2-Chloro-1-(3,3-dimethyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

In the title compound, C21H24ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7 (1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64 (10) and 70.8 (1)°. The mol-ecular structure features short intra-molecular C-H⋯Cl and C-H⋯O contacts. In the crystal, there are no significant inter-molecular inter-actions present.

Related literature

For the synthesis of the title compound, see: Venkatraj et al. (2008 ▶). For the biological activity of piperdine derivatives, see: Ramalingan et al. (2004 ▶), We­intraub et al. (2003 ▶); Ramachandran et al. (2011 ▶). For a related structure, see: Aridoss et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H24ClNO

M = 341.86

Triclinic,

a = 7.5488 (6) Å

b = 9.9706 (7) Å

c = 12.9887 (10) Å

α = 106.783 (4)°

β = 93.022 (4)°

γ = 102.347 (4)°

V = 907.45 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.953, T max = 0.958

13736 measured reflections

3806 independent reflections

3169 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 1.02

3806 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813022289/su2628sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022289/su2628Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022289/su2628Isup3.cml

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

C21H24ClNO	Z = 2
Mr = 341.86	F(000) = 364
Triclinic, P1	Dx = 1.251 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5488 (6) Å	Cell parameters from 3806 reflections
b = 9.9706 (7) Å	θ = 1.7–26.7°
c = 12.9887 (10) Å	µ = 0.22 mm−1
α = 106.783 (4)°	T = 293 K
β = 93.022 (4)°	Block, colourless
γ = 102.347 (4)°	0.22 × 0.20 × 0.20 mm
V = 907.45 (12) Å3

Bruker Kappa APEXII CCD diffractometer	3806 independent reflections
Radiation source: fine-focus sealed tube	3169 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 26.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.953, Tmax = 0.958	k = −12→12
13736 measured reflections	l = −15→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.068P)2 + 0.2438P] where P = (Fo2 + 2Fc2)/3
3806 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.26 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
C1	0.5516 (3)	0.48807 (17)	0.32195 (15)	0.0580 (4)
H1	0.5332	0.5009	0.3941	0.070*
C2	0.5903 (3)	0.6061 (2)	0.2849 (2)	0.0786 (6)
H2	0.5981	0.6977	0.3322	0.094*
C3	0.6172 (3)	0.5900 (2)	0.1796 (2)	0.0799 (7)
H3	0.6462	0.6701	0.1553	0.096*
C4	0.6009 (3)	0.4528 (2)	0.10924 (17)	0.0667 (5)
H4	0.6164	0.4405	0.0368	0.080*
C5	0.5619 (2)	0.33496 (17)	0.14573 (13)	0.0482 (4)
H5	0.5503	0.2432	0.0976	0.058*
C6	0.53966 (19)	0.35088 (14)	0.25340 (11)	0.0391 (3)
C7	0.49478 (19)	0.21737 (14)	0.29103 (11)	0.0368 (3)
H7	0.3659	0.1703	0.2648	0.044*
C8	0.5168 (2)	0.24431 (17)	0.41304 (12)	0.0457 (3)
H8A	0.4581	0.3206	0.4471	0.055*
H8B	0.4553	0.1576	0.4284	0.055*
C9	0.7153 (2)	0.28648 (18)	0.46186 (11)	0.0490 (4)
H9A	0.7209	0.2955	0.5384	0.059*
H9B	0.7728	0.3799	0.4552	0.059*
C10	0.8214 (2)	0.17659 (16)	0.40704 (12)	0.0455 (3)
C11	0.7480 (3)	0.0335 (2)	0.43042 (16)	0.0647 (5)
H11A	0.8242	−0.0315	0.4036	0.097*
H11B	0.6254	−0.0088	0.3951	0.097*
H11C	0.7486	0.0514	0.5071	0.097*
C12	1.0240 (3)	0.2299 (2)	0.45228 (16)	0.0638 (5)
H12A	1.0714	0.3230	0.4439	0.096*
H12B	1.0901	0.1630	0.4136	0.096*
H12C	1.0374	0.2371	0.5277	0.096*
C13	0.79807 (19)	0.14287 (14)	0.28205 (11)	0.0386 (3)
H13	0.8313	0.0504	0.2540	0.046*
C14	0.91734 (19)	0.24389 (16)	0.23129 (12)	0.0424 (3)
C15	0.9668 (2)	0.39355 (18)	0.27324 (15)	0.0541 (4)
H15	0.9322	0.4386	0.3397	0.065*
C16	1.0665 (3)	0.4759 (2)	0.21753 (19)	0.0718 (6)
H16	1.0980	0.5759	0.2464	0.086*
C17	1.1192 (3)	0.4109 (3)	0.1199 (2)	0.0850 (7)
H17	1.1846	0.4669	0.0820	0.102*
C18	1.0757 (3)	0.2639 (3)	0.07813 (18)	0.0800 (7)
H18	1.1131	0.2197	0.0124	0.096*
C19	0.9761 (2)	0.1810 (2)	0.13376 (14)	0.0572 (4)
H19	0.9479	0.0810	0.1051	0.069*
C20	0.5286 (2)	−0.00943 (15)	0.15914 (12)	0.0437 (3)
C21	0.3245 (2)	−0.05018 (19)	0.12339 (14)	0.0570 (4)
H21A	0.2973	−0.1266	0.0546	0.068*
H21B	0.2871	0.0326	0.1129	0.068*
N1	0.60093 (15)	0.11277 (11)	0.24134 (9)	0.0357 (3)
O1	0.62001 (18)	−0.08988 (13)	0.11198 (11)	0.0661 (4)
Cl1	0.19890 (8)	−0.10917 (6)	0.22079 (5)	0.0865 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0763 (12)	0.0397 (8)	0.0540 (10)	0.0194 (8)	0.0015 (8)	0.0055 (7)
C2	0.1003 (17)	0.0380 (9)	0.0930 (16)	0.0173 (9)	−0.0070 (12)	0.0162 (9)
C3	0.0786 (14)	0.0593 (11)	0.1160 (19)	0.0119 (10)	−0.0009 (13)	0.0540 (12)
C4	0.0679 (12)	0.0803 (13)	0.0706 (12)	0.0237 (10)	0.0102 (9)	0.0470 (10)
C5	0.0533 (9)	0.0506 (8)	0.0447 (8)	0.0168 (7)	0.0043 (7)	0.0178 (7)
C6	0.0399 (7)	0.0361 (7)	0.0401 (7)	0.0114 (6)	0.0008 (6)	0.0089 (5)
C7	0.0368 (7)	0.0348 (6)	0.0361 (7)	0.0092 (5)	0.0055 (5)	0.0062 (5)
C8	0.0507 (9)	0.0489 (8)	0.0375 (7)	0.0123 (7)	0.0134 (6)	0.0118 (6)
C9	0.0589 (10)	0.0537 (9)	0.0302 (7)	0.0081 (7)	0.0029 (6)	0.0112 (6)
C10	0.0470 (8)	0.0481 (8)	0.0422 (8)	0.0078 (6)	−0.0021 (6)	0.0189 (6)
C11	0.0736 (12)	0.0623 (10)	0.0682 (11)	0.0131 (9)	0.0026 (9)	0.0388 (9)
C12	0.0537 (10)	0.0718 (11)	0.0631 (11)	0.0091 (9)	−0.0133 (8)	0.0242 (9)
C13	0.0382 (7)	0.0345 (6)	0.0423 (7)	0.0101 (5)	0.0032 (6)	0.0099 (5)
C14	0.0326 (7)	0.0518 (8)	0.0452 (8)	0.0102 (6)	0.0038 (6)	0.0186 (6)
C15	0.0470 (9)	0.0522 (9)	0.0629 (10)	0.0047 (7)	0.0092 (7)	0.0225 (8)
C16	0.0549 (11)	0.0711 (12)	0.0933 (15)	−0.0019 (9)	0.0085 (10)	0.0439 (11)
C17	0.0565 (12)	0.121 (2)	0.0891 (16)	−0.0019 (12)	0.0158 (11)	0.0653 (15)
C18	0.0545 (11)	0.126 (2)	0.0589 (11)	0.0107 (12)	0.0201 (9)	0.0330 (12)
C19	0.0432 (9)	0.0762 (11)	0.0496 (9)	0.0142 (8)	0.0084 (7)	0.0149 (8)
C20	0.0495 (8)	0.0341 (7)	0.0413 (7)	0.0065 (6)	0.0041 (6)	0.0049 (6)
C21	0.0521 (10)	0.0507 (9)	0.0508 (9)	0.0007 (7)	−0.0027 (7)	−0.0011 (7)
N1	0.0376 (6)	0.0304 (5)	0.0363 (6)	0.0075 (4)	0.0030 (5)	0.0067 (4)
O1	0.0637 (8)	0.0485 (6)	0.0685 (8)	0.0174 (6)	0.0048 (6)	−0.0115 (6)
Cl1	0.0704 (4)	0.0732 (4)	0.1052 (5)	−0.0123 (3)	0.0181 (3)	0.0310 (3)

C1—C6	1.381 (2)	C11—H11B	0.9600
C1—C2	1.377 (3)	C11—H11C	0.9600
C1—H1	0.9300	C12—H12A	0.9600
C2—C3	1.361 (3)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.384 (3)	C13—N1	1.4896 (17)
C3—H3	0.9300	C13—C14	1.523 (2)
C4—C5	1.371 (2)	C13—H13	0.9800
C4—H4	0.9300	C14—C19	1.384 (2)
C5—C6	1.385 (2)	C14—C15	1.391 (2)
C5—H5	0.9300	C15—C16	1.378 (3)
C6—C7	1.5252 (19)	C15—H15	0.9300
C7—N1	1.4729 (17)	C16—C17	1.369 (4)
C7—C8	1.5228 (19)	C16—H16	0.9300
C7—H7	0.9800	C17—C18	1.367 (4)
C8—C9	1.517 (2)	C17—H17	0.9300
C8—H8A	0.9700	C18—C19	1.381 (3)
C8—H8B	0.9700	C18—H18	0.9300
C9—C10	1.528 (2)	C19—H19	0.9300
C9—H9A	0.9700	C20—O1	1.2214 (19)
C9—H9B	0.9700	C20—N1	1.3510 (17)
C10—C12	1.531 (2)	C20—C21	1.518 (2)
C10—C11	1.538 (2)	C21—Cl1	1.779 (2)
C10—C13	1.552 (2)	C21—H21A	0.9700
C11—H11A	0.9600	C21—H21B	0.9700
C6—C1—C2	120.83 (18)	C10—C11—H11C	109.5
C6—C1—H1	119.6	H11A—C11—H11C	109.5
C2—C1—H1	119.6	H11B—C11—H11C	109.5
C3—C2—C1	120.67 (18)	C10—C12—H12A	109.5
C3—C2—H2	119.7	C10—C12—H12B	109.5
C1—C2—H2	119.7	H12A—C12—H12B	109.5
C2—C3—C4	119.18 (17)	C10—C12—H12C	109.5
C2—C3—H3	120.4	H12A—C12—H12C	109.5
C4—C3—H3	120.4	H12B—C12—H12C	109.5
C5—C4—C3	120.35 (19)	N1—C13—C14	111.88 (11)
C5—C4—H4	119.8	N1—C13—C10	109.68 (11)
C3—C4—H4	119.8	C14—C13—C10	119.26 (12)
C4—C5—C6	120.80 (16)	N1—C13—H13	104.9
C4—C5—H5	119.6	C14—C13—H13	104.9
C6—C5—H5	119.6	C10—C13—H13	104.9
C1—C6—C5	118.13 (14)	C19—C14—C15	117.72 (16)
C1—C6—C7	122.40 (14)	C19—C14—C13	116.89 (14)
C5—C6—C7	119.42 (12)	C15—C14—C13	125.35 (14)
N1—C7—C8	108.53 (11)	C16—C15—C14	120.80 (18)
N1—C7—C6	111.44 (11)	C16—C15—H15	119.6
C8—C7—C6	116.13 (11)	C14—C15—H15	119.6
N1—C7—H7	106.7	C15—C16—C17	120.2 (2)
C8—C7—H7	106.7	C15—C16—H16	119.9
C6—C7—H7	106.7	C17—C16—H16	119.9
C9—C8—C7	112.77 (12)	C18—C17—C16	120.09 (19)
C9—C8—H8A	109.0	C18—C17—H17	120.0
C7—C8—H8A	109.0	C16—C17—H17	120.0
C9—C8—H8B	109.0	C17—C18—C19	119.9 (2)
C7—C8—H8B	109.0	C17—C18—H18	120.1
H8A—C8—H8B	107.8	C19—C18—H18	120.1
C8—C9—C10	112.41 (12)	C14—C19—C18	121.28 (19)
C8—C9—H9A	109.1	C14—C19—H19	119.4
C10—C9—H9A	109.1	C18—C19—H19	119.4
C8—C9—H9B	109.1	O1—C20—N1	123.03 (14)
C10—C9—H9B	109.1	O1—C20—C21	117.96 (13)
H9A—C9—H9B	107.9	N1—C20—C21	119.00 (13)
C12—C10—C9	110.51 (14)	C20—C21—Cl1	111.42 (12)
C12—C10—C11	107.52 (13)	C20—C21—H21A	109.3
C9—C10—C11	109.57 (14)	Cl1—C21—H21A	109.3
C12—C10—C13	110.43 (14)	C20—C21—H21B	109.3
C9—C10—C13	111.76 (11)	Cl1—C21—H21B	109.3
C11—C10—C13	106.88 (13)	H21A—C21—H21B	108.0
C10—C11—H11A	109.5	C20—N1—C7	123.13 (12)
C10—C11—H11B	109.5	C20—N1—C13	117.91 (11)
H11A—C11—H11B	109.5	C7—N1—C13	118.95 (10)
C6—C1—C2—C3	0.2 (3)	C10—C13—C14—C19	142.88 (14)
C1—C2—C3—C4	1.5 (4)	N1—C13—C14—C15	90.66 (17)
C2—C3—C4—C5	−1.4 (3)	C10—C13—C14—C15	−39.2 (2)
C3—C4—C5—C6	−0.5 (3)	C19—C14—C15—C16	1.8 (2)
C2—C1—C6—C5	−2.0 (3)	C13—C14—C15—C16	−176.05 (15)
C2—C1—C6—C7	−179.24 (17)	C14—C15—C16—C17	−0.4 (3)
C4—C5—C6—C1	2.2 (2)	C15—C16—C17—C18	−1.1 (3)
C4—C5—C6—C7	179.49 (15)	C16—C17—C18—C19	1.0 (3)
C1—C6—C7—N1	−141.81 (15)	C15—C14—C19—C18	−1.9 (2)
C5—C6—C7—N1	41.02 (17)	C13—C14—C19—C18	176.13 (16)
C1—C6—C7—C8	−16.9 (2)	C17—C18—C19—C14	0.6 (3)
C5—C6—C7—C8	165.97 (13)	O1—C20—C21—Cl1	107.89 (16)
N1—C7—C8—C9	52.72 (16)	N1—C20—C21—Cl1	−71.80 (17)
C6—C7—C8—C9	−73.70 (16)	O1—C20—N1—C7	173.64 (14)
C7—C8—C9—C10	−54.77 (17)	C21—C20—N1—C7	−6.7 (2)
C8—C9—C10—C12	175.17 (13)	O1—C20—N1—C13	−5.6 (2)
C8—C9—C10—C11	−66.52 (16)	C21—C20—N1—C13	174.10 (13)
C8—C9—C10—C13	51.76 (17)	C8—C7—N1—C20	126.99 (14)
C12—C10—C13—N1	−171.49 (12)	C6—C7—N1—C20	−103.91 (15)
C9—C10—C13—N1	−48.04 (15)	C8—C7—N1—C13	−53.80 (15)
C11—C10—C13—N1	71.84 (15)	C6—C7—N1—C13	75.29 (14)
C12—C10—C13—C14	−40.64 (18)	C14—C13—N1—C20	96.58 (15)
C9—C10—C13—C14	82.81 (16)	C10—C13—N1—C20	−128.75 (13)
C11—C10—C13—C14	−157.31 (13)	C14—C13—N1—C7	−82.66 (14)
N1—C13—C14—C19	−87.25 (15)	C10—C13—N1—C7	52.00 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1	0.98	2.68	3.3736 (16)	128
C13—H13···O1	0.98	2.27	2.732 (2)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cl1	0.98	2.68	3.3736 (16)	128
C13—H13⋯O1	0.98	2.27	2.732 (2)	108