![cross.png](/logos/buttonlogos/cross.png)
![cross.png](/logos/buttonlogos/cross.png)
organic compounds
p-tolylpiperidin-4-one
of 1-(2-chloroacetyl)-3,3-dimethyl-2,6-di-aDrug Discovery Lab., Department of Chemistry, Annamalai University, Annamalai Nagar, Tamil Nadu 608 002, India, and bDivision of Life Sciences, Central Instrumentation Facility, Institute of Advanced Study in Science & Technology (IASST), Guwahati 781 035, Assam, India
*Correspondence e-mail: kabilanchem60@rediffmail.com
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 intermolecular interactions present.
Keywords: crystal structure; piperidones; piperidin-4-one; p-tolyl.
CCDC reference: 1030980
1. 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
).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2004); cell 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
).
Supporting information
CCDC reference: 1030980
10.1107/S2056989015002613/su5059sup1.cif
contains datablocks I, publication_text. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015002613/su5059Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015002613/su5059Isup3.cml
The title compound was synthesized according to a published procedure (Aridoss et al., 2007). To a well stirred solution of 3, 3-dimethyl-2, 6-di-p-tolyl piperidin-4-one (5 mmol), and triethylamine (5 mmol) in 20 ml of benzene, dichloroacetylchloride (5 mmol) in 20 ml of benzene was added drop wise through the additional funnel over ca. 30 min. Stirring was continued with mild heating using a magnetic stirrer for 7 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was poured into water and extracted with ether. The collected ether extracts were then washed well with 3% sodium bicarbonate solution and dried over anhydrous Na2SO4. The pasty mass obtained was purified by crystallization from distilled ethanol giving the compound in pure form as colourless block-like crystals.
H atoms were positioned geometrically and refined using a riding model: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
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 (Sheldrick, 2008) and PLATON (Spek, 2009). ![]() | Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. |
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 |
C23H26ClNO2 | V = 4122.6 (2) Å3 |
Mr = 383.90 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.7923 (6) Å | µ = 0.20 mm−1 |
b = 18.8289 (5) Å | T = 296 K |
c = 11.6689 (3) Å | 0.35 × 0.30 × 0.25 mm |
β = 93.162 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3989 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3097 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.959 | Rint = 0.028 |
29055 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.30 e Å−3 |
3989 reflections | Δρmin = −0.22 e Å−3 |
244 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C23H26ClNO2 |
Mr | 383.90 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 18.7923 (6), 18.8289 (5), 11.6689 (3) |
β (°) | 93.162 (2) |
V (Å3) | 4122.6 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.931, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29055, 3989, 3097 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.613 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.124, 1.03 |
No. of reflections | 3989 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.22 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
SJ is thankful to the CSIR, New Delhi, for the award of a Senior Research Fellowship through research grant No. 01/2454/11/EMR-II, and is also grateful to the UGC for the award of a UGC–BSR fellowship through a Research Fellowship in Science for Meritorious Students (RFSMS). The authors acknowledge the SAIF, IIT Madras, for the data collection.
References
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Aridoss, G., Balasubramanian, S., Parthiban, P. & Kabilan, S. (2007). Spectrochim. Acta Part A, 68, 1153–1163. Web of Science CrossRef CAS Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balzarini, J., De Clercq, E. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586–593. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Krishnakumar, R. & Krishnapillay, M. (1996). Indian J. Chem. Sect. B, 35, 418–425. Google Scholar
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 2981–2985. Web of Science CSD CrossRef PubMed CAS Google Scholar
Perumal, R. V., Agiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156–159. Google Scholar
Ravindran, T., Jeyaraman, R., Murray, R. W. & Singh, M. J. (1991). J. Org. Chem. 56, 4833–4840. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Piperidones are an important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities, including cytotoxic properties (Dimmock et al., 2001). They were also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001). The present investigation was undertaken to establish the structure, conformation of the heterocyclic ring and orientation of the 4-tolyl groups in the title compound.
The molecular structure of the title compound is illustrated in Fig. 1. The sum of the bond angles around atom N1 is 359.39° indicating sp2 hybridization. The N1—C22 [1.349 (2) Å] and C22—O1[1.218 (2) Å] bond distances indicate electron delocalization. The six membered piperidine ring (N1/C15-C19) adopts a distorted boat conformation. The two p-tolyl rings are nearly orthogonal to each other with a dihedral angle of 83.33 (10)°. The methyl substituents are oriented equatorially [N1—C15—C16—C20 = 175 (16)°] and axially [N1—C15—C16—C21 = 56.52 (19)°] at the C3 position. The two p-tolyl (C2-C7 and C8-C13) are inclined to the mean plane of the piperidine ring by 73.2 (1) and 87.22 (9) °, respectively.
In the crystal, there are no significant intermolecular interactions present.