1-Dichloro-acetyl-t-3,t-5-dimethyl-r-2,c-6-diphenyl-piperidin-4-one.

In the title compound, C21H21Cl2NO2, the piperidine ring adopts a distorted boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend angles of 87.9 (7) and 70.8 (9)°, respectively, with the best plane through the piperidine ring. In the crystal, mol-ecules are connected by C-H⋯O and C-H⋯Cl inter-actions into layers in the ab plane.

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ▶); Michael (2001 ▶); Pinder (1992 ▶); Rubiralta et al. (1991 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al.(1995 ▶).

Experimental

Crystal data

C21H21Cl2NO2

M = 390.29

Monoclinic,

a = 8.278 (2) Å

b = 9.714 (3) Å

c = 11.847 (3) Å

β = 90.578 (9)°

V = 952.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 293 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.931, T max = 0.944

8874 measured reflections

4241 independent reflections

3962 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.03

4241 reflections

235 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 1745 Friedel pairs

Flack parameter: 0.01 (5)

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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007927/bt6893sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007927/bt6893Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007927/bt6893Isup3.cml

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

C21H21Cl2NO2	F(000) = 408
Mr = 390.29	Dx = 1.361 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3962 reflections
a = 8.278 (2) Å	θ = 1.7–28.4°
b = 9.714 (3) Å	µ = 0.36 mm−1
c = 11.847 (3) Å	T = 293 K
β = 90.578 (9)°	Block, white crystalline
V = 952.5 (5) Å3	0.20 × 0.18 × 0.17 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	4241 independent reflections
Radiation source: fine-focus sealed tube	3962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.931, Tmax = 0.944	k = −11→12
8874 measured reflections	l = −15→15

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.1557P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4241 reflections	Δρmax = 0.31 e Å−3
235 parameters	Δρmin = −0.31 e Å−3
1 restraint	Absolute structure: Flack (1983), 1745 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

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
C2	0.41560 (17)	0.55485 (16)	0.18606 (12)	0.0275 (3)
H2	0.4759	0.5181	0.1220	0.033*
C3	0.42988 (17)	0.71381 (17)	0.18432 (12)	0.0298 (3)
H3	0.3622	0.7493	0.2452	0.036*
C4	0.35940 (19)	0.76681 (17)	0.07391 (12)	0.0321 (3)
C5	0.19801 (19)	0.7045 (2)	0.03920 (12)	0.0349 (3)
H5	0.1242	0.7795	0.0186	0.042*
C6	0.12278 (18)	0.62258 (17)	0.13576 (13)	0.0315 (3)
H6	0.0301	0.5735	0.1030	0.038*
C7	0.05790 (17)	0.70465 (19)	0.23542 (12)	0.0332 (3)
C8	0.0412 (2)	0.8464 (2)	0.23415 (16)	0.0434 (4)
H8	0.0746	0.8959	0.1714	0.052*
C9	−0.0246 (2)	0.9155 (2)	0.32501 (19)	0.0522 (5)
H9	−0.0357	1.0107	0.3226	0.063*
C10	−0.0736 (2)	0.8441 (3)	0.41870 (17)	0.0537 (5)
H10	−0.1167	0.8908	0.4800	0.064*
C11	−0.0585 (2)	0.7033 (3)	0.42115 (16)	0.0523 (5)
H11	−0.0920	0.6545	0.4843	0.063*
C12	0.0064 (2)	0.6335 (2)	0.33014 (15)	0.0425 (4)
H12	0.0155	0.5381	0.3326	0.051*
C13	0.49049 (18)	0.49813 (17)	0.29406 (13)	0.0328 (3)
C14	0.4205 (2)	0.5223 (2)	0.39840 (14)	0.0430 (4)
H14	0.3252	0.5726	0.4032	0.052*
C15	0.4943 (3)	0.4706 (3)	0.49568 (18)	0.0602 (6)
H15	0.4470	0.4852	0.5655	0.072*
C16	0.6365 (3)	0.3980 (3)	0.4893 (2)	0.0650 (7)
H16	0.6850	0.3642	0.5548	0.078*
C17	0.7073 (3)	0.3752 (3)	0.3867 (2)	0.0596 (6)
H17	0.8035	0.3259	0.3828	0.071*
C18	0.6351 (2)	0.4259 (2)	0.28862 (17)	0.0424 (4)
H18	0.6838	0.4115	0.2192	0.051*
C19	0.1845 (2)	0.38367 (19)	0.17034 (15)	0.0373 (3)
C20	0.3085 (2)	0.26688 (18)	0.17704 (14)	0.0373 (3)
H20	0.4172	0.3033	0.1639	0.045*
C21	0.6019 (2)	0.7649 (2)	0.20659 (16)	0.0467 (4)
H21A	0.6406	0.7286	0.2772	0.070*
H21B	0.6022	0.8637	0.2097	0.070*
H21C	0.6709	0.7346	0.1469	0.070*
C22	0.2237 (3)	0.6139 (2)	−0.06545 (14)	0.0496 (5)
H22A	0.1226	0.5737	−0.0883	0.074*
H22B	0.2995	0.5422	−0.0476	0.074*
H22C	0.2649	0.6693	−0.1258	0.074*
N1	0.24080 (15)	0.51501 (14)	0.17151 (10)	0.0289 (3)
O1	0.42761 (17)	0.84953 (16)	0.01538 (11)	0.0479 (3)
O2	0.04081 (17)	0.35524 (17)	0.16311 (17)	0.0645 (4)
Cl1	0.25867 (8)	0.14398 (5)	0.07228 (5)	0.06394 (16)
Cl2	0.30062 (9)	0.18963 (7)	0.31158 (5)	0.07162 (19)

	U11	U22	U33	U12	U13	U23
C2	0.0262 (6)	0.0266 (8)	0.0297 (6)	−0.0013 (5)	−0.0018 (5)	0.0000 (5)
C3	0.0304 (7)	0.0279 (8)	0.0310 (6)	−0.0042 (6)	−0.0020 (5)	0.0007 (6)
C4	0.0377 (8)	0.0263 (8)	0.0324 (7)	0.0037 (6)	0.0017 (6)	0.0005 (6)
C5	0.0378 (7)	0.0354 (9)	0.0315 (7)	0.0045 (7)	−0.0055 (6)	0.0027 (6)
C6	0.0287 (7)	0.0307 (8)	0.0349 (7)	0.0009 (6)	−0.0062 (5)	−0.0001 (6)
C7	0.0242 (6)	0.0358 (8)	0.0395 (7)	0.0013 (6)	−0.0021 (5)	−0.0009 (7)
C8	0.0412 (8)	0.0362 (10)	0.0530 (10)	0.0021 (7)	0.0023 (7)	0.0015 (8)
C9	0.0440 (10)	0.0418 (12)	0.0707 (13)	0.0046 (8)	0.0006 (9)	−0.0132 (10)
C10	0.0371 (9)	0.0712 (15)	0.0527 (11)	0.0061 (9)	0.0005 (7)	−0.0208 (10)
C11	0.0452 (9)	0.0680 (14)	0.0440 (9)	0.0016 (10)	0.0077 (7)	−0.0004 (10)
C12	0.0377 (8)	0.0437 (10)	0.0461 (8)	0.0023 (7)	0.0044 (6)	0.0034 (8)
C13	0.0331 (7)	0.0290 (8)	0.0360 (7)	−0.0048 (6)	−0.0061 (6)	0.0041 (6)
C14	0.0417 (9)	0.0524 (12)	0.0348 (8)	−0.0064 (8)	−0.0040 (6)	0.0025 (8)
C15	0.0681 (13)	0.0767 (17)	0.0357 (8)	−0.0239 (12)	−0.0115 (8)	0.0103 (9)
C16	0.0658 (14)	0.0669 (16)	0.0615 (13)	−0.0179 (12)	−0.0338 (11)	0.0273 (12)
C17	0.0469 (10)	0.0527 (13)	0.0785 (15)	0.0011 (9)	−0.0264 (10)	0.0176 (11)
C18	0.0376 (8)	0.0378 (10)	0.0517 (9)	0.0007 (7)	−0.0084 (7)	0.0055 (8)
C19	0.0361 (8)	0.0298 (9)	0.0458 (8)	−0.0041 (6)	−0.0025 (6)	−0.0042 (7)
C20	0.0464 (9)	0.0239 (8)	0.0417 (8)	−0.0052 (7)	0.0032 (7)	0.0003 (6)
C21	0.0419 (9)	0.0450 (11)	0.0530 (10)	−0.0171 (8)	−0.0098 (7)	0.0057 (8)
C22	0.0630 (11)	0.0531 (14)	0.0325 (8)	−0.0012 (9)	−0.0049 (7)	−0.0057 (8)
N1	0.0272 (6)	0.0259 (7)	0.0335 (6)	−0.0021 (5)	−0.0038 (4)	−0.0011 (5)
O1	0.0553 (7)	0.0419 (8)	0.0468 (7)	−0.0025 (6)	0.0068 (6)	0.0151 (6)
O2	0.0394 (7)	0.0393 (9)	0.1147 (14)	−0.0121 (6)	−0.0077 (8)	−0.0083 (9)
Cl1	0.0835 (4)	0.0399 (3)	0.0688 (3)	−0.0167 (3)	0.0168 (3)	−0.0214 (2)
Cl2	0.0933 (4)	0.0638 (4)	0.0576 (3)	−0.0154 (3)	−0.0061 (3)	0.0249 (3)

C2—N1	1.5060 (19)	C12—H12	0.9300
C2—C13	1.519 (2)	C13—C18	1.390 (2)
C2—C3	1.549 (2)	C13—C14	1.390 (2)
C2—H2	0.9800	C14—C15	1.393 (3)
C3—C4	1.517 (2)	C14—H14	0.9300
C3—C21	1.528 (2)	C15—C16	1.375 (4)
C3—H3	0.9800	C15—H15	0.9300
C4—O1	1.205 (2)	C16—C17	1.372 (4)
C4—C5	1.520 (2)	C16—H16	0.9300
C5—C6	1.531 (2)	C17—C18	1.392 (3)
C5—C22	1.537 (2)	C17—H17	0.9300
C5—H5	0.9800	C18—H18	0.9300
C6—N1	1.489 (2)	C19—O2	1.224 (2)
C6—C7	1.527 (2)	C19—N1	1.358 (2)
C6—H6	0.9800	C19—C20	1.531 (3)
C7—C8	1.384 (3)	C20—Cl2	1.7634 (18)
C7—C12	1.389 (2)	C20—Cl1	1.7679 (18)
C8—C9	1.385 (3)	C20—H20	0.9800
C8—H8	0.9300	C21—H21A	0.9600
C9—C10	1.373 (3)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.373 (4)	C22—H22A	0.9600
C10—H10	0.9300	C22—H22B	0.9600
C11—C12	1.387 (3)	C22—H22C	0.9600
C11—H11	0.9300
N1—C2—C13	112.74 (12)	C7—C12—H12	119.7
N1—C2—C3	109.15 (12)	C18—C13—C14	119.57 (15)
C13—C2—C3	110.01 (12)	C18—C13—C2	119.23 (14)
N1—C2—H2	108.3	C14—C13—C2	121.15 (15)
C13—C2—H2	108.3	C13—C14—C15	119.4 (2)
C3—C2—H2	108.3	C13—C14—H14	120.3
C4—C3—C21	112.84 (14)	C15—C14—H14	120.3
C4—C3—C2	108.73 (12)	C16—C15—C14	120.5 (2)
C21—C3—C2	113.12 (14)	C16—C15—H15	119.7
C4—C3—H3	107.3	C14—C15—H15	119.7
C21—C3—H3	107.3	C17—C16—C15	120.35 (18)
C2—C3—H3	107.3	C17—C16—H16	119.8
O1—C4—C3	122.95 (15)	C15—C16—H16	119.8
O1—C4—C5	121.70 (15)	C16—C17—C18	119.9 (2)
C3—C4—C5	115.32 (13)	C16—C17—H17	120.1
C4—C5—C6	111.58 (12)	C18—C17—H17	120.1
C4—C5—C22	108.55 (14)	C13—C18—C17	120.20 (19)
C6—C5—C22	111.46 (16)	C13—C18—H18	119.9
C4—C5—H5	108.4	C17—C18—H18	119.9
C6—C5—H5	108.4	O2—C19—N1	123.08 (17)
C22—C5—H5	108.4	O2—C19—C20	119.15 (17)
N1—C6—C7	112.41 (12)	N1—C19—C20	117.76 (14)
N1—C6—C5	107.86 (12)	C19—C20—Cl2	109.33 (12)
C7—C6—C5	117.09 (14)	C19—C20—Cl1	108.19 (12)
N1—C6—H6	106.3	Cl2—C20—Cl1	109.67 (10)
C7—C6—H6	106.3	C19—C20—H20	109.9
C5—C6—H6	106.3	Cl2—C20—H20	109.9
C8—C7—C12	118.20 (17)	Cl1—C20—H20	109.9
C8—C7—C6	123.16 (15)	C3—C21—H21A	109.5
C12—C7—C6	118.58 (17)	C3—C21—H21B	109.5
C7—C8—C9	120.92 (18)	H21A—C21—H21B	109.5
C7—C8—H8	119.5	C3—C21—H21C	109.5
C9—C8—H8	119.5	H21A—C21—H21C	109.5
C10—C9—C8	120.4 (2)	H21B—C21—H21C	109.5
C10—C9—H9	119.8	C5—C22—H22A	109.5
C8—C9—H9	119.8	C5—C22—H22B	109.5
C9—C10—C11	119.47 (19)	H22A—C22—H22B	109.5
C9—C10—H10	120.3	C5—C22—H22C	109.5
C11—C10—H10	120.3	H22A—C22—H22C	109.5
C10—C11—C12	120.4 (2)	H22B—C22—H22C	109.5
C10—C11—H11	119.8	C19—N1—C6	115.62 (13)
C12—C11—H11	119.8	C19—N1—C2	124.85 (13)
C11—C12—C7	120.6 (2)	C6—N1—C2	118.62 (12)
C11—C12—H12	119.7
N1—C2—C3—C4	−57.74 (15)	N1—C2—C13—C18	128.73 (16)
C13—C2—C3—C4	178.07 (11)	C3—C2—C13—C18	−109.19 (17)
N1—C2—C3—C21	176.08 (12)	N1—C2—C13—C14	−54.1 (2)
C13—C2—C3—C21	51.89 (17)	C3—C2—C13—C14	68.04 (19)
C21—C3—C4—O1	−5.9 (2)	C18—C13—C14—C15	−1.7 (3)
C2—C3—C4—O1	−132.20 (17)	C2—C13—C14—C15	−178.90 (18)
C21—C3—C4—C5	172.05 (15)	C13—C14—C15—C16	1.0 (3)
C2—C3—C4—C5	45.70 (17)	C14—C15—C16—C17	−0.2 (4)
O1—C4—C5—C6	−170.08 (16)	C15—C16—C17—C18	0.1 (4)
C3—C4—C5—C6	12.0 (2)	C14—C13—C18—C17	1.6 (3)
O1—C4—C5—C22	66.7 (2)	C2—C13—C18—C17	178.85 (18)
C3—C4—C5—C22	−111.23 (16)	C16—C17—C18—C13	−0.8 (3)
C4—C5—C6—N1	−56.95 (17)	O2—C19—C20—Cl2	−73.1 (2)
C22—C5—C6—N1	64.59 (16)	N1—C19—C20—Cl2	107.58 (16)
C4—C5—C6—C7	70.99 (17)	O2—C19—C20—Cl1	46.2 (2)
C22—C5—C6—C7	−167.47 (14)	N1—C19—C20—Cl1	−133.03 (14)
N1—C6—C7—C8	136.15 (16)	O2—C19—N1—C6	−14.3 (3)
C5—C6—C7—C8	10.4 (2)	C20—C19—N1—C6	164.98 (13)
N1—C6—C7—C12	−46.81 (19)	O2—C19—N1—C2	176.81 (17)
C5—C6—C7—C12	−172.51 (14)	C20—C19—N1—C2	−3.9 (2)
C12—C7—C8—C9	0.2 (3)	C7—C6—N1—C19	104.61 (16)
C6—C7—C8—C9	177.28 (16)	C5—C6—N1—C19	−124.81 (15)
C7—C8—C9—C10	0.4 (3)	C7—C6—N1—C2	−85.74 (16)
C8—C9—C10—C11	−0.7 (3)	C5—C6—N1—C2	44.84 (17)
C9—C10—C11—C12	0.3 (3)	C13—C2—N1—C19	−56.66 (19)
C10—C11—C12—C7	0.4 (3)	C3—C2—N1—C19	−179.22 (14)
C8—C7—C12—C11	−0.6 (3)	C13—C2—N1—C6	134.73 (14)
C6—C7—C12—C11	−177.81 (15)	C3—C2—N1—C6	12.16 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.98	2.45	3.379 (2)	159
C20—H20···O1i	0.98	2.53	3.273 (2)	132
C21—H21C···Cl1ii	0.96	2.81	3.702 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.45	3.379 (2)	159
C20—H20⋯O1i	0.98	2.53	3.273 (2)	132
C21—H21C⋯Cl1ii	0.96	2.81	3.702 (2)	155

Symmetry codes: (i) ; (ii) .