Dimethyl cis-2-methyl-3-p-tolyl-isoxazolidine-4,5-dicarboxyl-ate.

In the mol-ecule of the title compound, C(15)H(19)NO(5), the isoxazole ring adopts an envelope conformation. In the crystal structure, weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules, 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 = 293.31

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.074

S = 1.07

1672 reflections

192 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.10 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/S1600536809009350/hk2635sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H19NO5	F(000) = 1248
Mr = 293.31	Dx = 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

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

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(Fo2) + (0.0483P)2 + 0.1649P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1672 reflections	Δρmax = 0.11 e Å−3
192 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) ; (ii) ; (iii) .