1-Di-chloro-acetyl-t-3-isopropyl-r-2,c-6-di-phenyl-piperidin-4-one.

In the title compound, C22H23Cl2NO2, the piperidine ring adopts a twist-boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend dihedral angles of 60.6 (2) and 84.2 (1)°, respectively, with the mean plane of the piperidine ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions into zigzag chains running along the c-axis direction.

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ▶); Nalanishi et al. (1974 ▶); Michael (2001 ▶); Pinder (1992 ▶); Rubiralta et al. (1991 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C22H23Cl2NO2

M = 404.31

Orthorhombic,

a = 18.4336 (14) Å

b = 9.4516 (7) Å

c = 11.7077 (9) Å

V = 2039.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.929, T max = 0.941

10509 measured reflections

4437 independent reflections

3882 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.04

4437 reflections

244 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1759 Friedel pairs

Absolute structure parameter: −0.08 (8)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019582/bt6918sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019582/bt6918Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019582/bt6918Isup3.cml

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

C22H23Cl2NO2	F(000) = 848
Mr = 404.31	Dx = 1.317 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3882 reflections
a = 18.4336 (14) Å	θ = 2.2–28.4°
b = 9.4516 (7) Å	µ = 0.34 mm−1
c = 11.7077 (9) Å	T = 293 K
V = 2039.8 (3) Å3	Block, yellow
Z = 4	0.22 × 0.20 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	4437 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→24
Tmin = 0.929, Tmax = 0.941	k = −12→12
10509 measured reflections	l = −11→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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.6068P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4437 reflections	Δρmax = 0.69 e Å−3
244 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 1759 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.08 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.67099 (11)	0.9032 (2)	0.91976 (19)	0.0306 (4)
H2	0.6651	0.9516	0.9932	0.037*
C3	0.70822 (12)	1.0091 (2)	0.8399 (2)	0.0352 (4)
H3	0.7584	1.0209	0.8659	0.042*
C4	0.71030 (13)	0.9535 (3)	0.7191 (2)	0.0421 (5)
C5	0.65663 (14)	0.8387 (2)	0.6894 (2)	0.0414 (5)
H5A	0.6797	0.7479	0.7023	0.050*
H5B	0.6459	0.8452	0.6084	0.050*
C6	0.58452 (12)	0.8409 (2)	0.7551 (2)	0.0333 (4)
H6	0.5536	0.9146	0.7221	0.040*
C7	0.54776 (12)	0.6975 (2)	0.7366 (2)	0.0381 (5)
C8	0.5026 (2)	0.6797 (4)	0.6451 (4)	0.0778 (12)
H8	0.4919	0.7560	0.5979	0.093*
C9	0.4727 (3)	0.5481 (5)	0.6228 (4)	0.0948 (16)
H9	0.4419	0.5374	0.5604	0.114*
C10	0.4871 (2)	0.4346 (4)	0.6897 (3)	0.0685 (9)
H10	0.4683	0.3460	0.6720	0.082*
C11	0.5299 (2)	0.4531 (3)	0.7837 (4)	0.0712 (11)
H11	0.5386	0.3775	0.8327	0.085*
C12	0.56030 (17)	0.5841 (3)	0.8064 (3)	0.0601 (9)
H12	0.5898	0.5951	0.8703	0.072*
C13	0.71354 (11)	0.7680 (2)	0.9446 (2)	0.0348 (5)
C14	0.77614 (13)	0.7293 (3)	0.8883 (3)	0.0464 (6)
H14	0.7927	0.7833	0.8272	0.056*
C15	0.81513 (18)	0.6090 (3)	0.9224 (3)	0.0604 (8)
H15	0.8577	0.5846	0.8845	0.072*
C16	0.79074 (18)	0.5271 (3)	1.0114 (3)	0.0623 (8)
H16	0.8163	0.4467	1.0332	0.075*
C17	0.72847 (17)	0.5646 (3)	1.0682 (3)	0.0567 (7)
H17	0.7120	0.5096	1.1287	0.068*
C18	0.69012 (14)	0.6841 (3)	1.0356 (2)	0.0442 (6)
H18	0.6482	0.7088	1.0750	0.053*
C19	0.67141 (14)	1.1579 (2)	0.8402 (2)	0.0400 (5)
H19	0.6234	1.1489	0.8048	0.048*
C20	0.6614 (2)	1.2139 (3)	0.9603 (3)	0.0606 (8)
H20A	0.6331	1.1479	1.0039	0.091*
H20B	0.6368	1.3033	0.9575	0.091*
H20C	0.7080	1.2259	0.9958	0.091*
C21	0.7155 (2)	1.2637 (3)	0.7707 (3)	0.0675 (9)
H21A	0.7222	1.2280	0.6946	0.101*
H21B	0.7620	1.2774	0.8061	0.101*
H21C	0.6902	1.3523	0.7675	0.101*
C22	0.54042 (12)	0.8987 (2)	0.9506 (2)	0.0383 (5)
C23	0.46416 (13)	0.9023 (3)	0.8997 (3)	0.0506 (7)
H23	0.4622	0.8437	0.8307	0.061*
N1	0.59629 (9)	0.87405 (18)	0.87687 (17)	0.0309 (4)
O1	0.75440 (14)	0.9925 (2)	0.6505 (2)	0.0671 (6)
O2	0.54794 (11)	0.9232 (3)	1.05165 (19)	0.0602 (6)
Cl2	0.44564 (6)	1.08090 (11)	0.86504 (12)	0.0926 (4)
Cl1	0.40029 (5)	0.84201 (14)	1.00044 (13)	0.0960 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0295 (9)	0.0290 (9)	0.0334 (11)	−0.0014 (7)	−0.0020 (7)	−0.0024 (8)
C3	0.0349 (9)	0.0292 (9)	0.0414 (12)	−0.0046 (7)	0.0037 (8)	−0.0004 (9)
C4	0.0450 (11)	0.0359 (11)	0.0454 (14)	0.0003 (9)	0.0145 (10)	0.0012 (10)
C5	0.0476 (12)	0.0440 (12)	0.0325 (12)	0.0004 (10)	0.0069 (9)	−0.0047 (10)
C6	0.0358 (9)	0.0345 (9)	0.0294 (11)	0.0002 (8)	−0.0024 (8)	−0.0015 (9)
C7	0.0363 (10)	0.0391 (11)	0.0389 (13)	−0.0020 (8)	−0.0029 (9)	−0.0037 (9)
C8	0.101 (3)	0.0673 (19)	0.065 (2)	−0.0354 (19)	−0.040 (2)	0.0188 (17)
C9	0.129 (4)	0.082 (2)	0.073 (3)	−0.051 (2)	−0.055 (3)	0.008 (2)
C10	0.077 (2)	0.0510 (15)	0.078 (2)	−0.0206 (15)	−0.0209 (18)	−0.0113 (15)
C11	0.081 (2)	0.0369 (13)	0.096 (3)	−0.0077 (13)	−0.037 (2)	0.0021 (15)
C12	0.0698 (18)	0.0399 (13)	0.070 (2)	−0.0064 (12)	−0.0348 (16)	0.0017 (13)
C13	0.0317 (9)	0.0298 (9)	0.0428 (13)	−0.0032 (7)	−0.0055 (9)	−0.0002 (9)
C14	0.0407 (11)	0.0413 (12)	0.0572 (17)	0.0038 (9)	0.0013 (11)	0.0002 (12)
C15	0.0531 (15)	0.0546 (15)	0.073 (2)	0.0193 (13)	−0.0017 (14)	−0.0057 (15)
C16	0.0674 (18)	0.0362 (12)	0.083 (2)	0.0118 (12)	−0.0197 (17)	0.0005 (14)
C17	0.0659 (17)	0.0392 (13)	0.0649 (19)	−0.0080 (11)	−0.0152 (14)	0.0113 (13)
C18	0.0427 (11)	0.0381 (11)	0.0517 (16)	−0.0034 (9)	−0.0032 (11)	0.0042 (11)
C19	0.0457 (12)	0.0291 (10)	0.0451 (14)	−0.0003 (8)	−0.0019 (10)	0.0012 (9)
C20	0.094 (2)	0.0332 (12)	0.0545 (18)	0.0094 (13)	0.0004 (16)	−0.0070 (12)
C21	0.094 (2)	0.0342 (13)	0.074 (2)	−0.0049 (13)	0.0195 (19)	0.0127 (14)
C22	0.0305 (10)	0.0411 (11)	0.0433 (14)	−0.0007 (8)	0.0053 (9)	−0.0033 (10)
C23	0.0322 (11)	0.0550 (14)	0.065 (2)	0.0027 (10)	0.0052 (11)	−0.0120 (13)
N1	0.0275 (7)	0.0332 (8)	0.0319 (10)	−0.0009 (6)	0.0007 (7)	−0.0015 (7)
O1	0.0794 (14)	0.0592 (11)	0.0628 (14)	−0.0189 (11)	0.0378 (12)	−0.0073 (10)
O2	0.0470 (10)	0.0915 (16)	0.0422 (12)	−0.0024 (10)	0.0119 (8)	−0.0122 (10)
Cl2	0.0772 (6)	0.0778 (6)	0.1229 (10)	0.0262 (5)	−0.0136 (6)	0.0178 (6)
Cl1	0.0470 (4)	0.1175 (8)	0.1233 (10)	−0.0192 (5)	0.0235 (5)	0.0129 (7)

C2—N1	1.491 (2)	C13—C14	1.378 (3)
C2—C13	1.527 (3)	C13—C18	1.396 (4)
C2—C3	1.532 (3)	C14—C15	1.403 (4)
C2—H2	0.9800	C14—H14	0.9300
C3—C4	1.509 (4)	C15—C16	1.374 (5)
C3—C19	1.562 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—C17	1.373 (5)
C4—O1	1.200 (3)	C16—H16	0.9300
C4—C5	1.509 (3)	C17—C18	1.386 (4)
C5—C6	1.536 (3)	C17—H17	0.9300
C5—H5A	0.9700	C18—H18	0.9300
C5—H5B	0.9700	C19—C20	1.514 (4)
C6—N1	1.476 (3)	C19—C21	1.524 (4)
C6—C7	1.531 (3)	C19—H19	0.9800
C6—H6	0.9800	C20—H20A	0.9600
C7—C8	1.367 (4)	C20—H20B	0.9600
C7—C12	1.368 (4)	C20—H20C	0.9600
C8—C9	1.386 (5)	C21—H21A	0.9600
C8—H8	0.9300	C21—H21B	0.9600
C9—C10	1.354 (6)	C21—H21C	0.9600
C9—H9	0.9300	C22—O2	1.213 (3)
C10—C11	1.365 (5)	C22—N1	1.364 (3)
C10—H10	0.9300	C22—C23	1.527 (3)
C11—C12	1.385 (4)	C23—Cl1	1.762 (3)
C11—H11	0.9300	C23—Cl2	1.769 (3)
C12—H12	0.9300	C23—H23	0.9800
N1—C2—C13	112.56 (16)	C18—C13—C2	117.5 (2)
N1—C2—C3	109.19 (18)	C13—C14—C15	120.5 (3)
C13—C2—C3	115.65 (18)	C13—C14—H14	119.7
N1—C2—H2	106.3	C15—C14—H14	119.7
C13—C2—H2	106.3	C16—C15—C14	120.3 (3)
C3—C2—H2	106.3	C16—C15—H15	119.8
C4—C3—C2	110.86 (18)	C14—C15—H15	119.8
C4—C3—C19	109.1 (2)	C17—C16—C15	119.7 (3)
C2—C3—C19	113.09 (18)	C17—C16—H16	120.2
C4—C3—H3	107.9	C15—C16—H16	120.2
C2—C3—H3	107.9	C16—C17—C18	120.3 (3)
C19—C3—H3	107.9	C16—C17—H17	119.9
O1—C4—C3	122.5 (2)	C18—C17—H17	119.9
O1—C4—C5	120.7 (2)	C17—C18—C13	121.0 (3)
C3—C4—C5	116.7 (2)	C17—C18—H18	119.5
C4—C5—C6	116.24 (19)	C13—C18—H18	119.5
C4—C5—H5A	108.2	C20—C19—C21	109.4 (2)
C6—C5—H5A	108.2	C20—C19—C3	111.7 (2)
C4—C5—H5B	108.2	C21—C19—C3	111.0 (2)
C6—C5—H5B	108.2	C20—C19—H19	108.2
H5A—C5—H5B	107.4	C21—C19—H19	108.2
N1—C6—C7	112.94 (19)	C3—C19—H19	108.2
N1—C6—C5	111.08 (18)	C19—C20—H20A	109.5
C7—C6—C5	107.48 (18)	C19—C20—H20B	109.5
N1—C6—H6	108.4	H20A—C20—H20B	109.5
C7—C6—H6	108.4	C19—C20—H20C	109.5
C5—C6—H6	108.4	H20A—C20—H20C	109.5
C8—C7—C12	118.4 (2)	H20B—C20—H20C	109.5
C8—C7—C6	119.3 (2)	C19—C21—H21A	109.5
C12—C7—C6	122.3 (2)	C19—C21—H21B	109.5
C7—C8—C9	120.0 (3)	H21A—C21—H21B	109.5
C7—C8—H8	120.0	C19—C21—H21C	109.5
C9—C8—H8	120.0	H21A—C21—H21C	109.5
C10—C9—C8	121.6 (3)	H21B—C21—H21C	109.5
C10—C9—H9	119.2	O2—C22—N1	124.3 (2)
C8—C9—H9	119.2	O2—C22—C23	118.8 (2)
C9—C10—C11	118.6 (3)	N1—C22—C23	116.9 (2)
C9—C10—H10	120.7	C22—C23—Cl1	110.3 (2)
C11—C10—H10	120.7	C22—C23—Cl2	106.77 (18)
C10—C11—C12	120.2 (3)	Cl1—C23—Cl2	109.47 (15)
C10—C11—H11	119.9	C22—C23—H23	110.1
C12—C11—H11	119.9	Cl1—C23—H23	110.1
C7—C12—C11	121.1 (3)	Cl2—C23—H23	110.1
C7—C12—H12	119.4	C22—N1—C6	122.46 (18)
C11—C12—H12	119.4	C22—N1—C2	116.91 (19)
C14—C13—C18	118.2 (2)	C6—N1—C2	120.02 (17)
C14—C13—C2	124.1 (2)
N1—C2—C3—C4	−57.6 (2)	C18—C13—C14—C15	−0.3 (4)
C13—C2—C3—C4	70.6 (2)	C2—C13—C14—C15	174.9 (3)
N1—C2—C3—C19	65.3 (2)	C13—C14—C15—C16	0.9 (5)
C13—C2—C3—C19	−166.52 (19)	C14—C15—C16—C17	−0.9 (5)
C2—C3—C4—O1	−156.1 (3)	C15—C16—C17—C18	0.3 (5)
C19—C3—C4—O1	78.7 (3)	C16—C17—C18—C13	0.4 (4)
C2—C3—C4—C5	20.3 (3)	C14—C13—C18—C17	−0.4 (4)
C19—C3—C4—C5	−104.8 (2)	C2—C13—C18—C17	−175.9 (2)
O1—C4—C5—C6	−153.7 (3)	C4—C3—C19—C20	174.8 (2)
C3—C4—C5—C6	29.8 (3)	C2—C3—C19—C20	50.9 (3)
C4—C5—C6—N1	−41.1 (3)	C4—C3—C19—C21	−62.9 (3)
C4—C5—C6—C7	−165.1 (2)	C2—C3—C19—C21	173.3 (2)
N1—C6—C7—C8	148.1 (3)	O2—C22—C23—Cl1	−34.0 (3)
C5—C6—C7—C8	−89.1 (3)	N1—C22—C23—Cl1	148.94 (19)
N1—C6—C7—C12	−34.1 (3)	O2—C22—C23—Cl2	84.8 (3)
C5—C6—C7—C12	88.7 (3)	N1—C22—C23—Cl2	−92.2 (2)
C12—C7—C8—C9	−2.2 (6)	O2—C22—N1—C6	178.3 (2)
C6—C7—C8—C9	175.7 (4)	C23—C22—N1—C6	−4.8 (3)
C7—C8—C9—C10	−0.1 (8)	O2—C22—N1—C2	−10.7 (4)
C8—C9—C10—C11	2.7 (8)	C23—C22—N1—C2	166.21 (19)
C9—C10—C11—C12	−2.9 (7)	C7—C6—N1—C22	−67.1 (3)
C8—C7—C12—C11	1.9 (5)	C5—C6—N1—C22	172.1 (2)
C6—C7—C12—C11	−175.9 (3)	C7—C6—N1—C2	122.20 (19)
C10—C11—C12—C7	0.7 (6)	C5—C6—N1—C2	1.4 (3)
N1—C2—C13—C14	117.0 (2)	C13—C2—N1—C22	106.7 (2)
C3—C2—C13—C14	−9.4 (3)	C3—C2—N1—C22	−123.5 (2)
N1—C2—C13—C18	−67.7 (3)	C13—C2—N1—C6	−82.1 (2)
C3—C2—C13—C18	165.8 (2)	C3—C2—N1—C6	47.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.98	2.39	3.144 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.39	3.144 (3)	133

Symmetry code: (i) .