Crystal structure of 2-chloro-1-(3-methyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

In the title compound, C20H22ClNO, the piperidine ring has a twist-boat conformation. There is an intra-molecular C-H⋯π inter-action involving the two phenyl rings which are inclined to one another by 84.91 (7)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming helical chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (100).

Related literature

For the biological activity of piperidines and their derivatives, see: Aridoss et al. (2007 ▸); Jain et al. (2005 ▸); Mobio et al. (1989 ▸); Palani et al. (2002 ▸). For the crystal structure of a very similar compound, 2-chloro-1-(3,3-dimethyl-2,6-di­phenyl­piperidin-1-yl)ethanone, see: Prathebha et al. (2013 ▸).

Experimental

Crystal data

C20H22ClNO

M = 327.84

Monoclinic,

a = 8.7146 (3) Å

b = 12.3963 (4) Å

c = 16.6117 (6) Å

β = 101.523 (2)°

V = 1758.37 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.25 × 0.23 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.946, T max = 0.950

16473 measured reflections

4353 independent reflections

3075 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.236

S = 0.92

4353 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.38 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, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901500122X/su5068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500122X/su5068Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500122X/su5068Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500122X/su5068fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular C—H⋯π inter­action is shown as a dashed line (see Table 1 for details).

Click here for additional data file.

a . DOI: 10.1107/S205698901500122X/su5068fig2.tif

A view along the a axis of the crystal packing of the title compound. The dashed lines indicate the hydrogen bonds (see Table 1 for details).

CCDC reference: 1044361

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H22ClNO	F(000) = 696
Mr = 327.84	Dx = 1.238 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4353 reflections
a = 8.7146 (3) Å	θ = 2.1–28.2°
b = 12.3963 (4) Å	µ = 0.22 mm−1
c = 16.6117 (6) Å	T = 293 K
β = 101.523 (2)°	Block, colourless
V = 1758.37 (10) Å3	0.25 × 0.23 × 0.23 mm
Z = 4

Bruker APEXII CCD diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.946, Tmax = 0.950	k = −16→14
16473 measured reflections	l = −22→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
4353 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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
C17	0.6269 (2)	0.82630 (15)	0.42412 (12)	0.0533 (5)
H17	0.6507	0.8995	0.4264	0.064*
C1	0.3083 (2)	0.97610 (15)	0.30256 (11)	0.0498 (4)
C2	0.2026 (2)	0.88094 (17)	0.31112 (13)	0.0579 (5)
H2A	0.1400	0.8972	0.3517	0.069*
H2B	0.2657	0.8177	0.3293	0.069*
C3	0.4639 (5)	1.0949 (3)	0.11267 (17)	0.1078 (11)
H3A	0.4508	1.1680	0.1290	0.162*
H3B	0.3657	1.0575	0.1062	0.162*
H3C	0.4991	1.0943	0.0615	0.162*
C4	0.53945 (19)	1.05108 (12)	0.26296 (10)	0.0426 (4)
H4	0.4660	1.1118	0.2571	0.051*
C5	0.67052 (19)	1.08102 (12)	0.33476 (10)	0.0415 (4)
C6	0.6292 (2)	1.13399 (16)	0.40066 (12)	0.0548 (5)
H6	0.5240	1.1470	0.4003	0.066*
C7	0.7409 (3)	1.16786 (19)	0.46692 (14)	0.0678 (6)
H7	0.7102	1.2039	0.5102	0.081*
C8	0.8963 (3)	1.14864 (17)	0.46926 (15)	0.0674 (6)
H8	0.9713	1.1707	0.5142	0.081*
C9	0.9404 (2)	1.09646 (16)	0.40468 (14)	0.0615 (5)
H9	1.0458	1.0829	0.4061	0.074*
C10	0.8292 (2)	1.06365 (14)	0.33729 (12)	0.0507 (4)
H10	0.8610	1.0297	0.2934	0.061*
C12	0.5843 (2)	1.03897 (16)	0.17806 (11)	0.0548 (5)
H12	0.6843	1.0764	0.1807	0.066*
C13	0.6075 (3)	0.92372 (16)	0.15453 (13)	0.0677 (6)
H13A	0.5134	0.8986	0.1178	0.081*
H13B	0.6929	0.9205	0.1250	0.081*
C14	0.6440 (3)	0.84909 (14)	0.22878 (13)	0.0555 (5)
H14A	0.7360	0.8750	0.2666	0.067*
H14B	0.6661	0.7772	0.2111	0.067*
C15	0.5053 (2)	0.84491 (12)	0.27212 (11)	0.0446 (4)
H15	0.4208	0.8059	0.2360	0.053*
C16	0.54725 (18)	0.78122 (13)	0.35133 (10)	0.0439 (4)
C18	0.6713 (2)	0.76237 (18)	0.49382 (13)	0.0601 (5)
H18	0.7253	0.7932	0.5423	0.072*
C19	0.6364 (3)	0.65523 (18)	0.49162 (15)	0.0633 (5)
H19	0.6673	0.6130	0.5383	0.076*
C20	0.5549 (3)	0.60920 (16)	0.41981 (15)	0.0660 (6)
H20	0.5300	0.5362	0.4184	0.079*
C21	0.5101 (2)	0.67207 (14)	0.34978 (13)	0.0533 (5)
H21	0.4551	0.6410	0.3016	0.064*
N1	0.44797 (15)	0.95570 (11)	0.28196 (8)	0.0429 (4)
O1	0.25929 (16)	1.06617 (12)	0.31359 (10)	0.0666 (4)
Cl1	0.07878 (7)	0.85512 (5)	0.21470 (4)	0.0825 (3)

	U11	U22	U33	U12	U13	U23
C17	0.0562 (11)	0.0472 (10)	0.0536 (11)	−0.0082 (8)	0.0041 (8)	0.0001 (8)
C1	0.0431 (9)	0.0574 (10)	0.0479 (9)	0.0011 (7)	0.0069 (7)	0.0009 (8)
C2	0.0448 (9)	0.0684 (12)	0.0604 (12)	−0.0021 (8)	0.0106 (8)	0.0106 (9)
C3	0.156 (3)	0.112 (2)	0.0510 (14)	0.046 (2)	0.0100 (16)	0.0171 (14)
C4	0.0463 (8)	0.0389 (8)	0.0431 (9)	0.0000 (6)	0.0101 (7)	0.0021 (6)
C5	0.0471 (8)	0.0327 (7)	0.0455 (9)	−0.0017 (6)	0.0110 (7)	0.0004 (6)
C6	0.0509 (10)	0.0632 (11)	0.0518 (11)	0.0061 (8)	0.0138 (8)	−0.0084 (8)
C7	0.0716 (14)	0.0793 (14)	0.0506 (11)	0.0073 (11)	0.0079 (10)	−0.0165 (10)
C8	0.0613 (12)	0.0715 (13)	0.0623 (13)	−0.0037 (10)	−0.0046 (10)	−0.0086 (10)
C9	0.0477 (10)	0.0570 (11)	0.0772 (14)	−0.0019 (8)	0.0062 (9)	−0.0096 (10)
C10	0.0494 (9)	0.0437 (9)	0.0601 (11)	−0.0015 (7)	0.0139 (8)	−0.0070 (8)
C12	0.0668 (12)	0.0546 (11)	0.0447 (10)	−0.0038 (8)	0.0151 (8)	0.0025 (8)
C13	0.0993 (16)	0.0601 (12)	0.0502 (11)	0.0033 (11)	0.0305 (11)	−0.0054 (9)
C14	0.0698 (12)	0.0449 (9)	0.0578 (11)	0.0054 (8)	0.0269 (9)	−0.0036 (8)
C15	0.0472 (9)	0.0385 (8)	0.0465 (9)	−0.0035 (6)	0.0057 (7)	−0.0045 (6)
C16	0.0395 (8)	0.0427 (8)	0.0496 (9)	−0.0013 (6)	0.0089 (7)	−0.0017 (7)
C18	0.0521 (10)	0.0715 (13)	0.0528 (11)	−0.0055 (9)	0.0014 (8)	0.0043 (9)
C19	0.0608 (12)	0.0658 (12)	0.0648 (13)	0.0057 (9)	0.0159 (10)	0.0212 (10)
C20	0.0820 (15)	0.0449 (10)	0.0749 (14)	−0.0032 (9)	0.0245 (12)	0.0103 (9)
C21	0.0600 (11)	0.0424 (9)	0.0580 (11)	−0.0060 (7)	0.0134 (9)	−0.0014 (8)
N1	0.0422 (7)	0.0418 (7)	0.0445 (8)	−0.0020 (5)	0.0081 (6)	0.0003 (6)
O1	0.0523 (8)	0.0640 (9)	0.0863 (11)	0.0095 (6)	0.0205 (7)	−0.0041 (7)
Cl1	0.0729 (4)	0.0820 (5)	0.0812 (5)	−0.0188 (3)	−0.0121 (3)	−0.0008 (3)

C17—C16	1.386 (2)	C8—H8	0.9300
C17—C18	1.393 (3)	C9—C10	1.387 (3)
C17—H17	0.9300	C9—H9	0.9300
C1—O1	1.222 (2)	C10—H10	0.9300
C1—N1	1.352 (2)	C12—C13	1.505 (3)
C1—C2	1.521 (3)	C12—H12	0.9800
C2—Cl1	1.773 (2)	C13—C14	1.524 (3)
C2—H2A	0.9700	C13—H13A	0.9700
C2—H2B	0.9700	C13—H13B	0.9700
C3—C12	1.518 (3)	C14—C15	1.526 (3)
C3—H3A	0.9600	C14—H14A	0.9700
C3—H3B	0.9600	C14—H14B	0.9700
C3—H3C	0.9600	C15—N1	1.482 (2)
C4—N1	1.495 (2)	C15—C16	1.515 (2)
C4—C5	1.523 (2)	C15—H15	0.9800
C4—C12	1.544 (2)	C16—C21	1.390 (2)
C4—H4	0.9800	C18—C19	1.361 (3)
C5—C6	1.384 (2)	C18—H18	0.9300
C5—C10	1.392 (2)	C19—C20	1.384 (3)
C6—C7	1.381 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.390 (3)
C7—C8	1.368 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.372 (3)
C16—C17—C18	120.23 (17)	C13—C12—C3	110.9 (2)
C16—C17—H17	119.9	C13—C12—C4	113.64 (15)
C18—C17—H17	119.9	C3—C12—C4	110.11 (19)
O1—C1—N1	124.60 (17)	C13—C12—H12	107.3
O1—C1—C2	117.28 (17)	C3—C12—H12	107.3
N1—C1—C2	118.11 (16)	C4—C12—H12	107.3
C1—C2—Cl1	109.05 (13)	C14—C13—C12	112.53 (17)
C1—C2—H2A	109.9	C14—C13—H13A	109.1
Cl1—C2—H2A	109.9	C12—C13—H13A	109.1
C1—C2—H2B	109.9	C14—C13—H13B	109.1
Cl1—C2—H2B	109.9	C12—C13—H13B	109.1
H2A—C2—H2B	108.3	H13A—C13—H13B	107.8
C12—C3—H3A	109.5	C13—C14—C15	110.24 (17)
C12—C3—H3B	109.5	C13—C14—H14A	109.6
H3A—C3—H3B	109.5	C15—C14—H14A	109.6
C12—C3—H3C	109.5	C13—C14—H14B	109.6
H3A—C3—H3C	109.5	C15—C14—H14B	109.6
H3B—C3—H3C	109.5	H14A—C14—H14B	108.1
N1—C4—C5	112.06 (13)	N1—C15—C16	114.54 (14)
N1—C4—C12	111.04 (13)	N1—C15—C14	109.68 (13)
C5—C4—C12	116.84 (14)	C16—C15—C14	110.55 (15)
N1—C4—H4	105.3	N1—C15—H15	107.2
C5—C4—H4	105.3	C16—C15—H15	107.2
C12—C4—H4	105.3	C14—C15—H15	107.2
C6—C5—C10	117.60 (16)	C17—C16—C21	118.86 (17)
C6—C5—C4	117.51 (15)	C17—C16—C15	122.65 (15)
C10—C5—C4	124.82 (15)	C21—C16—C15	118.43 (15)
C7—C6—C5	121.42 (18)	C19—C18—C17	120.6 (2)
C7—C6—H6	119.3	C19—C18—H18	119.7
C5—C6—H6	119.3	C17—C18—H18	119.7
C8—C7—C6	120.4 (2)	C18—C19—C20	119.92 (19)
C8—C7—H7	119.8	C18—C19—H19	120.0
C6—C7—H7	119.8	C20—C19—H19	120.0
C7—C8—C9	119.4 (2)	C19—C20—C21	120.01 (18)
C7—C8—H8	120.3	C19—C20—H20	120.0
C9—C8—H8	120.3	C21—C20—H20	120.0
C8—C9—C10	120.65 (19)	C20—C21—C16	120.33 (19)
C8—C9—H9	119.7	C20—C21—H21	119.8
C10—C9—H9	119.7	C16—C21—H21	119.8
C5—C10—C9	120.56 (18)	C1—N1—C15	122.79 (14)
C5—C10—H10	119.7	C1—N1—C4	116.78 (14)
C9—C10—H10	119.7	C15—N1—C4	120.28 (13)
O1—C1—C2—Cl1	88.83 (19)	C18—C17—C16—C15	−175.86 (17)
N1—C1—C2—Cl1	−90.01 (18)	N1—C15—C16—C17	−41.6 (2)
N1—C4—C5—C6	−75.98 (19)	C14—C15—C16—C17	82.9 (2)
C12—C4—C5—C6	154.28 (16)	N1—C15—C16—C21	141.29 (16)
N1—C4—C5—C10	107.24 (18)	C14—C15—C16—C21	−94.20 (19)
C12—C4—C5—C10	−22.5 (2)	C16—C17—C18—C19	−0.4 (3)
C10—C5—C6—C7	−0.4 (3)	C17—C18—C19—C20	−0.5 (3)
C4—C5—C6—C7	−177.46 (19)	C18—C19—C20—C21	0.7 (3)
C5—C6—C7—C8	−0.7 (3)	C19—C20—C21—C16	0.2 (3)
C6—C7—C8—C9	0.8 (4)	C17—C16—C21—C20	−1.1 (3)
C7—C8—C9—C10	0.3 (3)	C15—C16—C21—C20	176.11 (18)
C6—C5—C10—C9	1.5 (3)	O1—C1—N1—C15	177.72 (17)
C4—C5—C10—C9	178.23 (16)	C2—C1—N1—C15	−3.5 (3)
C8—C9—C10—C5	−1.4 (3)	O1—C1—N1—C4	−6.8 (3)
N1—C4—C12—C13	−30.7 (2)	C2—C1—N1—C4	171.99 (14)
C5—C4—C12—C13	99.5 (2)	C16—C15—N1—C1	−69.0 (2)
N1—C4—C12—C3	94.4 (2)	C14—C15—N1—C1	166.04 (16)
C5—C4—C12—C3	−135.4 (2)	C16—C15—N1—C4	115.63 (16)
C3—C12—C13—C14	−146.8 (2)	C14—C15—N1—C4	−9.3 (2)
C4—C12—C13—C14	−22.1 (3)	C5—C4—N1—C1	101.09 (17)
C12—C13—C14—C15	63.8 (2)	C12—C4—N1—C1	−126.23 (17)
C13—C14—C15—N1	−46.3 (2)	C5—C4—N1—C15	−83.27 (17)
C13—C14—C15—C16	−173.53 (16)	C12—C4—N1—C15	49.41 (19)
C18—C17—C16—C21	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1	0.93	2.98	3.879 (2)	164
C21—H21···O1i	0.93	2.57	3.472 (3)	165
C14—H14b···Cg1ii	0.98	2.84	3.751 (2)	156

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C5C10 ring.

DHA	DH	HA	D A	DHA
C17H17Cg1	0.93	2.98	3.879(2)	164
C21H21O1i	0.93	2.57	3.472(3)	165
C14H14bCg1ii	0.98	2.84	3.751(2)	156

Symmetry codes: (i) ; (ii) .