C61	108.52 (15)	C25—C26—H26	119.00
C2—C21—C26	121.30 (16)	C3—C31—H31A	109.00
C2—C21—C22	120.15 (16)	C3—C31—H31B	109.00
C22—C21—C26	118.50 (17)	C3—C31—H31C	109.00
C21—C22—C23	120.61 (17)	H31A—C31—H31B	109.00
C22—C23—C24	119.48 (17)	H31A—C31—H31C	109.00
C23—C24—C25	121.64 (17)	H31B—C31—H31C	109.00
Cl1—C24—C25	119.47 (14)	C3—C32—H32A	109.00
Cl1—C24—C23	118.88 (14)	C3—C32—H32B	109.00
C24—C25—C26	118.54 (17)	C3—C32—H32C	109.00
C21—C26—C25	121.22 (17)	H32A—C32—H32B	109.00
C62—C61—C66	117.66 (18)	H32A—C32—H32C	109.00
C6—C61—C62	121.51 (17)	H32B—C32—H32C	109.00
C6—C61—C66	120.76 (16)	C61—C62—H62	119.00
C61—C62—C63	121.81 (19)	C63—C62—H62	119.00
C62—C63—C64	119.2 (2)	C62—C63—H63	120.00
Cl2—C64—C65	119.33 (17)	C64—C63—H63	120.00
Cl2—C64—C63	119.38 (17)	C64—C65—H65	121.00
C63—C64—C65	121.28 (19)	C66—C65—H65	121.00
C64—C65—C66	118.7 (2)	C61—C66—H66	119.00
C61—C66—C65	121.31 (18)	C65—C66—H66	119.00
C6—N1—C2—C3	64.86 (19)	N1—C6—C61—C62	68.3 (2)
C6—N1—C2—C21	−169.16 (15)	N1—C6—C61—C66	−108.6 (2)
C2—N1—C6—C5	−64.02 (19)	C5—C6—C61—C62	−51.5 (2)
C2—N1—C6—C61	172.13 (15)	C5—C6—C61—C66	131.6 (2)
N1—C2—C3—C4	−51.75 (18)	C2—C21—C22—C23	178.11 (17)
N1—C2—C3—C31	−172.37 (15)	C26—C21—C22—C23	0.8 (3)
N1—C2—C3—C32	65.44 (19)	C2—C21—C26—C25	−178.05 (17)
C21—C2—C3—C4	−174.92 (14)	C22—C21—C26—C25	−0.8 (3)
C21—C2—C3—C31	64.5 (2)	C21—C22—C23—C24	−0.5 (3)
C21—C2—C3—C32	−57.7 (2)	C22—C23—C24—Cl1	−179.30 (14)
N1—C2—C21—C22	−36.1 (2)	C22—C23—C24—C25	0.1 (3)
N1—C2—C21—C26	141.12 (18)	Cl1—C24—C25—C26	179.33 (15)
C3—C2—C21—C22	87.3 (2)	C23—C24—C25—C26	−0.1 (3)
C3—C2—C21—C26	−95.5 (2)	C24—C25—C26—C21	0.4 (3)
C2—C3—C4—O4	−132.07 (17)	C6—C61—C62—C63	−176.1 (2)
C2—C3—C4—C5	47.7 (2)	C66—C61—C62—C63	0.9 (3)
C31—C3—C4—O4	−11.9 (2)	C6—C61—C66—C65	176.77 (19)
C31—C3—C4—C5	167.88 (17)	C62—C61—C66—C65	−0.2 (3)
C32—C3—C4—O4	107.97 (19)	C61—C62—C63—C64	−0.8 (3)
C32—C3—C4—C5	−72.3 (2)	C62—C63—C64—Cl2	179.29 (17)
O4—C4—C5—C6	129.70 (19)	C62—C63—C64—C65	0.0 (3)
C3—C4—C5—C6	−50.1 (2)	Cl2—C64—C65—C66	−178.65 (17)
C4—C5—C6—N1	53.9 (2)	C63—C64—C65—C66	0.6 (3)
C4—C5—C6—C61	174.28 (16)	C64—C65—C66—C61	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.853 (17)	2.312 (17)	3.092 (2)	152.3 (15)
C23—H23···O4ii	0.95	2.56	3.377 (2)	144
C31—H31B···Cg1iii	0.98	2.96	3.7265 (15)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.853 (17)	2.312 (17)	3.092 (2)	152.3 (15)
C23—H23⋯O4ii	0.95	2.56	3.377 (2)	144
C31—H31B⋯Cg1iii	0.98	2.96	3.7265 (15)	136

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C61–C66 ring.