Literature DB >> 21582271

3,5-Dibenzoyl-2,6-dimethyl-1-pentyl-4-pyridone.

Zarife Sibel Sahin, Samil Işık, Ahmet Sener, Meltem Tan.   

Abstract

In the crystal structure of the title compound, C(26)H(27)NO(3), a one-dimensional network of C-H⋯O hydrogen bonds and π-ring inter-actions is responsible for crystal stabilization. Inter-molecular n class="Chemical">hydrogen bonds and C-H⋯ π inter-actions produce R(2) (2)(10), R(4) (4)(27) and R(4) (4)(29) rings.

Entities:  

Year:  2009        PMID： 21582271      PMCID： PMC2968478          DOI： 10.1107/S1600536809006667

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


Related literature

Six-membered nitro­gen heterocycles are key units in medicinal chemistry and versatile inter­mediates in organic synthesis, see: Dong et al. (2005 ▶) and references therein. 4(1H)-pyridinones are of great importance for pharmacological reasons, see: Hershko et al. (1999 ▶). The reaction of primary n class="Chemical">amines with 4(1H)-pyrones to form 4(1H)-pyridinones has been known for more than 90 years (Peratoner, 1906 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the reaction of dibenzoyl­methane with oxalyl chloride, see: Şener et al. (2007 ▶).

Experimental

Crystal data

C26H27NO3 M = 401.49 Orthorhombic, a = 7.7879 (3) Å b = 12.6502 (6) Å c = 23.6491 (14) Å V = 2329.9 (2) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.45 × 0.34 × 0.16 mm

Data collection

Stoe IPDS-II diffractometer Absorption correction: none 10674 measured reflections 2632 independent reflections 1239 reflections with I > 2σ(I) R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.103 wR(F 2) = 0.316 S = 0.97 2632 reflections 266 parameters 1 restraint H-atom parameters constrained Δρmax = 0.44 e Å−3 Δρmin = −0.60 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006667/xu2481sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006667/xu2481Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H27NO3F(000) = 856
Mr = 401.49Dx = 1.145 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5814 reflections
a = 7.7879 (3) Åθ = 1.6–26.8°
b = 12.6502 (6) ŵ = 0.07 mm−1
c = 23.6491 (14) ÅT = 296 K
V = 2329.9 (2) Å3Prism, colourless
Z = 40.45 × 0.34 × 0.16 mm
Stoe IPDS-II diffractometer1239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.096
graphiteθmax = 26.0°, θmin = 1.7°
Detector resolution: 6.67 pixels mm-1h = −9→9
ω scansk = −15→14
10674 measured reflectionsl = −27→29
2632 independent 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)] = 0.103Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.316H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2632 reflections(Δ/σ)max = 0.002
266 parametersΔρmax = 0.44 e Å−3
1 restraintΔρmin = −0.60 e Å−3
Experimental. Ir (KBr): (CH, aromatic) 3100, (CH, aliphatic) 2956–2928, (C=O) 1670, 1621 cm-1; 1H NMR (CDCl3): δ 7.90–7.26 (m, 10H, CH, aromatic), 3.98–3.85 (t, 2H, N—CH2–), 2.30 (s, 6H, CH3), 1.75–1.71 (m, 2H, N—CH2—CH2—CH2CH2CH3), 1.41–1.34 (m, 4H, N—CH2—CH2—CH2—CH2—CH3), 0.96–0.90 p.p.m. (t, 3H, N—CH2—CH2—CH2—CH2—CH3); 13C NMR (CDCl3): δ 198.47 (C=O, benzoyl), 175.68 (C=O, C-4), 148.58 (C-2 and C-6), 139.09, 135.44, 132.42, 131.33, 130.58, 50.20 (N—CH2–), 31.87 (CH3), 30.70 (N—CH2—CH2—CH2CH2CH3), 24.19 (N—CH2CH2—CH2—CH2CH3), 19.46 (N—CH2CH2CH2—CH2—CH3), 15.85 p.p.m. (N—CH2CH2CH2CH2—CH3). Anal. Calcd. for C26H21NO3: C, 78.97; H, 5.35; N, 3.54. Found: C, 78.91; H, 5.34; N, 3.55.
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.
xyzUiso*/Ueq
C10.8305 (12)0.7239 (8)0.8563 (4)0.090 (3)
H10.83390.78640.87700.107*
C20.9313 (13)0.6404 (10)0.8730 (5)0.100 (3)
H21.00090.64600.90480.120*
C30.9274 (16)0.5502 (11)0.8425 (5)0.111 (4)
H30.99540.49320.85320.134*
C40.8278 (16)0.5426 (8)0.7976 (5)0.104 (3)
H40.82900.47980.77720.125*
C50.7240 (12)0.6216 (7)0.7797 (3)0.080 (2)
H50.65400.61240.74820.096*
C60.7237 (10)0.7178 (6)0.8093 (3)0.0649 (18)
C70.6137 (11)0.8055 (6)0.7925 (3)0.075 (2)
C80.5347 (9)0.8073 (5)0.7345 (3)0.0616 (17)
C90.6469 (10)0.8425 (6)0.6904 (3)0.0671 (19)
C100.5706 (11)0.8403 (6)0.6347 (4)0.077 (2)
C110.4073 (13)0.8064 (7)0.6266 (3)0.081 (2)
C120.3721 (10)0.7743 (6)0.7247 (3)0.072 (2)
C130.2594 (13)0.7343 (9)0.7728 (4)0.103 (3)
H13A0.31160.75180.80840.154*
H13B0.24720.65890.77000.154*
H13C0.14830.76680.77050.154*
C140.3253 (17)0.8085 (11)0.5670 (4)0.126 (4)
H14A0.26000.74510.56120.188*
H14B0.41420.81300.53890.188*
H14C0.25100.86880.56380.188*
C150.6801 (14)0.8736 (7)0.5869 (4)0.091 (3)
C160.6728 (10)0.9838 (6)0.5644 (3)0.071 (2)
C170.5731 (11)1.0598 (7)0.5895 (3)0.078 (2)
H170.50641.04380.62100.093*
C180.5739 (12)1.1613 (7)0.5668 (4)0.087 (2)
H180.50861.21370.58400.105*
C190.6669 (14)1.1856 (7)0.5204 (4)0.092 (3)
H190.66411.25360.50550.111*
C200.7670 (12)1.1074 (8)0.4953 (4)0.090 (3)
H200.83201.12300.46340.108*
C210.7700 (11)1.0099 (7)0.5170 (3)0.075 (2)
H210.83830.95850.50020.089*
C220.1361 (11)0.7219 (9)0.6621 (4)0.100 (3)
H22A0.06640.73200.69570.120*
H22B0.07830.75620.63080.120*
C230.1501 (16)0.6065 (10)0.6501 (6)0.130 (4)
H23A0.21910.59650.61630.156*
H23B0.20890.57240.68130.156*
C24−0.0144 (17)0.5563 (12)0.6419 (5)0.129
H24A0.00080.49120.66300.155*
H24B−0.08770.59950.66570.155*
C25−0.130 (2)0.5243 (14)0.5997 (7)0.175
H25A−0.05870.46640.58660.211*
H25B−0.10080.58140.57410.211*
C26−0.281 (3)0.4911 (19)0.5675 (11)0.247 (9)
H26A−0.34410.43940.58880.371*
H26B−0.24520.46090.53220.371*
H26C−0.35310.55120.56040.371*
N10.3069 (8)0.7731 (5)0.6710 (3)0.0749 (18)
O10.5886 (10)0.8785 (6)0.8250 (3)0.112 (2)
O20.7961 (8)0.8698 (6)0.6990 (3)0.103 (2)
O30.7820 (14)0.8093 (6)0.5670 (4)0.150 (4)
U11U22U33U12U13U23
C10.086 (6)0.104 (6)0.079 (5)−0.018 (5)0.014 (5)−0.007 (5)
C20.079 (6)0.125 (9)0.094 (7)0.009 (6)−0.003 (5)0.037 (6)
C30.102 (8)0.119 (9)0.113 (9)0.021 (7)0.017 (7)0.034 (7)
C40.132 (9)0.083 (6)0.098 (7)0.016 (6)0.015 (8)−0.001 (5)
C50.095 (6)0.073 (5)0.071 (5)0.008 (5)0.000 (5)0.011 (4)
C60.066 (4)0.072 (4)0.056 (4)−0.008 (4)−0.005 (4)0.011 (3)
C70.082 (5)0.064 (4)0.078 (5)0.001 (4)0.007 (4)−0.003 (4)
C80.061 (4)0.057 (4)0.066 (4)−0.001 (3)0.003 (4)0.003 (3)
C90.068 (5)0.065 (4)0.068 (5)0.004 (4)0.016 (4)0.008 (3)
C100.080 (5)0.067 (4)0.084 (5)0.003 (4)0.008 (5)0.020 (4)
C110.100 (6)0.081 (5)0.064 (4)0.022 (5)−0.014 (5)0.014 (4)
C120.068 (4)0.080 (5)0.068 (4)0.009 (4)0.018 (4)0.006 (4)
C130.090 (6)0.121 (7)0.097 (6)−0.032 (6)0.005 (5)0.016 (6)
C140.141 (9)0.162 (11)0.074 (6)0.009 (9)−0.022 (7)0.012 (6)
C150.117 (7)0.082 (6)0.073 (5)0.019 (6)0.032 (5)0.015 (4)
C160.074 (5)0.086 (5)0.053 (4)−0.002 (4)0.001 (4)0.006 (4)
C170.084 (5)0.088 (6)0.062 (4)0.007 (4)0.010 (4)0.007 (4)
C180.097 (6)0.081 (5)0.084 (6)0.009 (5)0.009 (6)0.005 (5)
C190.106 (7)0.076 (5)0.095 (6)0.003 (5)−0.007 (6)0.012 (5)
C200.089 (6)0.103 (6)0.078 (5)−0.016 (6)0.016 (5)0.032 (5)
C210.079 (5)0.080 (5)0.064 (4)0.001 (4)0.010 (4)0.008 (4)
C220.061 (5)0.146 (9)0.093 (6)0.005 (6)−0.020 (5)0.003 (6)
C230.109 (8)0.114 (8)0.166 (11)−0.020 (7)−0.021 (8)−0.029 (8)
C240.1280.1550.104−0.031 (8)0.017 (7)−0.036 (6)
C250.1750.1550.197−0.001 (12)0.005 (14)−0.030 (11)
C260.1800.30 (3)0.259−0.146 (16)−0.002 (18)−0.01 (2)
N10.068 (4)0.077 (4)0.080 (4)0.004 (3)−0.005 (4)0.011 (3)
O10.134 (6)0.100 (5)0.102 (4)0.018 (5)0.001 (4)−0.025 (4)
O20.074 (4)0.118 (5)0.117 (5)−0.020 (4)0.012 (4)0.014 (4)
O30.213 (9)0.096 (5)0.141 (6)0.055 (6)0.088 (7)0.035 (4)
C1—C21.374 (14)C15—O31.230 (11)
C1—C61.389 (11)C15—C161.494 (12)
C1—H10.9300C16—C171.370 (11)
C2—C31.351 (16)C16—C211.391 (11)
C2—H20.9300C17—C181.392 (11)
C3—C41.318 (15)C17—H170.9300
C3—H30.9300C18—C191.349 (12)
C4—C51.353 (13)C18—H180.9300
C4—H40.9300C19—C201.394 (13)
C5—C61.404 (11)C19—H190.9300
C5—H50.9300C20—C211.335 (12)
C6—C71.457 (11)C20—H200.9300
C7—O11.217 (10)C21—H210.9300
C7—C81.504 (11)C22—C231.491 (17)
C8—C121.354 (11)C22—N11.494 (12)
C8—C91.432 (10)C22—H22A0.9700
C9—O21.229 (10)C22—H22B0.9700
C9—C101.445 (12)C23—C241.442 (16)
C10—C111.356 (13)C23—H23A0.9700
C10—C151.478 (12)C23—H23B0.9700
C11—N11.374 (11)C24—C251.404 (15)
C11—C141.549 (13)C24—H24A0.9700
C12—N11.368 (10)C24—H24B0.9700
C12—C131.525 (11)C25—C261.46 (2)
C13—H13A0.9600C25—H25A0.9700
C13—H13B0.9600C25—H25B0.9700
C13—H13C0.9600C26—H26A0.9600
C14—H14A0.9600C26—H26B0.9600
C14—H14B0.9600C26—H26C0.9600
C14—H14C0.9600
C2—C1—C6122.0 (9)C17—C16—C21119.4 (7)
C2—C1—H1119.0C17—C16—C15121.5 (7)
C6—C1—H1119.0C21—C16—C15119.1 (7)
C3—C2—C1118.8 (10)C16—C17—C18118.5 (8)
C3—C2—H2120.6C16—C17—H17120.8
C1—C2—H2120.6C18—C17—H17120.8
C4—C3—C2120.3 (11)C19—C18—C17121.8 (9)
C4—C3—H3119.8C19—C18—H18119.1
C2—C3—H3119.8C17—C18—H18119.1
C3—C4—C5123.4 (10)C18—C19—C20119.0 (8)
C3—C4—H4118.3C18—C19—H19120.5
C5—C4—H4118.3C20—C19—H19120.5
C4—C5—C6119.0 (8)C21—C20—C19120.1 (8)
C4—C5—H5120.5C21—C20—H20120.0
C6—C5—H5120.5C19—C20—H20120.0
C1—C6—C5116.5 (8)C20—C21—C16121.3 (8)
C1—C6—C7121.8 (7)C20—C21—H21119.4
C5—C6—C7121.6 (7)C16—C21—H21119.4
O1—C7—C6120.0 (8)C23—C22—N1112.7 (8)
O1—C7—C8119.9 (7)C23—C22—H22A109.0
C6—C7—C8120.0 (7)N1—C22—H22A109.0
C12—C8—C9122.7 (7)C23—C22—H22B109.0
C12—C8—C7122.4 (7)N1—C22—H22B109.0
C9—C8—C7114.8 (7)H22A—C22—H22B107.8
O2—C9—C8123.0 (8)C24—C23—C22113.1 (11)
O2—C9—C10123.0 (8)C24—C23—H23A109.0
C8—C9—C10114.1 (7)C22—C23—H23A109.0
C11—C10—C9121.3 (8)C24—C23—H23B109.0
C11—C10—C15121.6 (9)C22—C23—H23B109.0
C9—C10—C15117.1 (8)H23A—C23—H23B107.8
C10—C11—N1121.6 (7)C25—C24—C23142.3 (14)
C10—C11—C14120.6 (9)C25—C24—H24A101.4
N1—C11—C14117.8 (9)C23—C24—H24A101.4
C8—C12—N1120.7 (7)C25—C24—H24B101.4
C8—C12—C13120.8 (7)C23—C24—H24B101.4
N1—C12—C13118.4 (7)H24A—C24—H24B104.6
C12—C13—H13A109.5C24—C25—C26165.7 (17)
C12—C13—H13B109.5C24—C25—H25A94.5
H13A—C13—H13B109.5C26—C25—H25A94.5
C12—C13—H13C109.5C24—C25—H25B94.4
H13A—C13—H13C109.5C26—C25—H25B94.5
H13B—C13—H13C109.5H25A—C25—H25B103.2
C11—C14—H14A109.5C25—C26—H26A109.5
C11—C14—H14B109.5C25—C26—H26B109.5
H14A—C14—H14B109.5H26A—C26—H26B109.5
C11—C14—H14C109.5C25—C26—H26C109.5
H14A—C14—H14C109.5H26A—C26—H26C109.5
H14B—C14—H14C109.5H26B—C26—H26C109.5
O3—C15—C10118.5 (8)C12—N1—C11119.6 (7)
O3—C15—C16120.4 (8)C12—N1—C22117.8 (7)
C10—C15—C16121.1 (8)C11—N1—C22122.2 (7)
C6—C1—C2—C30.7 (14)C7—C8—C12—C130.7 (12)
C1—C2—C3—C4−0.3 (16)C11—C10—C15—O3−97.1 (13)
C2—C3—C4—C5−0.7 (17)C9—C10—C15—O381.2 (12)
C3—C4—C5—C61.4 (15)C11—C10—C15—C1685.2 (11)
C2—C1—C6—C5−0.1 (12)C9—C10—C15—C16−96.6 (10)
C2—C1—C6—C7178.4 (8)O3—C15—C16—C17−173.4 (10)
C4—C5—C6—C1−0.9 (12)C10—C15—C16—C174.3 (14)
C4—C5—C6—C7−179.4 (8)O3—C15—C16—C216.4 (15)
C1—C6—C7—O1−13.8 (12)C10—C15—C16—C21−175.9 (8)
C5—C6—C7—O1164.5 (8)C21—C16—C17—C18−0.5 (12)
C1—C6—C7—C8164.6 (7)C15—C16—C17—C18179.2 (9)
C5—C6—C7—C8−17.0 (11)C16—C17—C18—C191.4 (14)
O1—C7—C8—C12−84.2 (10)C17—C18—C19—C20−1.2 (15)
C6—C7—C8—C1297.4 (9)C18—C19—C20—C210.1 (15)
O1—C7—C8—C998.2 (9)C19—C20—C21—C160.7 (14)
C6—C7—C8—C9−80.2 (9)C17—C16—C21—C20−0.5 (13)
C12—C8—C9—O2−177.9 (8)C15—C16—C21—C20179.7 (9)
C7—C8—C9—O2−0.3 (11)N1—C22—C23—C24179.5 (10)
C12—C8—C9—C100.4 (10)C22—C23—C24—C2596 (2)
C7—C8—C9—C10178.0 (6)C23—C24—C25—C26−160 (7)
O2—C9—C10—C11177.8 (8)C8—C12—N1—C11−0.4 (11)
C8—C9—C10—C11−0.5 (11)C13—C12—N1—C11−178.5 (8)
O2—C9—C10—C15−0.5 (12)C8—C12—N1—C22171.7 (8)
C8—C9—C10—C15−178.8 (7)C13—C12—N1—C22−6.4 (11)
C9—C10—C11—N10.2 (12)C10—C11—N1—C120.3 (12)
C15—C10—C11—N1178.4 (8)C14—C11—N1—C12−177.3 (9)
C9—C10—C11—C14177.7 (9)C10—C11—N1—C22−171.5 (8)
C15—C10—C11—C14−4.1 (13)C14—C11—N1—C2211.0 (12)
C9—C8—C12—N10.1 (12)C23—C22—N1—C12−88.7 (11)
C7—C8—C12—N1−177.4 (7)C23—C22—N1—C1183.2 (12)
C9—C8—C12—C13178.1 (8)
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.573.288 (14)135
C2—H2···Cg3i0.932.953.759 (11)145
C17—H17···Cg2ii0.933.093.813 (9)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯O2i0.932.573.288 (14)135
C2—H2⋯Cg3ii0.932.953.759 (11)145
C17—H17⋯Cg2iii0.933.093.813 (9)135

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of the C1–C6 and C16–C21 rings, respectively.

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Journal:  Chem Commun (Camb)       Date:  2005-06-15       Impact factor: 6.222

3.  New 4(1H)-pyridinone derivatives as analgesic agents.

Authors:  M D Aytemir; T Uzbay; D D Erol
Journal:  Arzneimittelforschung       Date:  1999-03
  3 in total

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