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organic compounds
3,5-Dibenzoyl-2,6-dimethyl-1-pentyl-4-pyridone
aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts and Sciences, Yüzüncü Yıl University TR-65080 Van, Turkey
*Correspondence e-mail: sgul@omu.edu.tr
In the 26H27NO3, a one-dimensional network of C—H⋯O hydrogen bonds and π-ring interactions is responsible for crystal stabilization. Intermolecular hydrogen bonds and C—H⋯ π interactions produce R22(10), R44(27) and R44(29) rings.
of the title compound, CRelated 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 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
|
Data collection
|
Refinement
|
|
Data collection: X-AREA (Stoe & Cie, 2002); cell 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
).
Supporting information
10.1107/S1600536809006667/xu2481sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809006667/xu2481Isup2.hkl
3-Acetyl-5-benzoyl-2-phenyl-6-methyl-4-pyrone (0.33 g, 1 mmol) and n-pentylamine derivative (0.23 ml, 2 mmol) were refluxed in ethanol for 36 h. The solvent was evaporated under reduced pressure to give an oily residue which was treated with ether and finally crystallized from ethanol. Yield 35%, mp 210°C.
All H atoms were placed in calculated positions and constrained to ride on their parents atoms, with C—H = 0.93–0.97 A° and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C). The
was not determined, Friedels pairs were merged.Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); 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).C26H27NO3 | F(000) = 856 |
Mr = 401.49 | Dx = 1.145 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5814 reflections |
a = 7.7879 (3) Å | θ = 1.6–26.8° |
b = 12.6502 (6) Å | µ = 0.07 mm−1 |
c = 23.6491 (14) Å | T = 296 K |
V = 2329.9 (2) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.34 × 0.16 mm |
Stoe IPDS-II diffractometer | 1239 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.096 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
Detector resolution: 6.67 pixels mm-1 | h = −9→9 |
ω scans | k = −15→14 |
10674 measured reflections | l = −27→29 |
2632 independent 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)] = 0.103 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.316 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
2632 reflections | (Δ/σ)max = 0.002 |
266 parameters | Δρmax = 0.44 e Å−3 |
1 restraint | Δρmin = −0.60 e Å−3 |
C26H27NO3 | V = 2329.9 (2) Å3 |
Mr = 401.49 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.7879 (3) Å | µ = 0.07 mm−1 |
b = 12.6502 (6) Å | T = 296 K |
c = 23.6491 (14) Å | 0.45 × 0.34 × 0.16 mm |
Stoe IPDS-II diffractometer | 1239 reflections with I > 2σ(I) |
10674 measured reflections | Rint = 0.096 |
2632 independent reflections |
R[F2 > 2σ(F2)] = 0.103 | 1 restraint |
wR(F2) = 0.316 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.44 e Å−3 |
2632 reflections | Δρmin = −0.60 e Å−3 |
266 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8305 (12) | 0.7239 (8) | 0.8563 (4) | 0.090 (3) | |
H1 | 0.8339 | 0.7864 | 0.8770 | 0.107* | |
C2 | 0.9313 (13) | 0.6404 (10) | 0.8730 (5) | 0.100 (3) | |
H2 | 1.0009 | 0.6460 | 0.9048 | 0.120* | |
C3 | 0.9274 (16) | 0.5502 (11) | 0.8425 (5) | 0.111 (4) | |
H3 | 0.9954 | 0.4932 | 0.8532 | 0.134* | |
C4 | 0.8278 (16) | 0.5426 (8) | 0.7976 (5) | 0.104 (3) | |
H4 | 0.8290 | 0.4798 | 0.7772 | 0.125* | |
C5 | 0.7240 (12) | 0.6216 (7) | 0.7797 (3) | 0.080 (2) | |
H5 | 0.6540 | 0.6124 | 0.7482 | 0.096* | |
C6 | 0.7237 (10) | 0.7178 (6) | 0.8093 (3) | 0.0649 (18) | |
C7 | 0.6137 (11) | 0.8055 (6) | 0.7925 (3) | 0.075 (2) | |
C8 | 0.5347 (9) | 0.8073 (5) | 0.7345 (3) | 0.0616 (17) | |
C9 | 0.6469 (10) | 0.8425 (6) | 0.6904 (3) | 0.0671 (19) | |
C10 | 0.5706 (11) | 0.8403 (6) | 0.6347 (4) | 0.077 (2) | |
C11 | 0.4073 (13) | 0.8064 (7) | 0.6266 (3) | 0.081 (2) | |
C12 | 0.3721 (10) | 0.7743 (6) | 0.7247 (3) | 0.072 (2) | |
C13 | 0.2594 (13) | 0.7343 (9) | 0.7728 (4) | 0.103 (3) | |
H13A | 0.3116 | 0.7518 | 0.8084 | 0.154* | |
H13B | 0.2472 | 0.6589 | 0.7700 | 0.154* | |
H13C | 0.1483 | 0.7668 | 0.7705 | 0.154* | |
C14 | 0.3253 (17) | 0.8085 (11) | 0.5670 (4) | 0.126 (4) | |
H14A | 0.2600 | 0.7451 | 0.5612 | 0.188* | |
H14B | 0.4142 | 0.8130 | 0.5389 | 0.188* | |
H14C | 0.2510 | 0.8688 | 0.5638 | 0.188* | |
C15 | 0.6801 (14) | 0.8736 (7) | 0.5869 (4) | 0.091 (3) | |
C16 | 0.6728 (10) | 0.9838 (6) | 0.5644 (3) | 0.071 (2) | |
C17 | 0.5731 (11) | 1.0598 (7) | 0.5895 (3) | 0.078 (2) | |
H17 | 0.5064 | 1.0438 | 0.6210 | 0.093* | |
C18 | 0.5739 (12) | 1.1613 (7) | 0.5668 (4) | 0.087 (2) | |
H18 | 0.5086 | 1.2137 | 0.5840 | 0.105* | |
C19 | 0.6669 (14) | 1.1856 (7) | 0.5204 (4) | 0.092 (3) | |
H19 | 0.6641 | 1.2536 | 0.5055 | 0.111* | |
C20 | 0.7670 (12) | 1.1074 (8) | 0.4953 (4) | 0.090 (3) | |
H20 | 0.8320 | 1.1230 | 0.4634 | 0.108* | |
C21 | 0.7700 (11) | 1.0099 (7) | 0.5170 (3) | 0.075 (2) | |
H21 | 0.8383 | 0.9585 | 0.5002 | 0.089* | |
C22 | 0.1361 (11) | 0.7219 (9) | 0.6621 (4) | 0.100 (3) | |
H22A | 0.0664 | 0.7320 | 0.6957 | 0.120* | |
H22B | 0.0783 | 0.7562 | 0.6308 | 0.120* | |
C23 | 0.1501 (16) | 0.6065 (10) | 0.6501 (6) | 0.130 (4) | |
H23A | 0.2191 | 0.5965 | 0.6163 | 0.156* | |
H23B | 0.2089 | 0.5724 | 0.6813 | 0.156* | |
C24 | −0.0144 (17) | 0.5563 (12) | 0.6419 (5) | 0.129 | |
H24A | 0.0008 | 0.4912 | 0.6630 | 0.155* | |
H24B | −0.0877 | 0.5995 | 0.6657 | 0.155* | |
C25 | −0.130 (2) | 0.5243 (14) | 0.5997 (7) | 0.175 | |
H25A | −0.0587 | 0.4664 | 0.5866 | 0.211* | |
H25B | −0.1008 | 0.5814 | 0.5741 | 0.211* | |
C26 | −0.281 (3) | 0.4911 (19) | 0.5675 (11) | 0.247 (9) | |
H26A | −0.3441 | 0.4394 | 0.5888 | 0.371* | |
H26B | −0.2452 | 0.4609 | 0.5322 | 0.371* | |
H26C | −0.3531 | 0.5512 | 0.5604 | 0.371* | |
N1 | 0.3069 (8) | 0.7731 (5) | 0.6710 (3) | 0.0749 (18) | |
O1 | 0.5886 (10) | 0.8785 (6) | 0.8250 (3) | 0.112 (2) | |
O2 | 0.7961 (8) | 0.8698 (6) | 0.6990 (3) | 0.103 (2) | |
O3 | 0.7820 (14) | 0.8093 (6) | 0.5670 (4) | 0.150 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.086 (6) | 0.104 (6) | 0.079 (5) | −0.018 (5) | 0.014 (5) | −0.007 (5) |
C2 | 0.079 (6) | 0.125 (9) | 0.094 (7) | 0.009 (6) | −0.003 (5) | 0.037 (6) |
C3 | 0.102 (8) | 0.119 (9) | 0.113 (9) | 0.021 (7) | 0.017 (7) | 0.034 (7) |
C4 | 0.132 (9) | 0.083 (6) | 0.098 (7) | 0.016 (6) | 0.015 (8) | −0.001 (5) |
C5 | 0.095 (6) | 0.073 (5) | 0.071 (5) | 0.008 (5) | 0.000 (5) | 0.011 (4) |
C6 | 0.066 (4) | 0.072 (4) | 0.056 (4) | −0.008 (4) | −0.005 (4) | 0.011 (3) |
C7 | 0.082 (5) | 0.064 (4) | 0.078 (5) | 0.001 (4) | 0.007 (4) | −0.003 (4) |
C8 | 0.061 (4) | 0.057 (4) | 0.066 (4) | −0.001 (3) | 0.003 (4) | 0.003 (3) |
C9 | 0.068 (5) | 0.065 (4) | 0.068 (5) | 0.004 (4) | 0.016 (4) | 0.008 (3) |
C10 | 0.080 (5) | 0.067 (4) | 0.084 (5) | 0.003 (4) | 0.008 (5) | 0.020 (4) |
C11 | 0.100 (6) | 0.081 (5) | 0.064 (4) | 0.022 (5) | −0.014 (5) | 0.014 (4) |
C12 | 0.068 (4) | 0.080 (5) | 0.068 (4) | 0.009 (4) | 0.018 (4) | 0.006 (4) |
C13 | 0.090 (6) | 0.121 (7) | 0.097 (6) | −0.032 (6) | 0.005 (5) | 0.016 (6) |
C14 | 0.141 (9) | 0.162 (11) | 0.074 (6) | 0.009 (9) | −0.022 (7) | 0.012 (6) |
C15 | 0.117 (7) | 0.082 (6) | 0.073 (5) | 0.019 (6) | 0.032 (5) | 0.015 (4) |
C16 | 0.074 (5) | 0.086 (5) | 0.053 (4) | −0.002 (4) | 0.001 (4) | 0.006 (4) |
C17 | 0.084 (5) | 0.088 (6) | 0.062 (4) | 0.007 (4) | 0.010 (4) | 0.007 (4) |
C18 | 0.097 (6) | 0.081 (5) | 0.084 (6) | 0.009 (5) | 0.009 (6) | 0.005 (5) |
C19 | 0.106 (7) | 0.076 (5) | 0.095 (6) | 0.003 (5) | −0.007 (6) | 0.012 (5) |
C20 | 0.089 (6) | 0.103 (6) | 0.078 (5) | −0.016 (6) | 0.016 (5) | 0.032 (5) |
C21 | 0.079 (5) | 0.080 (5) | 0.064 (4) | 0.001 (4) | 0.010 (4) | 0.008 (4) |
C22 | 0.061 (5) | 0.146 (9) | 0.093 (6) | 0.005 (6) | −0.020 (5) | 0.003 (6) |
C23 | 0.109 (8) | 0.114 (8) | 0.166 (11) | −0.020 (7) | −0.021 (8) | −0.029 (8) |
C24 | 0.128 | 0.155 | 0.104 | −0.031 (8) | 0.017 (7) | −0.036 (6) |
C25 | 0.175 | 0.155 | 0.197 | −0.001 (12) | 0.005 (14) | −0.030 (11) |
C26 | 0.180 | 0.30 (3) | 0.259 | −0.146 (16) | −0.002 (18) | −0.01 (2) |
N1 | 0.068 (4) | 0.077 (4) | 0.080 (4) | 0.004 (3) | −0.005 (4) | 0.011 (3) |
O1 | 0.134 (6) | 0.100 (5) | 0.102 (4) | 0.018 (5) | 0.001 (4) | −0.025 (4) |
O2 | 0.074 (4) | 0.118 (5) | 0.117 (5) | −0.020 (4) | 0.012 (4) | 0.014 (4) |
O3 | 0.213 (9) | 0.096 (5) | 0.141 (6) | 0.055 (6) | 0.088 (7) | 0.035 (4) |
C1—C2 | 1.374 (14) | C15—O3 | 1.230 (11) |
C1—C6 | 1.389 (11) | C15—C16 | 1.494 (12) |
C1—H1 | 0.9300 | C16—C17 | 1.370 (11) |
C2—C3 | 1.351 (16) | C16—C21 | 1.391 (11) |
C2—H2 | 0.9300 | C17—C18 | 1.392 (11) |
C3—C4 | 1.318 (15) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.349 (12) |
C4—C5 | 1.353 (13) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.394 (13) |
C5—C6 | 1.404 (11) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.335 (12) |
C6—C7 | 1.457 (11) | C20—H20 | 0.9300 |
C7—O1 | 1.217 (10) | C21—H21 | 0.9300 |
C7—C8 | 1.504 (11) | C22—C23 | 1.491 (17) |
C8—C12 | 1.354 (11) | C22—N1 | 1.494 (12) |
C8—C9 | 1.432 (10) | C22—H22A | 0.9700 |
C9—O2 | 1.229 (10) | C22—H22B | 0.9700 |
C9—C10 | 1.445 (12) | C23—C24 | 1.442 (16) |
C10—C11 | 1.356 (13) | C23—H23A | 0.9700 |
C10—C15 | 1.478 (12) | C23—H23B | 0.9700 |
C11—N1 | 1.374 (11) | C24—C25 | 1.404 (15) |
C11—C14 | 1.549 (13) | C24—H24A | 0.9700 |
C12—N1 | 1.368 (10) | C24—H24B | 0.9700 |
C12—C13 | 1.525 (11) | C25—C26 | 1.46 (2) |
C13—H13A | 0.9600 | C25—H25A | 0.9700 |
C13—H13B | 0.9600 | C25—H25B | 0.9700 |
C13—H13C | 0.9600 | C26—H26A | 0.9600 |
C14—H14A | 0.9600 | C26—H26B | 0.9600 |
C14—H14B | 0.9600 | C26—H26C | 0.9600 |
C14—H14C | 0.9600 | ||
C2—C1—C6 | 122.0 (9) | C17—C16—C21 | 119.4 (7) |
C2—C1—H1 | 119.0 | C17—C16—C15 | 121.5 (7) |
C6—C1—H1 | 119.0 | C21—C16—C15 | 119.1 (7) |
C3—C2—C1 | 118.8 (10) | C16—C17—C18 | 118.5 (8) |
C3—C2—H2 | 120.6 | C16—C17—H17 | 120.8 |
C1—C2—H2 | 120.6 | C18—C17—H17 | 120.8 |
C4—C3—C2 | 120.3 (11) | C19—C18—C17 | 121.8 (9) |
C4—C3—H3 | 119.8 | C19—C18—H18 | 119.1 |
C2—C3—H3 | 119.8 | C17—C18—H18 | 119.1 |
C3—C4—C5 | 123.4 (10) | C18—C19—C20 | 119.0 (8) |
C3—C4—H4 | 118.3 | C18—C19—H19 | 120.5 |
C5—C4—H4 | 118.3 | C20—C19—H19 | 120.5 |
C4—C5—C6 | 119.0 (8) | C21—C20—C19 | 120.1 (8) |
C4—C5—H5 | 120.5 | C21—C20—H20 | 120.0 |
C6—C5—H5 | 120.5 | C19—C20—H20 | 120.0 |
C1—C6—C5 | 116.5 (8) | C20—C21—C16 | 121.3 (8) |
C1—C6—C7 | 121.8 (7) | C20—C21—H21 | 119.4 |
C5—C6—C7 | 121.6 (7) | C16—C21—H21 | 119.4 |
O1—C7—C6 | 120.0 (8) | C23—C22—N1 | 112.7 (8) |
O1—C7—C8 | 119.9 (7) | C23—C22—H22A | 109.0 |
C6—C7—C8 | 120.0 (7) | N1—C22—H22A | 109.0 |
C12—C8—C9 | 122.7 (7) | C23—C22—H22B | 109.0 |
C12—C8—C7 | 122.4 (7) | N1—C22—H22B | 109.0 |
C9—C8—C7 | 114.8 (7) | H22A—C22—H22B | 107.8 |
O2—C9—C8 | 123.0 (8) | C24—C23—C22 | 113.1 (11) |
O2—C9—C10 | 123.0 (8) | C24—C23—H23A | 109.0 |
C8—C9—C10 | 114.1 (7) | C22—C23—H23A | 109.0 |
C11—C10—C9 | 121.3 (8) | C24—C23—H23B | 109.0 |
C11—C10—C15 | 121.6 (9) | C22—C23—H23B | 109.0 |
C9—C10—C15 | 117.1 (8) | H23A—C23—H23B | 107.8 |
C10—C11—N1 | 121.6 (7) | C25—C24—C23 | 142.3 (14) |
C10—C11—C14 | 120.6 (9) | C25—C24—H24A | 101.4 |
N1—C11—C14 | 117.8 (9) | C23—C24—H24A | 101.4 |
C8—C12—N1 | 120.7 (7) | C25—C24—H24B | 101.4 |
C8—C12—C13 | 120.8 (7) | C23—C24—H24B | 101.4 |
N1—C12—C13 | 118.4 (7) | H24A—C24—H24B | 104.6 |
C12—C13—H13A | 109.5 | C24—C25—C26 | 165.7 (17) |
C12—C13—H13B | 109.5 | C24—C25—H25A | 94.5 |
H13A—C13—H13B | 109.5 | C26—C25—H25A | 94.5 |
C12—C13—H13C | 109.5 | C24—C25—H25B | 94.4 |
H13A—C13—H13C | 109.5 | C26—C25—H25B | 94.5 |
H13B—C13—H13C | 109.5 | H25A—C25—H25B | 103.2 |
C11—C14—H14A | 109.5 | C25—C26—H26A | 109.5 |
C11—C14—H14B | 109.5 | C25—C26—H26B | 109.5 |
H14A—C14—H14B | 109.5 | H26A—C26—H26B | 109.5 |
C11—C14—H14C | 109.5 | C25—C26—H26C | 109.5 |
H14A—C14—H14C | 109.5 | H26A—C26—H26C | 109.5 |
H14B—C14—H14C | 109.5 | H26B—C26—H26C | 109.5 |
O3—C15—C10 | 118.5 (8) | C12—N1—C11 | 119.6 (7) |
O3—C15—C16 | 120.4 (8) | C12—N1—C22 | 117.8 (7) |
C10—C15—C16 | 121.1 (8) | C11—N1—C22 | 122.2 (7) |
C6—C1—C2—C3 | 0.7 (14) | C7—C8—C12—C13 | 0.7 (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—O3 | 81.2 (12) |
C3—C4—C5—C6 | 1.4 (15) | C11—C10—C15—C16 | 85.2 (11) |
C2—C1—C6—C5 | −0.1 (12) | C9—C10—C15—C16 | −96.6 (10) |
C2—C1—C6—C7 | 178.4 (8) | O3—C15—C16—C17 | −173.4 (10) |
C4—C5—C6—C1 | −0.9 (12) | C10—C15—C16—C17 | 4.3 (14) |
C4—C5—C6—C7 | −179.4 (8) | O3—C15—C16—C21 | 6.4 (15) |
C1—C6—C7—O1 | −13.8 (12) | C10—C15—C16—C21 | −175.9 (8) |
C5—C6—C7—O1 | 164.5 (8) | C21—C16—C17—C18 | −0.5 (12) |
C1—C6—C7—C8 | 164.6 (7) | C15—C16—C17—C18 | 179.2 (9) |
C5—C6—C7—C8 | −17.0 (11) | C16—C17—C18—C19 | 1.4 (14) |
O1—C7—C8—C12 | −84.2 (10) | C17—C18—C19—C20 | −1.2 (15) |
C6—C7—C8—C12 | 97.4 (9) | C18—C19—C20—C21 | 0.1 (15) |
O1—C7—C8—C9 | 98.2 (9) | C19—C20—C21—C16 | 0.7 (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—C20 | 179.7 (9) |
C7—C8—C9—O2 | −0.3 (11) | N1—C22—C23—C24 | 179.5 (10) |
C12—C8—C9—C10 | 0.4 (10) | C22—C23—C24—C25 | 96 (2) |
C7—C8—C9—C10 | 178.0 (6) | C23—C24—C25—C26 | −160 (7) |
O2—C9—C10—C11 | 177.8 (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—C22 | 171.7 (8) |
C8—C9—C10—C15 | −178.8 (7) | C13—C12—N1—C22 | −6.4 (11) |
C9—C10—C11—N1 | 0.2 (12) | C10—C11—N1—C12 | 0.3 (12) |
C15—C10—C11—N1 | 178.4 (8) | C14—C11—N1—C12 | −177.3 (9) |
C9—C10—C11—C14 | 177.7 (9) | C10—C11—N1—C22 | −171.5 (8) |
C15—C10—C11—C14 | −4.1 (13) | C14—C11—N1—C22 | 11.0 (12) |
C9—C8—C12—N1 | 0.1 (12) | C23—C22—N1—C12 | −88.7 (11) |
C7—C8—C12—N1 | −177.4 (7) | C23—C22—N1—C11 | 83.2 (12) |
C9—C8—C12—C13 | 178.1 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.57 | 3.288 (14) | 135 |
C2—H2···Cg3i | 0.93 | 2.95 | 3.759 (11) | 145 |
C17—H17···Cg2ii | 0.93 | 3.09 | 3.813 (9) | 135 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C26H27NO3 |
Mr | 401.49 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 7.7879 (3), 12.6502 (6), 23.6491 (14) |
V (Å3) | 2329.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.45 × 0.34 × 0.16 |
Data collection | |
Diffractometer | Stoe IPDS-II diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10674, 2632, 1239 |
Rint | 0.096 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.103, 0.316, 0.97 |
No. of reflections | 2632 |
No. of parameters | 266 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.60 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.57 | 3.288 (14) | 134.5 |
C2—H2···Cg3i | 0.93 | 2.95 | 3.759 (11) | 145 |
C17—H17···Cg2ii | 0.93 | 3.09 | 3.813 (9) | 135 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences of Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Grant of Ondokuz Mayıs University).
References
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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.
Six-membered nitrogen heterocycles are key units in medicinal chemistry and versatile intermediates in organic synthesis (Dong et al., 2005, and references therein). 4(1H)-pyridinones are of great importance for pharmacological reasons (Hershko et al., 1999). On the other hand, the reaction of primary amines with 4(1H)-pyrones to form 4(1H)-pyridinones have been known for more than 90 years (Peratoner, 1906). Both one step synthesis 3-acetyl-5-benzoyl-6-methyl-2-phenyl-4(1H)-pyrone derivative 1 (scheme 2) from the reaction of dibenzoylmethane with oxalyl chloride and the reactions of 1 with primary amines have been reported recently (Şener et al., 2007). These studies relieved that 1 could reacts with n-pentylamine even when it is accompanying with a rearrangement to give a pyridinone derivative 2 (Fig. 3) with symmetrical structure. Here, it has been planned to confirm this symmetrical structure of 2 by X-ray diffraction method.
The molecular structure and atom-numbering scheme is shown in Fig. 1; selected bond lengths are given in Table 1. The C7—O1, C9—O2 and C15—O3 bond lengths are indicative of a significant double-bond character, respectively (Table 1). The pyridine ring is twisted with C1- and C16-benzene rings with dihedral angles of 89.9 (3)° and 86.9 (3)°, respectively.
In the crystal structure the weak C—H···O hydrogen bonding occurs (Table 2), so forming a C(9)6 chain running parallel to the [010] direction (Fig. 2). The title compound also contains two intermolecular C—H···π interactions. The first is from C2 to the centroid of the C16ii-ring [symmetry code: (ii) 2-x,-1/2+y,3/2-z) [C2···Cg3 = 3.759 (11) Å, H2···Cg3 = 2.9516 Å, C2—H2···Cg3 = 145°]. The second C—H···π contact is from C17 to the centroid of the C1iii-ring [symmetry code: (iii) 1-x, 1/2+y, 3/2-z) [C17···Cg2 = 3.813 (9) Å, H17···Cg2= 3.0946 Å, C17—H17···Cg2 = 135°]. The combination of the C—H···π interactions along [010] generates a chain of edge-fused R44(27) rings. Intermolecular hydrogen bonds and C—H···π interactions produce R22(10) and R44(29) rings.