Crystal structure of 1-(2-chloro-acet-yl)-3,3-dimethyl-2,6-di-p-tolyl-piperidin-4-one.

In the title compound, C23H26ClNO2, the piperidin-4-one ring adopts a distorted boat conformation. The two p-tolyl rings are nearly normal to each other, making a dihedral angle of 83.33 (10)°. They are inclined to the mean plane of the piperidine ring by 73.2 (1) and 87.22 (9)°. In the crystal, there are no significant inter-molecular inter-actions present.

Related literature

For some biological properties of piperidones, see: Dimmock et al. (2001 ▸); Perumal et al. (2001 ▸). For the synthesis of the title compound, see: Aridoss et al. (2007 ▸). For further literature on piperidones and the crystal structures of similar compounds, see: Parthiban et al. (2009 ▸); Ravindran et al. (1991 ▸); Krishnakumar & Krishnapillay (1996 ▸).

Experimental

Crystal data

C23H26ClNO2

M = 383.90

Monoclinic,

a = 18.7923 (6) Å

b = 18.8289 (5) Å

c = 11.6689 (3) Å

β = 93.162 (2)°

V = 4122.6 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.931, T max = 0.959

29055 measured reflections

3989 independent reflections

3097 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.03

3989 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); 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, publication_text. DOI: 10.1107/S2056989015002613/su5059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002613/su5059Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002613/su5059Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002613/su5059fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

CCDC reference: 1030980

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

C23H26ClNO2	F(000) = 1632
Mr = 383.90	Dx = 1.237 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8523 reflections
a = 18.7923 (6) Å	θ = 2.3–25.5°
b = 18.8289 (5) Å	µ = 0.20 mm−1
c = 11.6689 (3) Å	T = 296 K
β = 93.162 (2)°	Block, colourless
V = 4122.6 (2) Å3	0.35 × 0.30 × 0.25 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3989 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 25.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −23→22
Tmin = 0.931, Tmax = 0.959	k = −23→23
29055 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0577P)2 + 3.5027P] where P = (Fo2 + 2Fc2)/3
3989 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.22 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	0.99934 (14)	0.15212 (14)	0.4159 (3)	0.0785 (8)
H1A	0.9762	0.1118	0.3802	0.118*
H1B	1.0097	0.1423	0.4959	0.118*
H1C	1.0429	0.1616	0.3795	0.118*
C2	0.95102 (11)	0.21596 (11)	0.40374 (19)	0.0516 (5)
C3	0.97183 (11)	0.28078 (11)	0.44787 (18)	0.0532 (5)
H3	1.0169	0.2854	0.4841	0.064*
C4	0.92751 (10)	0.33922 (10)	0.43974 (17)	0.0466 (5)
H4	0.9431	0.3823	0.4711	0.056*
C5	0.86037 (9)	0.33477 (9)	0.38582 (15)	0.0372 (4)
C6	0.83961 (11)	0.26980 (10)	0.34030 (19)	0.0519 (5)
H6	0.7949	0.2652	0.3029	0.062*
C7	0.88421 (12)	0.21166 (11)	0.3495 (2)	0.0603 (6)
H7	0.8688	0.1685	0.3183	0.072*
C8	0.67209 (9)	0.34288 (10)	0.22260 (15)	0.0399 (4)
C9	0.68688 (10)	0.30852 (12)	0.12166 (17)	0.0501 (5)
H9	0.7118	0.3326	0.0669	0.060*
C10	0.66551 (12)	0.23935 (12)	0.1004 (2)	0.0580 (6)
H10	0.6770	0.2177	0.0322	0.070*
C11	0.62763 (11)	0.20178 (11)	0.1777 (2)	0.0540 (5)
C12	0.61085 (12)	0.23649 (12)	0.27655 (19)	0.0607 (6)
H12	0.5842	0.2129	0.3296	0.073*
C13	0.63251 (11)	0.30541 (12)	0.29906 (18)	0.0529 (5)
H13	0.6203	0.3271	0.3668	0.064*
C14	0.60485 (15)	0.12615 (13)	0.1559 (3)	0.0794 (8)
H14A	0.5792	0.1093	0.2194	0.119*
H14B	0.6462	0.0970	0.1475	0.119*
H14C	0.5747	0.1239	0.0869	0.119*
C15	0.70211 (9)	0.41716 (10)	0.24177 (16)	0.0388 (4)
H15	0.6940	0.4422	0.1686	0.047*
C16	0.66973 (10)	0.46453 (10)	0.33298 (16)	0.0433 (4)
C17	0.68764 (10)	0.43549 (10)	0.45226 (16)	0.0426 (4)
C18	0.75270 (10)	0.38867 (10)	0.46625 (16)	0.0449 (4)
H18A	0.7370	0.3396	0.4611	0.054*
H18B	0.7738	0.3958	0.5432	0.054*
C19	0.81131 (9)	0.39888 (9)	0.38170 (15)	0.0369 (4)
H19	0.8397	0.4402	0.4071	0.044*
C20	0.58947 (11)	0.47386 (14)	0.3074 (2)	0.0619 (6)
H20A	0.5810	0.4923	0.2312	0.093*
H20B	0.5710	0.5064	0.3618	0.093*
H20C	0.5661	0.4288	0.3134	0.093*
C21	0.70482 (13)	0.53857 (11)	0.33111 (19)	0.0565 (5)
H21A	0.6953	0.5600	0.2572	0.085*
H21B	0.7554	0.5339	0.3459	0.085*
H21C	0.6856	0.5680	0.3891	0.085*
C22	0.82141 (10)	0.43472 (10)	0.17806 (16)	0.0419 (4)
C23	0.90131 (10)	0.43746 (11)	0.20559 (18)	0.0494 (5)
H23A	0.9206	0.3897	0.2052	0.059*
H23B	0.9106	0.4570	0.2819	0.059*
N1	0.78074 (7)	0.41404 (8)	0.26376 (12)	0.0364 (3)
O1	0.79731 (8)	0.44923 (10)	0.08186 (12)	0.0640 (4)
O2	0.65195 (8)	0.44814 (8)	0.53268 (12)	0.0578 (4)
Cl1	0.94435 (3)	0.48999 (3)	0.10507 (5)	0.05769 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0700 (16)	0.0599 (15)	0.106 (2)	0.0246 (12)	0.0088 (15)	0.0049 (14)
C2	0.0500 (12)	0.0459 (11)	0.0597 (13)	0.0105 (9)	0.0113 (10)	0.0060 (10)
C3	0.0437 (11)	0.0577 (13)	0.0573 (13)	0.0083 (9)	−0.0054 (9)	0.0013 (10)
C4	0.0461 (10)	0.0427 (11)	0.0499 (11)	0.0013 (8)	−0.0072 (8)	−0.0017 (9)
C5	0.0391 (9)	0.0377 (9)	0.0348 (9)	0.0004 (7)	0.0019 (7)	0.0050 (7)
C6	0.0448 (11)	0.0429 (11)	0.0669 (14)	−0.0011 (9)	−0.0084 (9)	−0.0048 (10)
C7	0.0619 (14)	0.0384 (11)	0.0804 (16)	0.0004 (10)	0.0013 (12)	−0.0094 (10)
C8	0.0325 (9)	0.0502 (11)	0.0366 (9)	−0.0013 (8)	−0.0010 (7)	−0.0024 (8)
C9	0.0458 (11)	0.0631 (13)	0.0421 (11)	−0.0107 (9)	0.0082 (8)	−0.0081 (9)
C10	0.0530 (12)	0.0657 (14)	0.0558 (13)	−0.0064 (10)	0.0087 (10)	−0.0222 (11)
C11	0.0475 (11)	0.0507 (12)	0.0632 (14)	−0.0044 (9)	−0.0033 (10)	−0.0054 (10)
C12	0.0657 (14)	0.0617 (14)	0.0556 (13)	−0.0186 (11)	0.0106 (11)	0.0026 (11)
C13	0.0562 (12)	0.0604 (13)	0.0432 (11)	−0.0132 (10)	0.0111 (9)	−0.0082 (9)
C14	0.0800 (17)	0.0545 (14)	0.103 (2)	−0.0098 (13)	−0.0022 (15)	−0.0091 (14)
C15	0.0326 (9)	0.0460 (10)	0.0373 (9)	0.0011 (7)	−0.0022 (7)	0.0009 (8)
C16	0.0405 (10)	0.0446 (10)	0.0442 (11)	0.0056 (8)	−0.0030 (8)	−0.0038 (8)
C17	0.0431 (10)	0.0423 (10)	0.0427 (10)	−0.0013 (8)	0.0033 (8)	−0.0077 (8)
C18	0.0504 (11)	0.0487 (11)	0.0355 (10)	0.0053 (9)	0.0011 (8)	0.0014 (8)
C19	0.0391 (9)	0.0370 (9)	0.0339 (9)	0.0012 (7)	−0.0044 (7)	0.0012 (7)
C20	0.0449 (12)	0.0752 (15)	0.0650 (14)	0.0169 (11)	−0.0015 (10)	−0.0091 (12)
C21	0.0664 (14)	0.0447 (11)	0.0574 (13)	0.0061 (10)	−0.0057 (11)	−0.0001 (10)
C22	0.0396 (10)	0.0468 (10)	0.0392 (10)	−0.0015 (8)	−0.0002 (8)	0.0064 (8)
C23	0.0396 (10)	0.0571 (12)	0.0516 (12)	−0.0056 (9)	0.0025 (8)	0.0161 (10)
N1	0.0324 (7)	0.0433 (8)	0.0331 (8)	−0.0007 (6)	−0.0022 (6)	0.0033 (6)
O1	0.0448 (8)	0.1056 (13)	0.0410 (8)	−0.0026 (8)	−0.0019 (6)	0.0212 (8)
O2	0.0571 (9)	0.0680 (10)	0.0495 (8)	0.0061 (7)	0.0138 (7)	−0.0085 (7)
Cl1	0.0489 (3)	0.0632 (3)	0.0617 (3)	−0.0087 (2)	0.0092 (2)	0.0175 (3)

C1—C2	1.508 (3)	C14—H14B	0.9600
C1—H1A	0.9600	C14—H14C	0.9600
C1—H1B	0.9600	C15—N1	1.487 (2)
C1—H1C	0.9600	C15—C16	1.540 (3)
C2—C3	1.373 (3)	C15—H15	0.9800
C2—C7	1.377 (3)	C16—C17	1.516 (3)
C3—C4	1.380 (3)	C16—C20	1.531 (3)
C3—H3	0.9300	C16—C21	1.543 (3)
C4—C5	1.381 (3)	C17—O2	1.207 (2)
C4—H4	0.9300	C17—C18	1.509 (3)
C5—C6	1.381 (3)	C18—C19	1.531 (3)
C5—C19	1.518 (2)	C18—H18A	0.9700
C6—C7	1.379 (3)	C18—H18B	0.9700
C6—H6	0.9300	C19—N1	1.489 (2)
C7—H7	0.9300	C19—H19	0.9800
C8—C9	1.385 (3)	C20—H20A	0.9600
C8—C13	1.386 (3)	C20—H20B	0.9600
C8—C15	1.520 (3)	C20—H20C	0.9600
C9—C10	1.381 (3)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.376 (3)	C21—H21C	0.9600
C10—H10	0.9300	C22—O1	1.218 (2)
C11—C12	1.377 (3)	C22—N1	1.349 (2)
C11—C14	1.505 (3)	C22—C23	1.519 (3)
C12—C13	1.381 (3)	C23—Cl1	1.7644 (19)
C12—H12	0.9300	C23—H23A	0.9700
C13—H13	0.9300	C23—H23B	0.9700
C14—H14A	0.9600
C2—C1—H1A	109.5	C8—C15—C16	118.50 (15)
C2—C1—H1B	109.5	N1—C15—H15	106.0
H1A—C1—H1B	109.5	C8—C15—H15	106.0
C2—C1—H1C	109.5	C16—C15—H15	106.0
H1A—C1—H1C	109.5	C17—C16—C20	112.73 (17)
H1B—C1—H1C	109.5	C17—C16—C15	110.46 (15)
C3—C2—C7	117.28 (18)	C20—C16—C15	110.77 (16)
C3—C2—C1	121.0 (2)	C17—C16—C21	105.40 (15)
C7—C2—C1	121.7 (2)	C20—C16—C21	108.11 (17)
C2—C3—C4	121.64 (19)	C15—C16—C21	109.16 (16)
C2—C3—H3	119.2	O2—C17—C18	120.85 (18)
C4—C3—H3	119.2	O2—C17—C16	122.55 (18)
C3—C4—C5	121.03 (18)	C18—C17—C16	116.60 (16)
C3—C4—H4	119.5	C17—C18—C19	117.67 (16)
C5—C4—H4	119.5	C17—C18—H18A	107.9
C4—C5—C6	117.42 (17)	C19—C18—H18A	107.9
C4—C5—C19	120.27 (16)	C17—C18—H18B	107.9
C6—C5—C19	122.27 (16)	C19—C18—H18B	107.9
C7—C6—C5	121.02 (19)	H18A—C18—H18B	107.2
C7—C6—H6	119.5	N1—C19—C5	112.60 (14)
C5—C6—H6	119.5	N1—C19—C18	111.41 (14)
C2—C7—C6	121.6 (2)	C5—C19—C18	109.69 (14)
C2—C7—H7	119.2	N1—C19—H19	107.6
C6—C7—H7	119.2	C5—C19—H19	107.6
C9—C8—C13	116.72 (18)	C18—C19—H19	107.6
C9—C8—C15	117.68 (17)	C16—C20—H20A	109.5
C13—C8—C15	125.58 (17)	C16—C20—H20B	109.5
C10—C9—C8	121.54 (19)	H20A—C20—H20B	109.5
C10—C9—H9	119.2	C16—C20—H20C	109.5
C8—C9—H9	119.2	H20A—C20—H20C	109.5
C11—C10—C9	121.5 (2)	H20B—C20—H20C	109.5
C11—C10—H10	119.2	C16—C21—H21A	109.5
C9—C10—H10	119.2	C16—C21—H21B	109.5
C10—C11—C12	117.13 (19)	H21A—C21—H21B	109.5
C10—C11—C14	121.9 (2)	C16—C21—H21C	109.5
C12—C11—C14	121.0 (2)	H21A—C21—H21C	109.5
C11—C12—C13	121.8 (2)	H21B—C21—H21C	109.5
C11—C12—H12	119.1	O1—C22—N1	123.42 (17)
C13—C12—H12	119.1	O1—C22—C23	120.02 (17)
C12—C13—C8	121.27 (19)	N1—C22—C23	116.54 (15)
C12—C13—H13	119.4	C22—C23—Cl1	111.25 (13)
C8—C13—H13	119.4	C22—C23—H23A	109.4
C11—C14—H14A	109.5	Cl1—C23—H23A	109.4
C11—C14—H14B	109.5	C22—C23—H23B	109.4
H14A—C14—H14B	109.5	Cl1—C23—H23B	109.4
C11—C14—H14C	109.5	H23A—C23—H23B	108.0
H14A—C14—H14C	109.5	C22—N1—C15	117.32 (14)
H14B—C14—H14C	109.5	C22—N1—C19	122.34 (14)
N1—C15—C8	110.26 (14)	C15—N1—C19	119.73 (14)
N1—C15—C16	109.30 (14)
C7—C2—C3—C4	0.8 (3)	C8—C15—C16—C21	−176.06 (15)
C1—C2—C3—C4	−178.4 (2)	C20—C16—C17—O2	−31.5 (3)
C2—C3—C4—C5	−0.5 (3)	C15—C16—C17—O2	−156.03 (18)
C3—C4—C5—C6	−0.2 (3)	C21—C16—C17—O2	86.2 (2)
C3—C4—C5—C19	177.66 (18)	C20—C16—C17—C18	147.89 (18)
C4—C5—C6—C7	0.6 (3)	C15—C16—C17—C18	23.4 (2)
C19—C5—C6—C7	−177.3 (2)	C21—C16—C17—C18	−94.40 (19)
C3—C2—C7—C6	−0.4 (3)	O2—C17—C18—C19	−154.92 (18)
C1—C2—C7—C6	178.8 (2)	C16—C17—C18—C19	25.7 (2)
C5—C6—C7—C2	−0.2 (4)	C4—C5—C19—N1	129.92 (18)
C13—C8—C9—C10	−2.4 (3)	C6—C5—C19—N1	−52.3 (2)
C15—C8—C9—C10	175.93 (18)	C4—C5—C19—C18	−105.40 (19)
C8—C9—C10—C11	1.0 (3)	C6—C5—C19—C18	72.4 (2)
C9—C10—C11—C12	1.0 (3)	C17—C18—C19—N1	−37.9 (2)
C9—C10—C11—C14	−179.3 (2)	C17—C18—C19—C5	−163.28 (15)
C10—C11—C12—C13	−1.6 (3)	O1—C22—C23—Cl1	19.9 (3)
C14—C11—C12—C13	178.7 (2)	N1—C22—C23—Cl1	−161.74 (15)
C11—C12—C13—C8	0.2 (4)	O1—C22—N1—C15	−7.0 (3)
C9—C8—C13—C12	1.8 (3)	C23—C22—N1—C15	174.71 (16)
C15—C8—C13—C12	−176.37 (19)	O1—C22—N1—C19	−177.95 (18)
C9—C8—C15—N1	−70.5 (2)	C23—C22—N1—C19	3.7 (3)
C13—C8—C15—N1	107.6 (2)	C8—C15—N1—C22	105.19 (18)
C9—C8—C15—C16	162.48 (17)	C16—C15—N1—C22	−122.88 (17)
C13—C8—C15—C16	−19.4 (3)	C8—C15—N1—C19	−83.58 (18)
N1—C15—C16—C17	−58.92 (19)	C16—C15—N1—C19	48.3 (2)
C8—C15—C16—C17	68.5 (2)	C5—C19—N1—C22	−65.7 (2)
N1—C15—C16—C20	175.44 (16)	C18—C19—N1—C22	170.53 (16)
C8—C15—C16—C20	−57.1 (2)	C5—C19—N1—C15	123.48 (16)
N1—C15—C16—C21	56.52 (19)	C18—C19—N1—C15	−0.2 (2)