1-Chloro-acetyl-3-isopropyl-r-2,c-6-diphenyl-piperidin-4-one.

In the title compound, C(22)H(24)ClNO(2), the piperidine ring adopts a distorted boat conformation. The dihedral angle between the two phenyl rings is 83.2 (1)°. In the crystal, the mol-ecules are linked into chains running along the b axis by C-H⋯O hydrogen bonds. The Cl atom of the chloro-acetyl group is disordered over two positions with occupancies of 0.66 (2) and 0.34 (2).

Related literature

For general background to piperidine derivatives, see: El-Subbagh et al. (2000 ▶); Jerom & Spencer (1988 ▶); Perumal et al. (2001 ▶); Hagenbach & Gysin (1952 ▶); Mobio et al. (1989 ▶); Katritzky & Fan (1990 ▶); Ganellin & Spickett (1965 ▶). For asymmetry and puckering parameters, see: Nardelli (1983 ▶); Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the synthesis, see: Venkatraj et al. (2008 ▶).

Experimental

Crystal data

C22H24ClNO2

M = 369.87

Monoclinic,

a = 10.3415 (12) Å

b = 9.0243 (9) Å

c = 21.438 (2) Å

β = 90.894 (3)°

V = 2000.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.954, T max = 0.960

19037 measured reflections

4965 independent reflections

3634 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.05

4965 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.24 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, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905497X/ci2993sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905497X/ci2993Isup2.hkl

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

C22H24ClNO2	F(000) = 784
Mr = 369.87	Dx = 1.228 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2052 reflections
a = 10.3415 (12) Å	θ = 1.9–28.3°
b = 9.0243 (9) Å	µ = 0.21 mm−1
c = 21.438 (2) Å	T = 293 K
β = 90.894 (3)°	Block, colourless
V = 2000.5 (4) Å3	0.23 × 0.23 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	4965 independent reflections
Radiation source: fine-focus sealed tube	3634 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.954, Tmax = 0.960	k = −11→12
19037 measured reflections	l = −28→26

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.073P)2 + 0.4534P] where P = (Fo2 + 2Fc2)/3
4965 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.24 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	Occ. (<1)
Cl1A	0.4290 (5)	0.2714 (5)	0.19072 (9)	0.0742 (9)	0.662 (18)
Cl1B	0.4685 (12)	0.2335 (12)	0.2045 (7)	0.097 (2)	0.338 (18)
O1	0.28951 (14)	0.09562 (14)	0.28351 (6)	0.0649 (4)
O2	−0.07198 (13)	0.48645 (19)	0.43316 (7)	0.0758 (5)
N1	0.23607 (12)	0.28293 (14)	0.34870 (6)	0.0385 (3)
C2	0.13248 (14)	0.19074 (18)	0.37710 (7)	0.0416 (3)
H2	0.1191	0.1067	0.3488	0.050*
C3	0.00443 (15)	0.2766 (2)	0.37661 (7)	0.0460 (4)
H3	−0.0585	0.2166	0.3992	0.055*
C4	0.01886 (16)	0.4218 (2)	0.41130 (7)	0.0494 (4)
C5	0.15466 (15)	0.47860 (19)	0.41923 (7)	0.0446 (4)
H5A	0.1910	0.4381	0.4576	0.053*
H5B	0.1513	0.5854	0.4240	0.053*
C6	0.24626 (14)	0.44202 (17)	0.36585 (7)	0.0382 (3)
H6	0.2197	0.5009	0.3294	0.046*
C7	0.30043 (16)	0.22482 (18)	0.29965 (7)	0.0444 (4)
C8	0.39016 (18)	0.3296 (2)	0.26547 (8)	0.0524 (4)
H8A	0.4694	0.3406	0.2898	0.063*	0.662 (18)
H8B	0.3495	0.4263	0.2627	0.063*	0.662 (18)
H8C	0.3412	0.4109	0.2485	0.063*	0.338 (18)
H8D	0.4536	0.3690	0.2941	0.063*	0.338 (18)
C9	0.17615 (15)	0.12393 (18)	0.43941 (7)	0.0447 (4)
C10	0.2790 (2)	0.0264 (2)	0.43950 (10)	0.0638 (5)
H10	0.3203	0.0062	0.4022	0.077*
C11	0.3221 (2)	−0.0420 (3)	0.49375 (12)	0.0769 (6)
H11	0.3916	−0.1073	0.4927	0.092*
C12	0.2619 (2)	−0.0130 (3)	0.54915 (10)	0.0709 (6)
H12	0.2906	−0.0582	0.5858	0.085*
C13	0.1599 (2)	0.0821 (2)	0.55003 (9)	0.0656 (5)
H13	0.1190	0.1015	0.5875	0.079*
C14	0.11594 (18)	0.1510 (2)	0.49564 (8)	0.0541 (4)
H14	0.0459	0.2154	0.4970	0.065*
C15	−0.05025 (19)	0.2994 (3)	0.30908 (9)	0.0619 (5)
H15	0.0186	0.3409	0.2835	0.074*
C16	−0.0902 (4)	0.1544 (3)	0.28166 (14)	0.1154 (12)
H16A	−0.0205	0.0847	0.2860	0.173*
H16B	−0.1114	0.1673	0.2382	0.173*
H16C	−0.1645	0.1177	0.3031	0.173*
C17	−0.1643 (3)	0.4015 (4)	0.30539 (14)	0.1232 (13)
H17A	−0.1407	0.4963	0.3223	0.185*
H17B	−0.2340	0.3606	0.3289	0.185*
H17C	−0.1912	0.4129	0.2626	0.185*
C18	0.38149 (15)	0.49029 (18)	0.38534 (7)	0.0409 (3)
C19	0.41717 (19)	0.6350 (2)	0.37469 (9)	0.0560 (4)
H19	0.3597	0.6991	0.3546	0.067*
C20	0.5382 (2)	0.6861 (2)	0.39369 (10)	0.0674 (5)
H20	0.5611	0.7842	0.3866	0.081*
C21	0.62369 (19)	0.5928 (3)	0.42275 (10)	0.0656 (5)
H21	0.7050	0.6270	0.4351	0.079*
C22	0.58976 (18)	0.4492 (3)	0.43370 (9)	0.0631 (5)
H22	0.6483	0.3856	0.4533	0.076*
C23	0.46858 (17)	0.3976 (2)	0.41585 (8)	0.0511 (4)
H23	0.4455	0.3002	0.4244	0.061*

	U11	U22	U33	U12	U13	U23
Cl1A	0.1037 (17)	0.0687 (12)	0.0512 (8)	−0.0259 (10)	0.0369 (7)	−0.0192 (6)
Cl1B	0.104 (4)	0.077 (3)	0.112 (4)	−0.017 (3)	0.069 (3)	−0.030 (3)
O1	0.0795 (9)	0.0486 (7)	0.0674 (8)	−0.0137 (7)	0.0272 (7)	−0.0207 (6)
O2	0.0458 (7)	0.0976 (12)	0.0841 (10)	0.0165 (7)	0.0073 (7)	−0.0291 (9)
N1	0.0384 (6)	0.0373 (7)	0.0400 (6)	−0.0036 (5)	0.0062 (5)	−0.0048 (5)
C2	0.0383 (7)	0.0427 (8)	0.0440 (7)	−0.0064 (6)	0.0049 (6)	−0.0035 (6)
C3	0.0362 (8)	0.0569 (10)	0.0450 (8)	−0.0049 (7)	0.0034 (6)	−0.0001 (7)
C4	0.0422 (8)	0.0618 (11)	0.0444 (8)	0.0076 (8)	0.0042 (6)	−0.0040 (7)
C5	0.0448 (8)	0.0450 (9)	0.0441 (8)	0.0029 (7)	0.0059 (6)	−0.0079 (7)
C6	0.0395 (7)	0.0365 (8)	0.0388 (7)	0.0011 (6)	0.0025 (5)	−0.0034 (6)
C7	0.0463 (8)	0.0448 (9)	0.0424 (7)	−0.0033 (7)	0.0075 (6)	−0.0065 (6)
C8	0.0616 (10)	0.0507 (10)	0.0456 (8)	−0.0037 (8)	0.0173 (7)	−0.0050 (7)
C9	0.0424 (8)	0.0418 (9)	0.0500 (8)	−0.0109 (7)	0.0046 (6)	0.0026 (7)
C10	0.0636 (12)	0.0599 (12)	0.0682 (12)	0.0076 (10)	0.0117 (9)	0.0112 (9)
C11	0.0686 (13)	0.0721 (15)	0.0902 (16)	0.0093 (11)	0.0031 (11)	0.0279 (12)
C12	0.0746 (14)	0.0682 (13)	0.0694 (12)	−0.0138 (11)	−0.0121 (10)	0.0241 (10)
C13	0.0776 (14)	0.0677 (13)	0.0516 (10)	−0.0166 (11)	0.0048 (9)	0.0084 (9)
C14	0.0557 (10)	0.0535 (10)	0.0531 (9)	−0.0055 (8)	0.0062 (7)	0.0021 (8)
C15	0.0524 (10)	0.0820 (14)	0.0510 (9)	−0.0004 (10)	−0.0046 (8)	0.0034 (9)
C16	0.156 (3)	0.101 (2)	0.0880 (17)	0.026 (2)	−0.0594 (19)	−0.0347 (16)
C17	0.136 (3)	0.129 (3)	0.103 (2)	0.055 (2)	−0.057 (2)	−0.0268 (19)
C18	0.0414 (8)	0.0422 (8)	0.0393 (7)	−0.0018 (7)	0.0064 (6)	−0.0080 (6)
C19	0.0563 (10)	0.0439 (10)	0.0676 (11)	−0.0045 (8)	0.0000 (8)	−0.0062 (8)
C20	0.0657 (12)	0.0539 (11)	0.0829 (14)	−0.0205 (10)	0.0043 (10)	−0.0130 (10)
C21	0.0461 (10)	0.0804 (15)	0.0703 (12)	−0.0131 (10)	−0.0001 (8)	−0.0182 (11)
C22	0.0493 (10)	0.0743 (14)	0.0653 (11)	0.0028 (10)	−0.0079 (8)	−0.0049 (10)
C23	0.0477 (9)	0.0512 (10)	0.0542 (9)	0.0002 (8)	−0.0012 (7)	−0.0005 (7)

Cl1A—C8	1.739 (3)	C10—H10	0.93
Cl1B—C8	1.774 (5)	C11—C12	1.375 (3)
O1—C7	1.221 (2)	C11—H11	0.93
O2—C4	1.207 (2)	C12—C13	1.360 (3)
N1—C7	1.3585 (19)	C12—H12	0.93
N1—C6	1.4853 (19)	C13—C14	1.391 (3)
N1—C2	1.4936 (19)	C13—H13	0.93
C2—C9	1.527 (2)	C14—H14	0.93
C2—C3	1.534 (2)	C15—C16	1.491 (3)
C2—H2	0.98	C15—C17	1.497 (3)
C3—C4	1.513 (2)	C15—H15	0.98
C3—C15	1.560 (2)	C16—H16A	0.96
C3—H3	0.98	C16—H16B	0.96
C4—O2	1.207 (2)	C16—H16C	0.96
C4—C5	1.502 (2)	C17—H17A	0.96
C5—C6	1.533 (2)	C17—H17B	0.96
C5—H5A	0.97	C17—H17C	0.96
C5—H5B	0.97	C18—C19	1.377 (2)
C6—C18	1.517 (2)	C18—C23	1.386 (2)
C6—H6	0.98	C19—C20	1.389 (3)
C7—C8	1.521 (2)	C19—H19	0.93
C8—H8A	0.97	C20—C21	1.364 (3)
C8—H8B	0.97	C20—H20	0.93
C8—H8C	0.96	C21—C22	1.363 (3)
C8—H8D	0.96	C21—H21	0.93
C9—C10	1.381 (3)	C22—C23	1.385 (3)
C9—C14	1.387 (2)	C22—H22	0.93
C10—C11	1.384 (3)	C23—H23	0.93
C7—N1—C6	122.07 (13)	C14—C9—C2	124.06 (16)
C7—N1—C2	117.63 (13)	C9—C10—C11	121.5 (2)
C6—N1—C2	119.08 (12)	C9—C10—H10	119.2
N1—C2—C9	111.86 (12)	C11—C10—H10	119.2
N1—C2—C3	109.90 (13)	C12—C11—C10	119.8 (2)
C9—C2—C3	116.66 (13)	C12—C11—H11	120.1
N1—C2—H2	105.9	C10—C11—H11	120.1
C9—C2—H2	105.9	C13—C12—C11	119.58 (19)
C3—C2—H2	105.9	C13—C12—H12	120.2
C4—C3—C2	110.82 (13)	C11—C12—H12	120.2
C4—C3—C15	111.93 (15)	C12—C13—C14	120.90 (19)
C2—C3—C15	111.93 (14)	C12—C13—H13	119.5
C4—C3—H3	107.3	C14—C13—H13	119.5
C2—C3—H3	107.3	C9—C14—C13	120.30 (19)
C15—C3—H3	107.3	C9—C14—H14	119.8
O2—C4—C5	121.54 (17)	C13—C14—H14	119.8
O2—C4—C3	122.57 (16)	C16—C15—C17	107.8 (2)
C5—C4—C3	115.86 (14)	C16—C15—C3	110.14 (19)
C4—C5—C6	115.44 (13)	C17—C15—C3	113.83 (18)
C4—C5—H5A	108.4	C16—C15—H15	108.3
C6—C5—H5A	108.4	C17—C15—H15	108.3
C4—C5—H5B	108.4	C3—C15—H15	108.3
C6—C5—H5B	108.4	C15—C16—H16A	109.5
H5A—C5—H5B	107.5	C15—C16—H16B	109.5
N1—C6—C18	114.04 (12)	H16A—C16—H16B	109.5
N1—C6—C5	110.53 (12)	C15—C16—H16C	109.5
C18—C6—C5	108.07 (12)	H16A—C16—H16C	109.5
N1—C6—H6	108.0	H16B—C16—H16C	109.5
C18—C6—H6	108.0	C15—C17—H17A	109.5
C5—C6—H6	108.0	C15—C17—H17B	109.5
O1—C7—N1	122.93 (15)	H17A—C17—H17B	109.5
O1—C7—C8	120.78 (14)	C15—C17—H17C	109.5
N1—C7—C8	116.28 (14)	H17A—C17—H17C	109.5
C7—C8—Cl1A	114.03 (15)	H17B—C17—H17C	109.5
C7—C8—Cl1B	109.9 (3)	C19—C18—C23	118.48 (16)
C7—C8—H8A	108.7	C19—C18—C6	118.35 (15)
Cl1A—C8—H8A	108.7	C23—C18—C6	123.11 (15)
Cl1B—C8—H8A	93.1	C18—C19—C20	120.57 (19)
C7—C8—H8B	108.7	C18—C19—H19	119.7
Cl1A—C8—H8B	108.7	C20—C19—H19	119.7
Cl1B—C8—H8B	126.7	C21—C20—C19	120.3 (2)
H8A—C8—H8B	107.6	C21—C20—H20	119.9
C7—C8—H8C	109.6	C19—C20—H20	119.9
Cl1A—C8—H8C	90.5	C22—C21—C20	119.88 (18)
Cl1B—C8—H8C	109.7	C22—C21—H21	120.1
H8A—C8—H8C	124.2	C20—C21—H21	120.1
C7—C8—H8D	109.7	C21—C22—C23	120.41 (19)
Cl1A—C8—H8D	122.4	C21—C22—H22	119.8
Cl1B—C8—H8D	109.7	C23—C22—H22	119.8
H8B—C8—H8D	89.9	C22—C23—C18	120.39 (18)
H8C—C8—H8D	108.2	C22—C23—H23	119.8
C10—C9—C14	117.86 (16)	C18—C23—H23	119.8
C10—C9—C2	118.04 (15)
C7—N1—C2—C9	104.81 (16)	N1—C2—C9—C10	−62.6 (2)
C6—N1—C2—C9	−87.54 (16)	C3—C2—C9—C10	169.66 (16)
C7—N1—C2—C3	−123.94 (15)	N1—C2—C9—C14	119.83 (17)
C6—N1—C2—C3	43.72 (17)	C3—C2—C9—C14	−7.9 (2)
N1—C2—C3—C4	−57.76 (16)	C14—C9—C10—C11	−0.5 (3)
C9—C2—C3—C4	70.91 (18)	C2—C9—C10—C11	−178.19 (19)
N1—C2—C3—C15	67.97 (17)	C9—C10—C11—C12	0.0 (3)
C9—C2—C3—C15	−163.36 (14)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—O2	−157.42 (17)	C11—C12—C13—C14	−0.2 (3)
C15—C3—C4—O2	76.9 (2)	C10—C9—C14—C13	0.6 (3)
C2—C3—C4—C5	20.3 (2)	C2—C9—C14—C13	178.19 (16)
C15—C3—C4—C5	−105.41 (17)	C12—C13—C14—C9	−0.3 (3)
O2—C4—C5—C6	−149.50 (17)	C4—C3—C15—C16	−167.5 (2)
C3—C4—C5—C6	32.7 (2)	C2—C3—C15—C16	67.4 (2)
C7—N1—C6—C18	−62.87 (18)	C4—C3—C15—C17	−46.3 (3)
C2—N1—C6—C18	130.04 (13)	C2—C3—C15—C17	−171.4 (2)
C7—N1—C6—C5	175.14 (14)	N1—C6—C18—C19	150.61 (14)
C2—N1—C6—C5	8.06 (17)	C5—C6—C18—C19	−86.06 (17)
C4—C5—C6—N1	−47.51 (19)	N1—C6—C18—C23	−32.4 (2)
C4—C5—C6—C18	−172.94 (14)	C5—C6—C18—C23	90.93 (18)
C6—N1—C7—O1	−177.26 (16)	C23—C18—C19—C20	0.6 (3)
C2—N1—C7—O1	−10.0 (2)	C6—C18—C19—C20	177.69 (17)
C6—N1—C7—C8	3.6 (2)	C18—C19—C20—C21	0.5 (3)
C2—N1—C7—C8	170.82 (14)	C19—C20—C21—C22	−0.6 (3)
O1—C7—C8—Cl1A	20.2 (3)	C20—C21—C22—C23	−0.4 (3)
N1—C7—C8—Cl1A	−160.6 (3)	C21—C22—C23—C18	1.5 (3)
O1—C7—C8—Cl1B	−0.7 (7)	C19—C18—C23—C22	−1.6 (3)
N1—C7—C8—Cl1B	178.5 (7)	C6—C18—C23—C22	−178.55 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.98	2.57	3.504 (2)	160
C8—H8C···O1i	0.96	2.25	3.203 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.98	2.57	3.504 (2)	160
C8—H8C⋯O1i	0.96	2.25	3.203 (2)	174

Symmetry code: (i) .