Literature DB >> 21578813

t-3-Pentyl-r-2,c-6-diphenyl-piperidin-4-one.

P Gayathri, J Jayabharathi, G Rajarajan, A Thiruvalluvar, R J Butcher.   

Abstract

In the title mol-ecule, C(22)H(27)NO, 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, mol-ecules are linked by weak C-H⋯O n class="Chemical">hydrogen bonds. A C-H⋯π inter-action involving the phenyl ring at the 6-position is also found in the crystal structure.

Entities:  

Year:  2009        PMID： 21578813      PMCID： PMC2971784          DOI： 10.1107/S1600536809046753

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a related crystal structure, see: Thiruvalluvar et al. (2007 ▶). For the biological activity ofpiperidines, see: Venketeshperumal et al. (2001 ▶).

Experimental

Crystal data

C22H27NO M = 321.45 Monoclinic, a = 12.2318 (5) Å b = 5.5879 (2) Å c = 26.9977 (10) Å β = 94.377 (3)° V = 1839.91 (12) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 110 K 0.48 × 0.32 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.937, T max = 1.000 16194 measured reflections 6192 independent reflections 4118 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.121 S = 0.96 6192 reflections 221 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.31 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046753/wn2365sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046753/wn2365Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H27NOF(000) = 696
Mr = 321.45Dx = 1.160 Mg m−3
Monoclinic, P21/nMelting point: 368 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.2318 (5) ÅCell parameters from 5712 reflections
b = 5.5879 (2) Åθ = 4.9–32.7°
c = 26.9977 (10) ŵ = 0.07 mm−1
β = 94.377 (3)°T = 110 K
V = 1839.91 (12) Å3Rectangular-plate, colourless
Z = 40.48 × 0.32 × 0.12 mm
Oxford Diffraction Xcalibur Ruby Gemini diffractometer6192 independent reflections
Radiation source: Enhance (Mo) X-ray Source4118 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.5081 pixels mm-1θmax = 32.8°, θmin = 5.0°
ω scansh = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −8→8
Tmin = 0.937, Tmax = 1.000l = −35→40
16194 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 0.96w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3
6192 reflections(Δ/σ)max = 0.001
221 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
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.
xyzUiso*/Ueq
O4−0.02984 (5)0.25856 (13)0.02836 (2)0.0227 (2)
N10.29439 (6)0.34289 (15)0.05803 (3)0.0171 (2)
C20.22093 (7)0.38195 (17)0.09795 (3)0.0165 (2)
C30.12069 (7)0.21283 (18)0.09013 (3)0.0169 (3)
C40.06862 (8)0.23999 (17)0.03724 (3)0.0173 (2)
C50.14663 (8)0.24418 (18)−0.00331 (3)0.0192 (3)
C60.24286 (7)0.41460 (18)0.00937 (3)0.0172 (3)
C210.28492 (7)0.34132 (18)0.14743 (3)0.0172 (3)
C220.34717 (8)0.13503 (19)0.15574 (3)0.0207 (3)
C230.40971 (8)0.1003 (2)0.20020 (4)0.0255 (3)
C240.40946 (9)0.2723 (2)0.23750 (4)0.0291 (3)
C250.34617 (9)0.4751 (2)0.23009 (4)0.0293 (3)
C260.28428 (8)0.51060 (19)0.18526 (4)0.0225 (3)
C310.03717 (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)
C610.32404 (7)0.40532 (18)−0.03020 (3)0.0173 (3)
C620.32447 (9)0.58540 (19)−0.06565 (4)0.0248 (3)
C630.39528 (9)0.5724 (2)−0.10367 (4)0.0294 (3)
C640.46508 (8)0.3801 (2)−0.10661 (4)0.0264 (3)
C650.46548 (9)0.1999 (2)−0.07135 (4)0.0276 (3)
C660.39528 (8)0.2136 (2)−0.03327 (4)0.0241 (3)
H10.3572 (10)0.428 (2)0.0651 (4)0.021 (3)*
H20.194590.551390.096390.0197*
H30.148870.045180.093520.0203*
H5A0.106770.29558−0.034810.0230*
H5B0.175100.08071−0.008190.0230*
H60.214260.581560.011670.0206*
H220.346860.016080.130590.0249*
H230.45262−0.040590.205200.0306*
H240.452690.249940.267900.0349*
H250.344790.591330.255720.0351*
H260.241270.651410.180440.0270*
H31A0.076990.277220.161690.0242*
H31B−0.008270.388780.120120.0242*
H32A0.00745−0.109250.144060.0266*
H32B−0.07477−0.004350.100530.0266*
H33A−0.088070.093140.204050.0263*
H33B−0.167390.214030.161290.0263*
H34A−0.16033−0.288300.181790.0359*
H34B−0.23859−0.169580.138440.0359*
H35A−0.33880−0.250680.207500.0522*
H35B−0.335840.032160.198380.0522*
H35C−0.25732−0.085740.241840.0522*
H620.276300.71802−0.063990.0298*
H630.395410.69675−0.127670.0352*
H640.512770.37121−0.132720.0317*
H650.513580.06723−0.073190.0331*
H660.396120.09009−0.009050.0289*
U11U22U33U12U13U23
O40.0151 (3)0.0264 (4)0.0265 (4)−0.0013 (3)0.0007 (3)0.0036 (3)
N10.0131 (4)0.0236 (4)0.0147 (3)−0.0032 (3)0.0021 (3)−0.0007 (3)
C20.0157 (4)0.0180 (4)0.0160 (4)−0.0013 (4)0.0035 (3)−0.0019 (3)
C30.0142 (4)0.0196 (5)0.0173 (4)−0.0018 (4)0.0031 (3)−0.0017 (4)
C40.0157 (4)0.0148 (4)0.0213 (4)−0.0026 (4)0.0013 (3)−0.0008 (3)
C50.0168 (4)0.0238 (5)0.0170 (4)−0.0019 (4)0.0012 (3)−0.0021 (4)
C60.0160 (4)0.0189 (5)0.0168 (4)0.0000 (4)0.0018 (3)0.0002 (3)
C210.0135 (4)0.0226 (5)0.0160 (4)−0.0051 (4)0.0038 (3)−0.0017 (4)
C220.0178 (4)0.0252 (5)0.0196 (4)−0.0017 (4)0.0041 (3)−0.0013 (4)
C230.0180 (5)0.0330 (6)0.0255 (5)0.0004 (4)0.0010 (4)0.0041 (4)
C240.0237 (5)0.0440 (7)0.0192 (5)−0.0096 (5)−0.0015 (4)0.0018 (5)
C250.0319 (6)0.0363 (6)0.0198 (5)−0.0100 (5)0.0025 (4)−0.0072 (4)
C260.0232 (5)0.0236 (5)0.0211 (5)−0.0044 (4)0.0051 (4)−0.0040 (4)
C310.0170 (4)0.0247 (5)0.0193 (4)−0.0027 (4)0.0053 (3)−0.0037 (4)
C320.0209 (5)0.0265 (5)0.0197 (5)−0.0039 (4)0.0060 (4)−0.0012 (4)
C330.0182 (4)0.0283 (5)0.0198 (4)−0.0014 (4)0.0050 (3)0.0008 (4)
C340.0253 (5)0.0393 (7)0.0260 (5)−0.0101 (5)0.0072 (4)−0.0004 (5)
C350.0249 (5)0.0461 (8)0.0347 (6)−0.0062 (5)0.0101 (5)0.0083 (5)
C610.0150 (4)0.0216 (5)0.0153 (4)−0.0044 (4)0.0011 (3)−0.0013 (3)
C620.0281 (5)0.0227 (5)0.0240 (5)−0.0010 (4)0.0044 (4)0.0030 (4)
C630.0345 (6)0.0324 (6)0.0219 (5)−0.0099 (5)0.0071 (4)0.0057 (4)
C640.0204 (5)0.0401 (7)0.0193 (5)−0.0113 (5)0.0056 (4)−0.0045 (4)
C650.0208 (5)0.0364 (6)0.0263 (5)0.0020 (5)0.0066 (4)−0.0025 (5)
C660.0238 (5)0.0275 (5)0.0216 (5)0.0024 (4)0.0059 (4)0.0039 (4)
O4—C41.2143 (12)C2—H21.0000
N1—C21.4712 (11)C3—H31.0000
N1—C61.4688 (12)C5—H5A0.9900
N1—H10.911 (12)C5—H5B0.9900
C2—C31.5497 (13)C6—H61.0000
C2—C211.5130 (12)C22—H220.9500
C3—C311.5310 (13)C23—H230.9500
C3—C41.5260 (12)C24—H240.9500
C4—C51.5063 (13)C25—H250.9500
C5—C61.5323 (13)C26—H260.9500
C6—C611.5139 (12)C31—H31A0.9900
C21—C221.3903 (14)C31—H31B0.9900
C21—C261.3925 (14)C32—H32A0.9900
C22—C231.3869 (14)C32—H32B0.9900
C23—C241.3922 (16)C33—H33A0.9900
C24—C251.3784 (16)C33—H33B0.9900
C25—C261.3919 (15)C34—H34A0.9900
C31—C321.5216 (15)C34—H34B0.9900
C32—C331.5259 (15)C35—H35A0.9800
C33—C341.5207 (15)C35—H35B0.9800
C34—C351.5219 (16)C35—H35C0.9800
C61—C661.3874 (14)C62—H620.9500
C61—C621.3890 (14)C63—H630.9500
C62—C631.3946 (15)C64—H640.9500
C63—C641.3785 (15)C65—H650.9500
C64—C651.3854 (16)C66—H660.9500
C65—C661.3910 (15)
O4···C323.1202 (12)H5A···O4i2.6700
O4···C6i3.2798 (11)H5A···H32Bii2.4200
O4···C4i3.3294 (11)H5B···C662.9200
O4···O4i3.2139 (10)H5B···O4ii2.6300
O4···C4ii3.3158 (11)H6···H22.3200
O4···C5ii3.2004 (12)H6···H622.3600
O4···C5i3.1736 (12)H6···O4i2.5900
O4···H32B2.5300H22···N12.7200
O4···H31B2.5800H22···C33.1000
O4···H5Ai2.6700H22···H32.5500
O4···H5Bii2.6300H22···H65ix2.4400
O4···H6i2.5900H23···C25vi3.1000
N1···H222.7200H24···H32Aiv2.5200
N1···H662.6800H25···H31Aiv2.5800
C4···O4i3.3294 (11)H26···C22vii3.0900
C4···O4ii3.3158 (11)H26···H22.3600
C5···O4ii3.2004 (12)H26···C24iv3.0600
C5···O4i3.1736 (12)H31A···C212.6300
C6···O4i3.2798 (11)H31A···C262.8800
C24···C26iii3.5857 (15)H31A···H25iii2.5800
C26···C313.5949 (14)H31B···O42.5800
C26···C24iv3.5857 (15)H31B···H33B2.5100
C31···C263.5949 (14)H32A···H32.4400
C32···O43.1202 (12)H32A···H34A2.5600
C3···H223.1000H32A···H24iii2.5200
C4···H32B2.8800H32B···O42.5300
C5···H32Bii3.0200H32B···C42.8800
C21···H64v3.0000H32B···H34B2.5000
C21···H31A2.6300H32B···C5ii3.0200
C22···H26vi3.0900H32B···H5Aii2.4200
C22···H32.8900H33A···H35C2.5800
C22···H12.955 (11)H33B···H31B2.5100
C24···H26iii3.0600H33B···H35B2.5700
C25···H23vii3.1000H34A···H32A2.5600
C26···H64v3.0200H34B···H32B2.5000
C26···H31A2.8800H34B···C63ii3.0600
C35···H35Cviii3.0300H34B···C64ii3.0700
C63···H34Bii3.0600H35A···H35Cviii2.5500
C64···H1v2.600 (12)H35B···H33B2.5700
C64···H34Bii3.0700H35B···H63i2.5000
C65···H1v3.000 (12)H35C···H33A2.5800
C66···H12.982 (11)H35C···C35x3.0300
C66···H5B2.9200H35C···H35Ax2.5500
H1···C222.955 (11)H62···H62.3600
H1···C662.982 (11)H63···H35Bi2.5000
H1···C64v2.600 (12)H64···C21v3.0000
H1···C65v3.000 (12)H64···C26v3.0200
H1···H64v2.5800H64···H1v2.5800
H2···H62.3200H65···H22ix2.4400
H2···H262.3600H65···H66ix2.5600
H3···C222.8900H66···N12.6800
H3···H222.5500H66···H65ix2.5600
H3···H32A2.4400
C2—N1—C6111.74 (7)C5—C6—H6109.00
C6—N1—H1110.0 (7)C61—C6—H6109.00
C2—N1—H1108.8 (7)C21—C22—H22120.00
N1—C2—C21108.71 (7)C23—C22—H22120.00
N1—C2—C3109.32 (7)C22—C23—H23120.00
C3—C2—C21112.30 (7)C24—C23—H23120.00
C4—C3—C31112.13 (8)C23—C24—H24120.00
C2—C3—C4109.65 (7)C25—C24—H24120.00
C2—C3—C31113.24 (7)C24—C25—H25120.00
O4—C4—C5121.93 (7)C26—C25—H25120.00
O4—C4—C3122.01 (8)C21—C26—H26120.00
C3—C4—C5116.06 (8)C25—C26—H26120.00
C4—C5—C6111.45 (7)C3—C31—H31A109.00
N1—C6—C5107.47 (7)C3—C31—H31B109.00
C5—C6—C61110.80 (7)C32—C31—H31A109.00
N1—C6—C61111.22 (7)C32—C31—H31B109.00
C2—C21—C26120.94 (9)H31A—C31—H31B108.00
C2—C21—C22120.46 (8)C31—C32—H32A109.00
C22—C21—C26118.59 (8)C31—C32—H32B109.00
C21—C22—C23120.99 (9)C33—C32—H32A109.00
C22—C23—C24119.86 (10)C33—C32—H32B109.00
C23—C24—C25119.66 (10)H32A—C32—H32B108.00
C24—C25—C26120.37 (10)C32—C33—H33A109.00
C21—C26—C25120.52 (9)C32—C33—H33B109.00
C3—C31—C32113.41 (8)C34—C33—H33A109.00
C31—C32—C33113.72 (9)C34—C33—H33B109.00
C32—C33—C34112.81 (9)H33A—C33—H33B108.00
C33—C34—C35113.73 (10)C33—C34—H34A109.00
C6—C61—C62119.91 (9)C33—C34—H34B109.00
C62—C61—C66118.87 (9)C35—C34—H34A109.00
C6—C61—C66121.16 (9)C35—C34—H34B109.00
C61—C62—C63120.31 (10)H34A—C34—H34B108.00
C62—C63—C64120.34 (10)C34—C35—H35A109.00
C63—C64—C65119.78 (10)C34—C35—H35B109.00
C64—C65—C66119.86 (10)C34—C35—H35C109.00
C61—C66—C65120.84 (10)H35A—C35—H35B109.00
N1—C2—H2109.00H35A—C35—H35C109.00
C3—C2—H2109.00H35B—C35—H35C109.00
C21—C2—H2109.00C61—C62—H62120.00
C2—C3—H3107.00C63—C62—H62120.00
C4—C3—H3107.00C62—C63—H63120.00
C31—C3—H3107.00C64—C63—H63120.00
C4—C5—H5A109.00C63—C64—H64120.00
C4—C5—H5B109.00C65—C64—H64120.00
C6—C5—H5A109.00C64—C65—H65120.00
C6—C5—H5B109.00C66—C65—H65120.00
H5A—C5—H5B108.00C61—C66—H66120.00
N1—C6—H6109.00C65—C66—H66120.00
C6—N1—C2—C365.82 (9)N1—C6—C61—C6644.07 (12)
C6—N1—C2—C21−171.28 (8)C5—C6—C61—C62101.57 (10)
C2—N1—C6—C5−66.24 (9)C5—C6—C61—C66−75.40 (11)
C2—N1—C6—C61172.32 (8)C2—C21—C22—C23177.34 (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—C251.02 (14)
C21—C2—C3—C3161.21 (10)C21—C22—C23—C240.85 (15)
N1—C2—C21—C22−49.98 (11)C22—C23—C24—C250.58 (16)
N1—C2—C21—C26128.98 (9)C23—C24—C25—C26−1.19 (16)
C3—C2—C21—C2271.12 (11)C24—C25—C26—C210.38 (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—C34176.50 (9)
C2—C3—C4—C545.15 (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—C5171.84 (8)C66—C61—C62—C630.17 (15)
C2—C3—C31—C32−159.31 (8)C6—C61—C66—C65176.46 (9)
C4—C3—C31—C3275.97 (11)C62—C61—C66—C65−0.54 (15)
O4—C4—C5—C6132.23 (9)C61—C62—C63—C640.37 (16)
C3—C4—C5—C6−47.35 (11)C62—C63—C64—C65−0.55 (16)
C4—C5—C6—N154.81 (10)C63—C64—C65—C660.18 (16)
C4—C5—C6—C61176.51 (8)C64—C65—C66—C610.37 (16)
N1—C6—C61—C62−138.96 (9)
D—H···AD—HH···AD···AD—H···A
C6—H6···O4i1.002.593.2798 (11)126
C34—H34B···Cg1ii0.992.873.7809 (12)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C6—H6⋯O4i 1.002.593.2798 (11)126
C34—H34B⋯Cg1ii 0.992.873.7809 (12)154

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C61–C66 ring.

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  2 in total
  2 in total

1.  Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-butyl-2,6-bis-(4-fluoro-phen-yl)piperidin-4-one.

Authors:  K Anitha; S Sivakumar; R Arulraj; K Rajkumar; Manpreet Kaur; Jerry P Jasinski
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2020-04-09

2.  Crystal structures of two new 3-(2-chloro-eth-yl)-r(2),c(6)-diarylpiperidin-4-ones.

Authors:  K Rajkumar; S Sivakumar; R Arulraj; Manpreet Kaur; Jerry P Jasinski; A Manimekalai; A Thiruvalluvar
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-03-09
  2 in total

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