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

Şahin, Z.S.; Işık, Ş.; Şener, A.; Tan, M.

doi:10.1107/S1600536809006667

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o619

doi:10.1107/S1600536809006667

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

Zarife Sibel Şahin,^a ^* Şamil Işık,^a Ahmet Şener ^b and Meltem Tan ^b

^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

(Received 30 January 2009; accepted 23 February 2009; online 28 February 2009)

In the crystal structure of the title compound, C₂₆H₂₇NO₃, 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.

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 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_r = 401.49
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.103
wR(F²) = 0.316
S = 0.97
2632 reflections
266 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯Cg3ⁱⁱ	0.93	2.95	3.759 (11)	145
C17—H17⋯Cg2ⁱⁱⁱ	0.93	3.09	3.813 (9)	135
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg2 and Cg3 are the centroids of the C1–C6 and C16–C21 rings, respectively.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006667/xu2481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006667/xu2481Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 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).Cg2 and Cg3 are the centroids of the C1–C6 and C16–C21 rings, respectively.

Experimental top

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.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability.
	Fig. 2. A part of the crystal structure of the title compound showing the R₂²(10) chain of rings along [010] generated by one C—H···O hydrogen bond and one C—H···π interaction.
	Fig. 3. Preparation of the title compound.

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

Crystal data top

C₂₆H₂₇NO₃	F(000) = 856
M_r = 401.49	D_x = 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

Data collection top

Stoe IPDS-II diffractometer	1239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.096
Graphite monochromator	θ_max = 26.0°, θ_min = 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 top

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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
2632 reflections	(Δ/σ)_max = 0.002
266 parameters	Δρ_max = 0.44 e Å⁻³
1 restraint	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₂₆H₂₇NO₃	V = 2329.9 (2) Å³
M_r = 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

Data collection top

Stoe IPDS-II diffractometer	1239 reflections with I > 2σ(I)
10674 measured reflections	R_int = 0.096
2632 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.103	1 restraint
wR(F²) = 0.316	H-atom parameters constrained
S = 0.97	Δρ_max = 0.44 e Å⁻³
2632 reflections	Δρ_min = −0.60 e Å⁻³
266 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Selected bond lengths (Å) top

C7—O1	1.217 (10)	C15—O3	1.230 (11)
C9—O2	1.229 (10)

Hydrogen-bond geometry (Å, º) top

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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