organic compounds
t-3-Pentyl-r-2,c-6-diphenylpiperidin-4-one
aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net
In the title molecule, C22H27NO, the piperidine ring adopts a chair conformation, with all substituents equatorial. The dihedral angle between the two phenyl rings is 56.90 (5)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds. A C—H⋯π interaction involving the phenyl ring at the 6-position is also found in the crystal structure.
Related literature
For a related et al. (2007). For the biological activity ofpiperidines, see: Venketeshperumal et al. (2001).
see: ThiruvalluvarExperimental
Crystal data
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Refinement
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Data collection: CrysAlis Pro (Oxford Diffraction, 2009); cell CrysAlis Pro; data reduction: CrysAlis Pro; 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: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809046753/wn2365sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809046753/wn2365Isup2.hkl
A mixture of ammonium acetate (38.5 g, 0.5 mol), benzaldehyde (106.12 ml, 1 mol) and 2-octanone (64.10 ml, 0.5 mol) in distilled ethanol was heated to boiling. After cooling the viscous liquid obtained was dissolved in diethyl ether (200 ml) and shaken with 10 ml concentrated hydrochloric acid. The precipitated hydrochloride of the title compound was removed by filtration and washed with 40 ml mixture of ethanol and diethyl ether (1:1) and then with diethyl ether to remove most of the coloured impurities. The base was liberated from an alcoholic solution by adding aqueous ammonia and then diluting with water. It was purified by
using an n-hexane-ethyl acetate mixture as the solvent. The yield of the compound was 80%.The N-bound H atom was located in a difference Fourier map and refined freely; N1—H1 = 0.911 (12) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 - 1.00 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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: PLATON (Spek, 2009).C22H27NO | F(000) = 696 |
Mr = 321.45 | Dx = 1.160 Mg m−3 |
Monoclinic, P21/n | Melting point: 368 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2318 (5) Å | Cell parameters from 5712 reflections |
b = 5.5879 (2) Å | θ = 4.9–32.7° |
c = 26.9977 (10) Å | µ = 0.07 mm−1 |
β = 94.377 (3)° | T = 110 K |
V = 1839.91 (12) Å3 | Rectangular-plate, colourless |
Z = 4 | 0.48 × 0.32 × 0.12 mm |
Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 6192 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4118 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.8°, θmin = 5.0° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −8→8 |
Tmin = 0.937, Tmax = 1.000 | l = −35→40 |
16194 measured reflections |
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) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3 |
6192 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C22H27NO | V = 1839.91 (12) Å3 |
Mr = 321.45 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.2318 (5) Å | µ = 0.07 mm−1 |
b = 5.5879 (2) Å | T = 110 K |
c = 26.9977 (10) Å | 0.48 × 0.32 × 0.12 mm |
β = 94.377 (3)° |
Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 6192 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 4118 reflections with I > 2σ(I) |
Tmin = 0.937, Tmax = 1.000 | Rint = 0.030 |
16194 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.31 e Å−3 |
6192 reflections | Δρmin = −0.18 e Å−3 |
221 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 > 2σ(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 | ||
O4 | −0.02984 (5) | 0.25856 (13) | 0.02836 (2) | 0.0227 (2) | |
N1 | 0.29439 (6) | 0.34289 (15) | 0.05803 (3) | 0.0171 (2) | |
C2 | 0.22093 (7) | 0.38195 (17) | 0.09795 (3) | 0.0165 (2) | |
C3 | 0.12069 (7) | 0.21283 (18) | 0.09013 (3) | 0.0169 (3) | |
C4 | 0.06862 (8) | 0.23999 (17) | 0.03724 (3) | 0.0173 (2) | |
C5 | 0.14663 (8) | 0.24418 (18) | −0.00331 (3) | 0.0192 (3) | |
C6 | 0.24286 (7) | 0.41460 (18) | 0.00937 (3) | 0.0172 (3) | |
C21 | 0.28492 (7) | 0.34132 (18) | 0.14743 (3) | 0.0172 (3) | |
C22 | 0.34717 (8) | 0.13503 (19) | 0.15574 (3) | 0.0207 (3) | |
C23 | 0.40971 (8) | 0.1003 (2) | 0.20020 (4) | 0.0255 (3) | |
C24 | 0.40946 (9) | 0.2723 (2) | 0.23750 (4) | 0.0291 (3) | |
C25 | 0.34617 (9) | 0.4751 (2) | 0.23009 (4) | 0.0293 (3) | |
C26 | 0.28428 (8) | 0.51060 (19) | 0.18526 (4) | 0.0225 (3) | |
C31 | 0.03717 (8) | 0.24628 (18) | 0.12901 (4) | 0.0201 (3) | |
C32 | −0.03780 (8) | 0.0314 (2) | 0.13360 (4) | 0.0221 (3) | |
C33 | −0.12480 (8) | 0.06791 (19) | 0.17050 (4) | 0.0219 (3) | |
C34 | −0.20306 (9) | −0.1429 (2) | 0.17217 (4) | 0.0299 (3) | |
C35 | −0.29164 (9) | −0.1088 (3) | 0.20818 (4) | 0.0348 (4) | |
C61 | 0.32404 (7) | 0.40532 (18) | −0.03020 (3) | 0.0173 (3) | |
C62 | 0.32447 (9) | 0.58540 (19) | −0.06565 (4) | 0.0248 (3) | |
C63 | 0.39528 (9) | 0.5724 (2) | −0.10367 (4) | 0.0294 (3) | |
C64 | 0.46508 (8) | 0.3801 (2) | −0.10661 (4) | 0.0264 (3) | |
C65 | 0.46548 (9) | 0.1999 (2) | −0.07135 (4) | 0.0276 (3) | |
C66 | 0.39528 (8) | 0.2136 (2) | −0.03327 (4) | 0.0241 (3) | |
H1 | 0.3572 (10) | 0.428 (2) | 0.0651 (4) | 0.021 (3)* | |
H2 | 0.19459 | 0.55139 | 0.09639 | 0.0197* | |
H3 | 0.14887 | 0.04518 | 0.09352 | 0.0203* | |
H5A | 0.10677 | 0.29558 | −0.03481 | 0.0230* | |
H5B | 0.17510 | 0.08071 | −0.00819 | 0.0230* | |
H6 | 0.21426 | 0.58156 | 0.01167 | 0.0206* | |
H22 | 0.34686 | 0.01608 | 0.13059 | 0.0249* | |
H23 | 0.45262 | −0.04059 | 0.20520 | 0.0306* | |
H24 | 0.45269 | 0.24994 | 0.26790 | 0.0349* | |
H25 | 0.34479 | 0.59133 | 0.25572 | 0.0351* | |
H26 | 0.24127 | 0.65141 | 0.18044 | 0.0270* | |
H31A | 0.07699 | 0.27722 | 0.16169 | 0.0242* | |
H31B | −0.00827 | 0.38878 | 0.12012 | 0.0242* | |
H32A | 0.00745 | −0.10925 | 0.14406 | 0.0266* | |
H32B | −0.07477 | −0.00435 | 0.10053 | 0.0266* | |
H33A | −0.08807 | 0.09314 | 0.20405 | 0.0263* | |
H33B | −0.16739 | 0.21403 | 0.16129 | 0.0263* | |
H34A | −0.16033 | −0.28830 | 0.18179 | 0.0359* | |
H34B | −0.23859 | −0.16958 | 0.13844 | 0.0359* | |
H35A | −0.33880 | −0.25068 | 0.20750 | 0.0522* | |
H35B | −0.33584 | 0.03216 | 0.19838 | 0.0522* | |
H35C | −0.25732 | −0.08574 | 0.24184 | 0.0522* | |
H62 | 0.27630 | 0.71802 | −0.06399 | 0.0298* | |
H63 | 0.39541 | 0.69675 | −0.12767 | 0.0352* | |
H64 | 0.51277 | 0.37121 | −0.13272 | 0.0317* | |
H65 | 0.51358 | 0.06723 | −0.07319 | 0.0331* | |
H66 | 0.39612 | 0.09009 | −0.00905 | 0.0289* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0151 (3) | 0.0264 (4) | 0.0265 (4) | −0.0013 (3) | 0.0007 (3) | 0.0036 (3) |
N1 | 0.0131 (4) | 0.0236 (4) | 0.0147 (3) | −0.0032 (3) | 0.0021 (3) | −0.0007 (3) |
C2 | 0.0157 (4) | 0.0180 (4) | 0.0160 (4) | −0.0013 (4) | 0.0035 (3) | −0.0019 (3) |
C3 | 0.0142 (4) | 0.0196 (5) | 0.0173 (4) | −0.0018 (4) | 0.0031 (3) | −0.0017 (4) |
C4 | 0.0157 (4) | 0.0148 (4) | 0.0213 (4) | −0.0026 (4) | 0.0013 (3) | −0.0008 (3) |
C5 | 0.0168 (4) | 0.0238 (5) | 0.0170 (4) | −0.0019 (4) | 0.0012 (3) | −0.0021 (4) |
C6 | 0.0160 (4) | 0.0189 (5) | 0.0168 (4) | 0.0000 (4) | 0.0018 (3) | 0.0002 (3) |
C21 | 0.0135 (4) | 0.0226 (5) | 0.0160 (4) | −0.0051 (4) | 0.0038 (3) | −0.0017 (4) |
C22 | 0.0178 (4) | 0.0252 (5) | 0.0196 (4) | −0.0017 (4) | 0.0041 (3) | −0.0013 (4) |
C23 | 0.0180 (5) | 0.0330 (6) | 0.0255 (5) | 0.0004 (4) | 0.0010 (4) | 0.0041 (4) |
C24 | 0.0237 (5) | 0.0440 (7) | 0.0192 (5) | −0.0096 (5) | −0.0015 (4) | 0.0018 (5) |
C25 | 0.0319 (6) | 0.0363 (6) | 0.0198 (5) | −0.0100 (5) | 0.0025 (4) | −0.0072 (4) |
C26 | 0.0232 (5) | 0.0236 (5) | 0.0211 (5) | −0.0044 (4) | 0.0051 (4) | −0.0040 (4) |
C31 | 0.0170 (4) | 0.0247 (5) | 0.0193 (4) | −0.0027 (4) | 0.0053 (3) | −0.0037 (4) |
C32 | 0.0209 (5) | 0.0265 (5) | 0.0197 (5) | −0.0039 (4) | 0.0060 (4) | −0.0012 (4) |
C33 | 0.0182 (4) | 0.0283 (5) | 0.0198 (4) | −0.0014 (4) | 0.0050 (3) | 0.0008 (4) |
C34 | 0.0253 (5) | 0.0393 (7) | 0.0260 (5) | −0.0101 (5) | 0.0072 (4) | −0.0004 (5) |
C35 | 0.0249 (5) | 0.0461 (8) | 0.0347 (6) | −0.0062 (5) | 0.0101 (5) | 0.0083 (5) |
C61 | 0.0150 (4) | 0.0216 (5) | 0.0153 (4) | −0.0044 (4) | 0.0011 (3) | −0.0013 (3) |
C62 | 0.0281 (5) | 0.0227 (5) | 0.0240 (5) | −0.0010 (4) | 0.0044 (4) | 0.0030 (4) |
C63 | 0.0345 (6) | 0.0324 (6) | 0.0219 (5) | −0.0099 (5) | 0.0071 (4) | 0.0057 (4) |
C64 | 0.0204 (5) | 0.0401 (7) | 0.0193 (5) | −0.0113 (5) | 0.0056 (4) | −0.0045 (4) |
C65 | 0.0208 (5) | 0.0364 (6) | 0.0263 (5) | 0.0020 (5) | 0.0066 (4) | −0.0025 (5) |
C66 | 0.0238 (5) | 0.0275 (5) | 0.0216 (5) | 0.0024 (4) | 0.0059 (4) | 0.0039 (4) |
O4—C4 | 1.2143 (12) | C2—H2 | 1.0000 |
N1—C2 | 1.4712 (11) | C3—H3 | 1.0000 |
N1—C6 | 1.4688 (12) | C5—H5A | 0.9900 |
N1—H1 | 0.911 (12) | C5—H5B | 0.9900 |
C2—C3 | 1.5497 (13) | C6—H6 | 1.0000 |
C2—C21 | 1.5130 (12) | C22—H22 | 0.9500 |
C3—C31 | 1.5310 (13) | C23—H23 | 0.9500 |
C3—C4 | 1.5260 (12) | C24—H24 | 0.9500 |
C4—C5 | 1.5063 (13) | C25—H25 | 0.9500 |
C5—C6 | 1.5323 (13) | C26—H26 | 0.9500 |
C6—C61 | 1.5139 (12) | C31—H31A | 0.9900 |
C21—C22 | 1.3903 (14) | C31—H31B | 0.9900 |
C21—C26 | 1.3925 (14) | C32—H32A | 0.9900 |
C22—C23 | 1.3869 (14) | C32—H32B | 0.9900 |
C23—C24 | 1.3922 (16) | C33—H33A | 0.9900 |
C24—C25 | 1.3784 (16) | C33—H33B | 0.9900 |
C25—C26 | 1.3919 (15) | C34—H34A | 0.9900 |
C31—C32 | 1.5216 (15) | C34—H34B | 0.9900 |
C32—C33 | 1.5259 (15) | C35—H35A | 0.9800 |
C33—C34 | 1.5207 (15) | C35—H35B | 0.9800 |
C34—C35 | 1.5219 (16) | C35—H35C | 0.9800 |
C61—C66 | 1.3874 (14) | C62—H62 | 0.9500 |
C61—C62 | 1.3890 (14) | C63—H63 | 0.9500 |
C62—C63 | 1.3946 (15) | C64—H64 | 0.9500 |
C63—C64 | 1.3785 (15) | C65—H65 | 0.9500 |
C64—C65 | 1.3854 (16) | C66—H66 | 0.9500 |
C65—C66 | 1.3910 (15) | ||
O4···C32 | 3.1202 (12) | H5A···O4i | 2.6700 |
O4···C6i | 3.2798 (11) | H5A···H32Bii | 2.4200 |
O4···C4i | 3.3294 (11) | H5B···C66 | 2.9200 |
O4···O4i | 3.2139 (10) | H5B···O4ii | 2.6300 |
O4···C4ii | 3.3158 (11) | H6···H2 | 2.3200 |
O4···C5ii | 3.2004 (12) | H6···H62 | 2.3600 |
O4···C5i | 3.1736 (12) | H6···O4i | 2.5900 |
O4···H32B | 2.5300 | H22···N1 | 2.7200 |
O4···H31B | 2.5800 | H22···C3 | 3.1000 |
O4···H5Ai | 2.6700 | H22···H3 | 2.5500 |
O4···H5Bii | 2.6300 | H22···H65ix | 2.4400 |
O4···H6i | 2.5900 | H23···C25vi | 3.1000 |
N1···H22 | 2.7200 | H24···H32Aiv | 2.5200 |
N1···H66 | 2.6800 | H25···H31Aiv | 2.5800 |
C4···O4i | 3.3294 (11) | H26···C22vii | 3.0900 |
C4···O4ii | 3.3158 (11) | H26···H2 | 2.3600 |
C5···O4ii | 3.2004 (12) | H26···C24iv | 3.0600 |
C5···O4i | 3.1736 (12) | H31A···C21 | 2.6300 |
C6···O4i | 3.2798 (11) | H31A···C26 | 2.8800 |
C24···C26iii | 3.5857 (15) | H31A···H25iii | 2.5800 |
C26···C31 | 3.5949 (14) | H31B···O4 | 2.5800 |
C26···C24iv | 3.5857 (15) | H31B···H33B | 2.5100 |
C31···C26 | 3.5949 (14) | H32A···H3 | 2.4400 |
C32···O4 | 3.1202 (12) | H32A···H34A | 2.5600 |
C3···H22 | 3.1000 | H32A···H24iii | 2.5200 |
C4···H32B | 2.8800 | H32B···O4 | 2.5300 |
C5···H32Bii | 3.0200 | H32B···C4 | 2.8800 |
C21···H64v | 3.0000 | H32B···H34B | 2.5000 |
C21···H31A | 2.6300 | H32B···C5ii | 3.0200 |
C22···H26vi | 3.0900 | H32B···H5Aii | 2.4200 |
C22···H3 | 2.8900 | H33A···H35C | 2.5800 |
C22···H1 | 2.955 (11) | H33B···H31B | 2.5100 |
C24···H26iii | 3.0600 | H33B···H35B | 2.5700 |
C25···H23vii | 3.1000 | H34A···H32A | 2.5600 |
C26···H64v | 3.0200 | H34B···H32B | 2.5000 |
C26···H31A | 2.8800 | H34B···C63ii | 3.0600 |
C35···H35Cviii | 3.0300 | H34B···C64ii | 3.0700 |
C63···H34Bii | 3.0600 | H35A···H35Cviii | 2.5500 |
C64···H1v | 2.600 (12) | H35B···H33B | 2.5700 |
C64···H34Bii | 3.0700 | H35B···H63i | 2.5000 |
C65···H1v | 3.000 (12) | H35C···H33A | 2.5800 |
C66···H1 | 2.982 (11) | H35C···C35x | 3.0300 |
C66···H5B | 2.9200 | H35C···H35Ax | 2.5500 |
H1···C22 | 2.955 (11) | H62···H6 | 2.3600 |
H1···C66 | 2.982 (11) | H63···H35Bi | 2.5000 |
H1···C64v | 2.600 (12) | H64···C21v | 3.0000 |
H1···C65v | 3.000 (12) | H64···C26v | 3.0200 |
H1···H64v | 2.5800 | H64···H1v | 2.5800 |
H2···H6 | 2.3200 | H65···H22ix | 2.4400 |
H2···H26 | 2.3600 | H65···H66ix | 2.5600 |
H3···C22 | 2.8900 | H66···N1 | 2.6800 |
H3···H22 | 2.5500 | H66···H65ix | 2.5600 |
H3···H32A | 2.4400 | ||
C2—N1—C6 | 111.74 (7) | C5—C6—H6 | 109.00 |
C6—N1—H1 | 110.0 (7) | C61—C6—H6 | 109.00 |
C2—N1—H1 | 108.8 (7) | C21—C22—H22 | 120.00 |
N1—C2—C21 | 108.71 (7) | C23—C22—H22 | 120.00 |
N1—C2—C3 | 109.32 (7) | C22—C23—H23 | 120.00 |
C3—C2—C21 | 112.30 (7) | C24—C23—H23 | 120.00 |
C4—C3—C31 | 112.13 (8) | C23—C24—H24 | 120.00 |
C2—C3—C4 | 109.65 (7) | C25—C24—H24 | 120.00 |
C2—C3—C31 | 113.24 (7) | C24—C25—H25 | 120.00 |
O4—C4—C5 | 121.93 (7) | C26—C25—H25 | 120.00 |
O4—C4—C3 | 122.01 (8) | C21—C26—H26 | 120.00 |
C3—C4—C5 | 116.06 (8) | C25—C26—H26 | 120.00 |
C4—C5—C6 | 111.45 (7) | C3—C31—H31A | 109.00 |
N1—C6—C5 | 107.47 (7) | C3—C31—H31B | 109.00 |
C5—C6—C61 | 110.80 (7) | C32—C31—H31A | 109.00 |
N1—C6—C61 | 111.22 (7) | C32—C31—H31B | 109.00 |
C2—C21—C26 | 120.94 (9) | H31A—C31—H31B | 108.00 |
C2—C21—C22 | 120.46 (8) | C31—C32—H32A | 109.00 |
C22—C21—C26 | 118.59 (8) | C31—C32—H32B | 109.00 |
C21—C22—C23 | 120.99 (9) | C33—C32—H32A | 109.00 |
C22—C23—C24 | 119.86 (10) | C33—C32—H32B | 109.00 |
C23—C24—C25 | 119.66 (10) | H32A—C32—H32B | 108.00 |
C24—C25—C26 | 120.37 (10) | C32—C33—H33A | 109.00 |
C21—C26—C25 | 120.52 (9) | C32—C33—H33B | 109.00 |
C3—C31—C32 | 113.41 (8) | C34—C33—H33A | 109.00 |
C31—C32—C33 | 113.72 (9) | C34—C33—H33B | 109.00 |
C32—C33—C34 | 112.81 (9) | H33A—C33—H33B | 108.00 |
C33—C34—C35 | 113.73 (10) | C33—C34—H34A | 109.00 |
C6—C61—C62 | 119.91 (9) | C33—C34—H34B | 109.00 |
C62—C61—C66 | 118.87 (9) | C35—C34—H34A | 109.00 |
C6—C61—C66 | 121.16 (9) | C35—C34—H34B | 109.00 |
C61—C62—C63 | 120.31 (10) | H34A—C34—H34B | 108.00 |
C62—C63—C64 | 120.34 (10) | C34—C35—H35A | 109.00 |
C63—C64—C65 | 119.78 (10) | C34—C35—H35B | 109.00 |
C64—C65—C66 | 119.86 (10) | C34—C35—H35C | 109.00 |
C61—C66—C65 | 120.84 (10) | H35A—C35—H35B | 109.00 |
N1—C2—H2 | 109.00 | H35A—C35—H35C | 109.00 |
C3—C2—H2 | 109.00 | H35B—C35—H35C | 109.00 |
C21—C2—H2 | 109.00 | C61—C62—H62 | 120.00 |
C2—C3—H3 | 107.00 | C63—C62—H62 | 120.00 |
C4—C3—H3 | 107.00 | C62—C63—H63 | 120.00 |
C31—C3—H3 | 107.00 | C64—C63—H63 | 120.00 |
C4—C5—H5A | 109.00 | C63—C64—H64 | 120.00 |
C4—C5—H5B | 109.00 | C65—C64—H64 | 120.00 |
C6—C5—H5A | 109.00 | C64—C65—H65 | 120.00 |
C6—C5—H5B | 109.00 | C66—C65—H65 | 120.00 |
H5A—C5—H5B | 108.00 | C61—C66—H66 | 120.00 |
N1—C6—H6 | 109.00 | C65—C66—H66 | 120.00 |
C6—N1—C2—C3 | 65.82 (9) | N1—C6—C61—C66 | 44.07 (12) |
C6—N1—C2—C21 | −171.28 (8) | C5—C6—C61—C62 | 101.57 (10) |
C2—N1—C6—C5 | −66.24 (9) | C5—C6—C61—C66 | −75.40 (11) |
C2—N1—C6—C61 | 172.32 (8) | C2—C21—C22—C23 | 177.34 (9) |
N1—C2—C3—C4 | −51.99 (10) | C26—C21—C22—C23 | −1.64 (14) |
N1—C2—C3—C31 | −178.04 (8) | C2—C21—C26—C25 | −177.96 (9) |
C21—C2—C3—C4 | −172.73 (7) | C22—C21—C26—C25 | 1.02 (14) |
C21—C2—C3—C31 | 61.21 (10) | C21—C22—C23—C24 | 0.85 (15) |
N1—C2—C21—C22 | −49.98 (11) | C22—C23—C24—C25 | 0.58 (16) |
N1—C2—C21—C26 | 128.98 (9) | C23—C24—C25—C26 | −1.19 (16) |
C3—C2—C21—C22 | 71.12 (11) | C24—C25—C26—C21 | 0.38 (16) |
C3—C2—C21—C26 | −109.92 (10) | C3—C31—C32—C33 | −177.25 (8) |
C2—C3—C4—O4 | −134.43 (9) | C31—C32—C33—C34 | 176.50 (9) |
C2—C3—C4—C5 | 45.15 (11) | C32—C33—C34—C35 | −179.13 (9) |
C31—C3—C4—O4 | −7.74 (13) | C6—C61—C62—C63 | −176.86 (9) |
C31—C3—C4—C5 | 171.84 (8) | C66—C61—C62—C63 | 0.17 (15) |
C2—C3—C31—C32 | −159.31 (8) | C6—C61—C66—C65 | 176.46 (9) |
C4—C3—C31—C32 | 75.97 (11) | C62—C61—C66—C65 | −0.54 (15) |
O4—C4—C5—C6 | 132.23 (9) | C61—C62—C63—C64 | 0.37 (16) |
C3—C4—C5—C6 | −47.35 (11) | C62—C63—C64—C65 | −0.55 (16) |
C4—C5—C6—N1 | 54.81 (10) | C63—C64—C65—C66 | 0.18 (16) |
C4—C5—C6—C61 | 176.51 (8) | C64—C65—C66—C61 | 0.37 (16) |
N1—C6—C61—C62 | −138.96 (9) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+1, −y+1, −z; (vi) x, y−1, z; (vii) x, y+1, z; (viii) −x−1/2, y−1/2, −z+1/2; (ix) −x+1, −y, −z; (x) −x−1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O4i | 1.00 | 2.59 | 3.2798 (11) | 126 |
C34—H34B···Cg1ii | 0.99 | 2.87 | 3.7809 (12) | 154 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H27NO |
Mr | 321.45 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 110 |
a, b, c (Å) | 12.2318 (5), 5.5879 (2), 26.9977 (10) |
β (°) | 94.377 (3) |
V (Å3) | 1839.91 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.48 × 0.32 × 0.12 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Ruby Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.937, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16194, 6192, 4118 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.763 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.121, 0.96 |
No. of reflections | 6192 |
No. of parameters | 221 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.18 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O4i | 1.00 | 2.59 | 3.2798 (11) | 126 |
C34—H34B···Cg1ii | 0.99 | 2.87 | 3.7809 (12) | 154 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z. |
Acknowledgements
RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England. 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
Thiruvalluvar, A., Balamurugan, S., Jayabharathi, J., Manimekalai, A. & Rajarajan, G. (2007). Acta Cryst. E63, o2886. Web of Science CSD CrossRef IUCr Journals Google Scholar
Venketeshperumal, R., Adiraj, M. & Shanmugapandian, P. (2001). Indian Drugs, 38, 167–169. 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 exhibit a wide spectrum of biological activities and form an essential part of the molecular structures of important drugs. Molecular geometry critically influences biological activity. Attention has been focused on structure-activity relationships. Piperidines with crowded groups at C3 and C5 have enhanced biological activity compared to other piperidines (Venketeshperumal et al., 2001).
As part of our research, we have synthesized the title compound and report its crystal structure here. Thiruvalluvar et al., (2007) have reported the crystal structure of a diphenylpiperidin-4-ol derivative, in which the piperidine ring adopts a chair conformation.
In the title molecule, C22H27NO, (Fig.1) the piperidine ring adopts a chair conformation, with all substituents equatorial. The dihedral angle between the two phenyl rings is 56.90 (5)°. Molecules are linked by C6—H6···O4(-x, 1 - y, -z) weak hydrogen bonds. A C34—H34B···π (-x, -y, -z) interaction involving the phenyl ring (C61—C66) is also found in the crystal structure.