Dimethyl cis-2-methyl-3-p-tolyl­isoxazolidine-4,5-dicarboxyl­ate

Odabaşoğlu, M.; Özkan, H.; Yıldırır, Y.; Büyükgüngör, O.

doi:10.1107/S1600536809009350

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o806-o807

doi:10.1107/S1600536809009350

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Dimethyl cis-2-methyl-3-p-tolylisoxazolidine-4,5-dicarboxylate

Mustafa Odabaşoğlu,^a Hamdi Özkan,^b Yılmaz Yıldırır ^b and Orhan Büyükgüngör ^c ^*

^aPamukkale University, Denizli Higher Vocational School, Chemistry Program, Tr-20159 Kınıklı, Denizli, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Science, Gazi University, Ankara, Turkey, and ^cDepartment of Physics, Faculty of Arts and Science, Ondokuz Mayıs University, TR-55139 Kurupelit, Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 26 February 2009; accepted 13 March 2009; online 19 March 2009)

In the molecule of the title compound, C₁₅H₁₉NO₅, the isoxazole ring adopts an envelope conformation. In the crystal structure, weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules, in which they may be effective in the stabilization of the structure.

Related literature

For general background, see: Tufariello (1984 ); Villamena & Zweier (2004 ); Halliwell (2001a ,b ); Zweier & Talukder (2006 ); Janzen (1971 , 1980 ); Janzen & Haire (1990 ); Villamena et al. (2007 ); Floyd & Hensley (2000 ); Inanami & Kuwabara (1995 ); Becker et al. (2002 ). For bond-length data, see: Allen et al. (1987 ). For the preparation of N-Methyl-C-(-4-methylphenyl) nitrone, used in the synthesis, see: Heaney et al. (2001 ). For 1,3-dipolar cycloaddition of nitrones and alkenes, see: Confalone & Huie (1988 ); Torssell (1988 ); Frederickson (1997 ); Gothelf & Jorgensen (1998 ).

Experimental

Crystal data

C₁₅H₁₉NO₅
M_r = 293.31
Orthorhombic, C c c 2
a = 15.3832 (7) Å
b = 19.7959 (8) Å
c = 9.9612 (3) Å
V = 3033.4 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.78 × 0.45 × 0.27 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.973, T_max = 0.989
11187 measured reflections
1672 independent reflections
1554 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.074
S = 1.07
1672 reflections
192 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.93	2.60	3.300 (2)	133
C6—H6⋯O2ⁱⁱ	0.93	2.44	3.312 (3)	157
C9—H9⋯N1ⁱⁱ	0.98	2.55	3.497 (2)	162
C10—H10⋯O5ⁱⁱ	0.98	2.66	3.481 (2)	142
C15—H15a⋯O4ⁱⁱⁱ	0.96	2.64	3.403 (3)	137
Symmetry codes: (i) $[-x+1, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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/S1600536809009350/hk2635sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009350/hk2635Isup2.hkl

checkCIF report

Comment top

Nitrones are members of a class of compounds which are commonly used as precursors in the syntheses of natural products (Tufariello, 1984), as spin-trapping reagents in the identification of transient radicals (Villamena & Zweier, 2004), and as therapeutic agents (Floyd & Hensley, 2000; Inanami & Kuwabara, 1995) such as in the case of disodium-[(tert-butylimino) -methyl]benzene-1,3-disulfonate N-oxide (NXY-059) which is in clinical trials in the USA for the treatment of neurodegenerative disease (Becker et al., 2002). In recent years, it has become clear that reactive oxygen species (ROS) (e.g., radicals: O₂.^-, HO., HO₂., RO₂., RO., CO₃.^-, and CO₂.^-; and non-radicals such as H₂O₂, HOCl, O₃, ¹O₂, and ROOH) are critical mediators in cardiovascular dysfunction, neurodegenerative diseases, oncogenesis, lung damage and aging, to name a few (Halliwell, 2001a; 2001b; Zweier & Talukder, 2006). Electron paramagnetic resonance (EPR) spectroscopy has been an indispensable tool for the detection of these ROS via spin trapping [Villamena & Zweier, 2004; Janzen, 1971; Janzen,1980; Janzen & Haire, 1990; Villamena et al., 2007). The nitrone-based spin traps, 5,5-dimethyl-1-pyrroline N-oxide (DMPO), 5-diethoxyphosphoryl-5- methyl-pyrroline N-oxide (DEPMPO) and 5-ethoxycarbonyl-5-methyl-pyrroline N-oxide (EMPO), are the most commonly used spin-trapping reagents and have contributed significantly to the understanding of important free radical- mediated processes in chemical, biochemical, and biological systems in spite of their many limitations. The 1,3-dipolar cycloaddition of nitrones and alkenes is a powerful synthetic device that allows up to three new stereogenic centers to be assembled in a stereospecific manner in a single step (Confalone & Huie, 1988; Torssell, 1988; Frederickson, 1997; Gothelf & Jorgensen, 1998). The syntheses of isoxazolidine derivatives is an important subject in organic chemistry because they are found in the structure of most natural compounds and drugs. In recent years, isoxazolidine derivatives have been synthesized in high yield via intermolecular cycloaddition of N-methylnitrone with disubstituted olefins and are employed for biological evaluation. In view of the importance of the isoxazolidines, we report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is, of course, planar, while ring B (O1/N1/C8-C10) adopts envelope conformation with N1 atom displaced by 0.676 (3) Å from the plane of the other ring atoms.

In the crystal structure, weak intermolecular C-H···O and C-H···N hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Tufariello (1984); Villamena & Zweier (2004); Floyd & Hensley (2000); Inanami & Kuwabara (1995); Becker et al. (2002); Halliwell (2001a,b); Zweier & Talukder (2006); Janzen (1971); Janzen (1980); Janzen & Haire (1990); Villamena et al. (2007); Confalone & Huie (1988); Torssell (1988); Frederickson (1997); Gothelf & Jorgensen (1998). For related literature, see: Allen et al. (1987); Heaney et al. (2001).

Experimental top

N-Methyl-C-(-4-methylphenyl) nitrone, was prepared from 4-methyl benzaldehyde, N-methyl-hydroxylamine hydrochloride and sodium carbonate in CH₂Cl₂ according to the literature method (Heaney et al., 2001). For the preparation of the title compound, N-methyl-C-(-4-methylphenyl) nitrone (453 mg, 3 mmol) and dimethylmaleate (475 mg, 3,3 mmol) were dissolved in benzene (50 ml). The reaction mixture was refluxed for 9 h, and monitored by TLC. After evaporation of the solvent, the reaction mixture was separated by column chromatography, using the mixture of hexane/ethyl acetate (1:1) as the eluant. The cis-isomer, was recrystallized from CHCl₃/hexane (1:3) in 2 d (m.p. 371-372 K).

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 molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Dimethyl cis-2-methyl-3-p-tolylisoxazolidine-4,5-dicarboxylate top

Crystal data top

C₁₅H₁₉NO₅	F(000) = 1248
M_r = 293.31	D_x = 1.285 Mg m⁻³
Orthorhombic, Ccc2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2 -2c	Cell parameters from 11187 reflections
a = 15.3832 (7) Å	θ = 1.7–28.0°
b = 19.7959 (8) Å	µ = 0.10 mm⁻¹
c = 9.9612 (3) Å	T = 296 K
V = 3033.4 (2) Å³	Prism, colorless
Z = 8	0.78 × 0.45 × 0.27 mm

Data collection top

Stoe IPDS-2 diffractometer	1672 independent reflections
Radiation source: sealed X-ray tube	1554 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.026
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.7°
ω scan rotation method	h = −18→19
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
T_min = 0.973, T_max = 0.989	l = −12→12
11187 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0483P)² + 0.1649P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1672 reflections	Δρ_max = 0.11 e Å⁻³
192 parameters	Δρ_min = −0.10 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (3)

Crystal data top

C₁₅H₁₉NO₅	V = 3033.4 (2) Å³
M_r = 293.31	Z = 8
Orthorhombic, Ccc2	Mo Kα radiation
a = 15.3832 (7) Å	µ = 0.10 mm⁻¹
b = 19.7959 (8) Å	T = 296 K
c = 9.9612 (3) Å	0.78 × 0.45 × 0.27 mm

Data collection top

Stoe IPDS-2 diffractometer	1672 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1554 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.989	R_int = 0.026
11187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 0.11 e Å⁻³
1672 reflections	Δρ_min = −0.10 e Å⁻³
192 parameters

Special details top

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
O1	0.43759 (8)	0.40270 (6)	0.68227 (16)	0.0583 (4)
O2	0.61162 (9)	0.28606 (7)	0.63405 (15)	0.0577 (3)
O3	0.60989 (9)	0.22965 (7)	0.82785 (15)	0.0585 (3)
O4	0.66458 (9)	0.42093 (7)	0.75011 (16)	0.0626 (4)
O5	0.58517 (8)	0.43642 (7)	0.56403 (14)	0.0578 (3)
N1	0.41179 (9)	0.33370 (7)	0.64475 (16)	0.0485 (3)
C1	0.41288 (11)	0.22248 (9)	0.75835 (19)	0.0465 (4)
C2	0.43264 (13)	0.18797 (10)	0.6418 (2)	0.0555 (4)
H2	0.4530	0.2114	0.5672	0.067*
C3	0.42216 (14)	0.11819 (11)	0.6357 (3)	0.0647 (5)
H3	0.4352	0.0958	0.5561	0.078*
C4	0.39317 (13)	0.08153 (10)	0.7437 (3)	0.0650 (6)
C5	0.37474 (15)	0.11654 (12)	0.8606 (3)	0.0680 (6)
H5	0.3561	0.0928	0.9358	0.082*
C6	0.38338 (14)	0.18582 (11)	0.8680 (2)	0.0598 (5)
H6	0.3693	0.2081	0.9472	0.072*
C7	0.37937 (18)	0.00580 (14)	0.7372 (5)	0.0968 (10)
H7A	0.3207	−0.0046	0.7626	0.145*
H7B	0.4189	−0.0162	0.7975	0.145*
H7C	0.3897	−0.0097	0.6472	0.145*
C8	0.42456 (11)	0.29783 (9)	0.77189 (18)	0.0460 (4)
H8	0.3825	0.3149	0.8376	0.055*
C9	0.51660 (11)	0.32237 (8)	0.81227 (17)	0.0459 (4)
H9	0.5235	0.3215	0.9101	0.055*
C10	0.51412 (11)	0.39570 (8)	0.76058 (19)	0.0494 (4)
H10	0.5071	0.4249	0.8393	0.059*
C11	0.32106 (12)	0.33992 (12)	0.6060 (3)	0.0650 (5)
H11A	0.3171	0.3638	0.5223	0.097*
H11B	0.2900	0.3644	0.6740	0.097*
H11C	0.2962	0.2957	0.5960	0.097*
C12	0.58471 (11)	0.27910 (8)	0.74591 (19)	0.0461 (4)
C13	0.66586 (15)	0.17845 (11)	0.7714 (3)	0.0746 (6)
H13A	0.6799	0.1458	0.8392	0.112*
H13B	0.7183	0.1991	0.7392	0.112*
H13C	0.6366	0.1565	0.6984	0.112*
C14	0.59637 (11)	0.41814 (8)	0.6902 (2)	0.0475 (4)
C15	0.66179 (16)	0.46013 (14)	0.4967 (3)	0.0802 (7)
H15A	0.6475	0.4723	0.4060	0.120*
H15B	0.7049	0.4250	0.4960	0.120*
H15C	0.6843	0.4989	0.5429	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0479 (6)	0.0423 (6)	0.0848 (10)	0.0013 (5)	−0.0049 (6)	0.0057 (7)
O2	0.0693 (8)	0.0515 (7)	0.0524 (7)	0.0065 (6)	0.0100 (7)	−0.0007 (6)
O3	0.0641 (8)	0.0521 (7)	0.0592 (8)	0.0095 (6)	−0.0029 (7)	0.0078 (6)
O4	0.0535 (7)	0.0669 (8)	0.0674 (8)	−0.0085 (6)	−0.0091 (6)	−0.0009 (7)
O5	0.0556 (7)	0.0574 (8)	0.0606 (8)	−0.0062 (6)	−0.0025 (6)	0.0096 (6)
N1	0.0461 (7)	0.0452 (7)	0.0541 (9)	−0.0016 (5)	−0.0002 (6)	0.0047 (7)
C1	0.0465 (8)	0.0466 (8)	0.0465 (9)	−0.0038 (6)	−0.0023 (7)	0.0022 (8)
C2	0.0653 (11)	0.0513 (9)	0.0500 (9)	−0.0020 (8)	0.0027 (9)	−0.0002 (9)
C3	0.0672 (11)	0.0546 (11)	0.0724 (13)	−0.0016 (9)	−0.0039 (11)	−0.0135 (11)
C4	0.0526 (10)	0.0491 (10)	0.0935 (16)	−0.0068 (7)	−0.0156 (10)	0.0032 (11)
C5	0.0703 (13)	0.0613 (12)	0.0725 (13)	−0.0159 (10)	−0.0026 (11)	0.0182 (11)
C6	0.0674 (12)	0.0619 (11)	0.0500 (9)	−0.0133 (9)	0.0033 (9)	0.0035 (9)
C7	0.0854 (15)	0.0517 (11)	0.153 (3)	−0.0127 (11)	−0.0152 (19)	−0.0036 (16)
C8	0.0474 (8)	0.0463 (9)	0.0442 (8)	−0.0017 (6)	0.0061 (7)	−0.0014 (7)
C9	0.0532 (9)	0.0448 (8)	0.0398 (8)	−0.0009 (7)	0.0006 (7)	−0.0031 (7)
C10	0.0517 (9)	0.0423 (8)	0.0541 (9)	0.0011 (6)	0.0027 (8)	−0.0073 (8)
C11	0.0483 (9)	0.0661 (12)	0.0806 (14)	−0.0008 (8)	−0.0074 (10)	0.0108 (10)
C12	0.0479 (8)	0.0416 (8)	0.0489 (9)	−0.0023 (6)	−0.0026 (8)	−0.0011 (8)
C13	0.0717 (13)	0.0527 (11)	0.0995 (18)	0.0172 (9)	−0.0032 (13)	0.0027 (12)
C14	0.0491 (9)	0.0384 (7)	0.0549 (9)	−0.0022 (6)	−0.0027 (8)	−0.0046 (8)
C15	0.0757 (14)	0.0924 (16)	0.0726 (15)	−0.0240 (12)	0.0079 (12)	0.0166 (14)

Geometric parameters (Å, º) top

C1—C2	1.381 (3)	C10—O1	1.419 (2)
C1—C6	1.387 (3)	C10—C14	1.513 (3)
C1—C8	1.508 (2)	C10—H10	0.9800
C2—C3	1.392 (3)	C11—N1	1.453 (2)
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.373 (4)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.384 (4)	C12—O2	1.197 (2)
C4—C7	1.515 (3)	C12—O3	1.332 (2)
C5—C6	1.380 (3)	C13—O3	1.444 (3)
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—H7A	0.9600	C13—H13C	0.9600
C7—H7B	0.9600	C14—O4	1.209 (2)
C7—H7C	0.9600	C14—O5	1.319 (2)
C8—N1	1.465 (2)	C15—O5	1.435 (3)
C8—C9	1.550 (2)	C15—H15A	0.9600
C8—H8	0.9800	C15—H15B	0.9600
C9—C12	1.506 (2)	C15—H15C	0.9600
C9—C10	1.541 (2)	N1—O1	1.4707 (19)
C9—H9	0.9800

C2—C1—C6	118.35 (17)	O1—C10—C14	114.22 (15)
C2—C1—C8	122.56 (16)	O1—C10—C9	107.23 (13)
C6—C1—C8	119.07 (17)	C14—C10—C9	114.25 (13)
C1—C2—C3	120.1 (2)	O1—C10—H10	106.9
C1—C2—H2	119.9	C14—C10—H10	106.9
C3—C2—H2	119.9	C9—C10—H10	106.9
C4—C3—C2	121.9 (2)	N1—C11—H11A	109.5
C4—C3—H3	119.1	N1—C11—H11B	109.5
C2—C3—H3	119.1	H11A—C11—H11B	109.5
C3—C4—C5	117.47 (18)	N1—C11—H11C	109.5
C3—C4—C7	122.3 (3)	H11A—C11—H11C	109.5
C5—C4—C7	120.2 (3)	H11B—C11—H11C	109.5
C6—C5—C4	121.5 (2)	O2—C12—O3	123.68 (17)
C6—C5—H5	119.2	O2—C12—C9	125.72 (17)
C4—C5—H5	119.2	O3—C12—C9	110.57 (16)
C5—C6—C1	120.6 (2)	O3—C13—H13A	109.5
C5—C6—H6	119.7	O3—C13—H13B	109.5
C1—C6—H6	119.7	H13A—C13—H13B	109.5
C4—C7—H7A	109.5	O3—C13—H13C	109.5
C4—C7—H7B	109.5	H13A—C13—H13C	109.5
H7A—C7—H7B	109.5	H13B—C13—H13C	109.5
C4—C7—H7C	109.5	O4—C14—O5	124.86 (18)
H7A—C7—H7C	109.5	O4—C14—C10	120.68 (18)
H7B—C7—H7C	109.5	O5—C14—C10	114.39 (15)
N1—C8—C1	112.71 (14)	O5—C15—H15A	109.5
N1—C8—C9	101.23 (13)	O5—C15—H15B	109.5
C1—C8—C9	116.23 (14)	H15A—C15—H15B	109.5
N1—C8—H8	108.8	O5—C15—H15C	109.5
C1—C8—H8	108.8	H15A—C15—H15C	109.5
C9—C8—H8	108.8	H15B—C15—H15C	109.5
C12—C9—C10	113.98 (14)	C11—N1—C8	113.54 (15)
C12—C9—C8	110.07 (13)	C11—N1—O1	104.36 (14)
C10—C9—C8	100.72 (13)	C8—N1—O1	101.21 (13)
C12—C9—H9	110.6	C10—O1—N1	105.84 (11)
C10—C9—H9	110.6	C12—O3—C13	116.79 (18)
C8—C9—H9	110.6	C14—O5—C15	115.34 (17)

C6—C1—C2—C3	0.5 (3)	C8—C9—C10—C14	−137.37 (16)
C8—C1—C2—C3	178.76 (17)	C10—C9—C12—O2	−29.1 (3)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C12—O2	83.2 (2)
C2—C3—C4—C5	−0.2 (3)	C10—C9—C12—O3	152.90 (14)
C2—C3—C4—C7	178.4 (2)	C8—C9—C12—O3	−94.81 (17)
C3—C4—C5—C6	1.3 (3)	O1—C10—C14—O4	172.80 (15)
C7—C4—C5—C6	−177.4 (2)	C9—C10—C14—O4	−63.2 (2)
C4—C5—C6—C1	−1.4 (3)	O1—C10—C14—O5	−4.3 (2)
C2—C1—C6—C5	0.5 (3)	C9—C10—C14—O5	119.63 (16)
C8—C1—C6—C5	−177.80 (18)	C1—C8—N1—C11	75.72 (19)
C2—C1—C8—N1	31.2 (2)	C9—C8—N1—C11	−159.42 (16)
C6—C1—C8—N1	−150.60 (17)	C1—C8—N1—O1	−173.05 (13)
C2—C1—C8—C9	−85.0 (2)	C9—C8—N1—O1	−48.19 (14)
C6—C1—C8—C9	93.2 (2)	C14—C10—O1—N1	107.82 (15)
N1—C8—C9—C12	−85.19 (15)	C9—C10—O1—N1	−19.84 (17)
C1—C8—C9—C12	37.3 (2)	C11—N1—O1—C10	161.41 (16)
N1—C8—C9—C10	35.45 (15)	C8—N1—O1—C10	43.31 (16)
C1—C8—C9—C10	157.90 (15)	O2—C12—O3—C13	−6.6 (3)
C12—C9—C10—O1	108.09 (17)	C9—C12—O3—C13	171.52 (16)
C8—C9—C10—O1	−9.72 (16)	O4—C14—O5—C15	0.9 (3)
C12—C9—C10—C14	−19.6 (2)	C10—C14—O5—C15	177.92 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.60	3.300 (2)	133
C6—H6···O2ⁱⁱ	0.93	2.44	3.312 (3)	157
C9—H9···N1ⁱⁱ	0.98	2.55	3.497 (2)	162
C10—H10···O5ⁱⁱ	0.98	2.66	3.481 (2)	142
C15—H15a···O4ⁱⁱⁱ	0.96	2.64	3.403 (3)	137

Symmetry codes: (i) −x+1, y, z−1/2; (ii) −x+1, y, z+1/2; (iii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉NO₅
M_r	293.31
Crystal system, space group	Orthorhombic, Ccc2
Temperature (K)	296
a, b, c (Å)	15.3832 (7), 19.7959 (8), 9.9612 (3)
V (Å³)	3033.4 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.78 × 0.45 × 0.27

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.973, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11187, 1672, 1554
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.074, 1.07
No. of reflections	1672
No. of parameters	192
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.10

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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.60	3.300 (2)	133
C6—H6···O2ⁱⁱ	0.93	2.44	3.312 (3)	157
C9—H9···N1ⁱⁱ	0.98	2.55	3.497 (2)	162
C10—H10···O5ⁱⁱ	0.98	2.66	3.481 (2)	142
C15—H15a···O4ⁱⁱⁱ	0.96	2.64	3.403 (3)	137

Symmetry codes: (i) −x+1, y, z−1/2; (ii) −x+1, y, z+1/2; (iii) x, −y+1, z−1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant No. F.279 of the University Research Fund).

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