2-[(3R,6R)-6-Methyl-2,5-dioxomorph­olin-3-yl]-N-(propan-2-yl)acetamide

The molecular conformation of the title compound, C₁₀H₁₆N₂O₄, is determined by an intra­molecular N—H⋯O hydrogen bond involving the morpholine NH group and the amide O atom. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into chains along the a-axis direction.

Related literature

For the synthesis of polydepsipeptides, see: Feng et al. (2002); Hughes & Sleebs (2005); In't Veld et al. (1992,1994); Jörres et al. (1998). For the synthesis of title compound, see: Wang & Feng (1997).

Experimental

Crystal data

• C₁₀H₁₆N₂O₄

• M_r = 228.25

• Monoclinic, P 2₁

• a = 8.038 (3) Å

• b = 5.678 (2) Å

• c = 12.656 (5) Å

• β = 105.476 (4)°

• V = 556.6 (3) ų

• Z = 2

• Mo Kα radiation

• μ = 0.11 mm⁻¹

• T = 296 K

• 0.28 × 0.26 × 0.24 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.971, T_max = 0.975

• 3796 measured reflections

• 1111 independent reflections

• 973 reflections with I > 2σ(I)

• R_int = 0.026

Refinement

• R[F² > 2σ(F²)] = 0.036

• wR(F²) = 0.085

• S = 1.16

• 1111 reflections

• 153 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.13 e Å⁻³

• Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.85 (4)	2.09 (3)	2.763 (4)	136 (3)
N2—H2N⋯O1^i	0.82 (3)	2.11 (3)	2.926 (3)	170 (3)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

S1. Comment

Polydepsipeptides, copolymers of α-hydroxy acids and α-amino acids, are the most important representatives of biodegradable polyesteramides. Morpholine-2,5-dione derivatives are a series of monomers which were used to synthesize polydepsipeptides via ring-opening polymerization. (In't Veld et al., 1992,1994). In recent years, all kinds of functional groups are introduced into these monomers in order to synthesize functional polydepsipeptides (Feng et al., 2002; Jörres et al., 1998; Hughes & Sleebs, 2005). In our current research, related to this topic, we have designed and synthesized the title compound, which includes the isopropyl amide functional group (Fig. 1). In the crystal structure of the title compound, C₁₀H₁₆N₂O₄, there are two kinds of hydrogen bonds, one is intramolecular N—H···O [H···O = 2.09 (3) Å] hydrogen bond, the other is intermolecular N—H···O [H···O = 2.11 (3) Å] hydrogen bond which links molecules into the one-dimensional chains along the a-axis direction (Fig. 2).

Related literature

For the synthesis of polydepsipeptides, see: Feng et al. (2002); Hughes & Sleebs (2005); In't Veld et al. (1992,1994); Jörres et al. (1998). For the synthesis of title compound, see: Wang & Feng (1997).

S2. Experimental

All reagents used in the syntheses were of analytical grade and used without further purification. The title compound was prepared according to the literature method (Wang & Feng, 1997). Single crystals were grown from ethyl acetate solution by slow evaporation at room temperature.

S3. Refinement

All H atoms were placed in calculated positions, with C—H distances ranging from 0.96 to 0.98 Å, and N—H distances ranging from 0.82 to 0.85 Å. They were refined in the riding-model approximation, with U_iso(H) = 1.2U_eq(carrier C, N) or U_iso(H) = 1.5U_eq(C of methyl group).

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The hydrogen-bonded chain in the structure of title compound.

2-[(3R,6R)-6-methyl-2,5-dioxomorpholin-3-yl]- N-(propan-2-yl)acetamide

Crystal data

C10H16N2O4	F(000) = 244
Mr = 228.25	Dx = 1.362 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2019 reflections
a = 8.038 (3) Å	θ = 2.6–28.4°
b = 5.678 (2) Å	µ = 0.11 mm^−1
c = 12.656 (5) Å	T = 296 K
β = 105.476 (4)°	Block, colourless
V = 556.6 (3) Å^3	0.28 × 0.26 × 0.24 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	1111 independent reflections
Radiation source: fine-focus sealed tube	973 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ϕ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
Tmin = 0.971, Tmax = 0.975	k = −6→6
3796 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0381P)^2 + 0.0663P] where P = (Fo^2 + 2Fc^2)/3
1111 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.13 e Å^−3
1 restraint	Δρmin = −0.13 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3090 (3)	0.0143 (5)	0.7877 (2)	0.0396 (6)
H1N	0.303 (3)	−0.121 (7)	0.759 (2)	0.041 (9)*
O1	0.0310 (2)	0.0204 (5)	0.78753 (18)	0.0587 (6)
C2	0.1717 (3)	0.1165 (6)	0.8051 (2)	0.0395 (7)
N2	0.7140 (3)	−0.2115 (4)	0.66322 (19)	0.0384 (6)
H2N	0.803 (4)	−0.138 (6)	0.691 (2)	0.041 (9)*
O2	0.6493 (2)	0.3811 (4)	0.93137 (16)	0.0480 (6)
C3	0.1981 (3)	0.3664 (6)	0.8450 (2)	0.0425 (7)
H3A	0.1803	0.4699	0.7810	0.051*
O3	0.3725 (2)	0.4038 (4)	0.91393 (15)	0.0426 (5)
O4	0.4538 (2)	−0.3182 (4)	0.67977 (16)	0.0500 (6)
C5	0.5079 (3)	0.3148 (5)	0.8859 (2)	0.0343 (7)
C6	0.4708 (3)	0.1354 (5)	0.7952 (2)	0.0310 (6)
H6A	0.4607	0.2184	0.7259	0.037*
C7	0.0782 (4)	0.4419 (7)	0.9102 (3)	0.0641 (11)
H7A	0.1023	0.6023	0.9332	0.096*
H7B	0.0939	0.3426	0.9735	0.096*
H7C	−0.0388	0.4295	0.8659	0.096*
C8	0.6152 (3)	−0.0437 (5)	0.8098 (2)	0.0351 (7)
H8A	0.7244	0.0380	0.8203	0.042*
H8B	0.6210	−0.1370	0.8749	0.042*
C9	0.5878 (3)	−0.2038 (5)	0.7122 (2)	0.0355 (7)
C10	0.7090 (3)	−0.3549 (6)	0.5672 (2)	0.0409 (7)
H10A	0.5898	−0.3578	0.5211	0.049*
C11	0.8204 (5)	−0.2421 (7)	0.5025 (3)	0.0704 (11)
H11A	0.7822	−0.0836	0.4839	0.106*
H11B	0.8118	−0.3306	0.4366	0.106*
H11C	0.9384	−0.2403	0.5458	0.106*
C12	0.7629 (5)	−0.6010 (7)	0.5983 (3)	0.0634 (10)
H12A	0.6895	−0.6672	0.6392	0.095*
H12B	0.8803	−0.6023	0.6424	0.095*
H12C	0.7538	−0.6927	0.5332	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0359 (13)	0.0329 (15)	0.0509 (16)	−0.0098 (12)	0.0133 (11)	−0.0121 (14)
O1	0.0304 (11)	0.0629 (16)	0.0810 (15)	−0.0155 (11)	0.0121 (10)	−0.0133 (14)
C2	0.0326 (15)	0.0445 (19)	0.0402 (15)	−0.0056 (14)	0.0077 (12)	−0.0024 (14)
N2	0.0345 (13)	0.0397 (15)	0.0424 (14)	−0.0085 (12)	0.0127 (11)	−0.0152 (12)
O2	0.0342 (10)	0.0475 (13)	0.0588 (12)	−0.0081 (11)	0.0064 (9)	−0.0169 (11)
C3	0.0330 (14)	0.0476 (19)	0.0453 (17)	−0.0025 (15)	0.0073 (12)	−0.0029 (15)
O3	0.0322 (9)	0.0479 (13)	0.0481 (11)	−0.0059 (10)	0.0115 (8)	−0.0154 (10)
O4	0.0389 (11)	0.0542 (15)	0.0574 (13)	−0.0152 (11)	0.0138 (9)	−0.0229 (12)
C5	0.0346 (15)	0.0343 (18)	0.0359 (14)	−0.0045 (13)	0.0125 (11)	0.0009 (13)
C6	0.0299 (13)	0.0330 (16)	0.0305 (14)	−0.0062 (12)	0.0088 (10)	−0.0015 (13)
C7	0.0410 (17)	0.077 (3)	0.077 (2)	−0.0029 (19)	0.0215 (15)	−0.028 (2)
C8	0.0330 (14)	0.0361 (18)	0.0351 (14)	−0.0045 (13)	0.0072 (11)	−0.0050 (13)
C9	0.0340 (14)	0.0340 (17)	0.0375 (15)	−0.0004 (13)	0.0077 (11)	−0.0011 (14)
C10	0.0370 (15)	0.0457 (19)	0.0394 (16)	0.0007 (15)	0.0091 (12)	−0.0102 (15)
C11	0.112 (3)	0.051 (2)	0.063 (2)	−0.001 (2)	0.050 (2)	−0.003 (2)
C12	0.091 (3)	0.039 (2)	0.069 (2)	0.002 (2)	0.035 (2)	−0.0075 (19)

Geometric parameters (Å, º)

N1—C2	1.317 (4)	C6—H6A	0.9800
N1—C6	1.452 (3)	C7—H7A	0.9600
N1—H1N	0.85 (4)	C7—H7B	0.9600
O1—C2	1.222 (3)	C7—H7C	0.9600
C2—C3	1.502 (5)	C8—C9	1.502 (4)
N2—C9	1.323 (3)	C8—H8A	0.9700
N2—C10	1.454 (4)	C8—H8B	0.9700
N2—H2N	0.82 (3)	C10—C12	1.485 (5)
O2—C5	1.190 (3)	C10—C11	1.508 (4)
C3—O3	1.456 (3)	C10—H10A	0.9800
C3—C7	1.489 (4)	C11—H11A	0.9600
C3—H3A	0.9800	C11—H11B	0.9600
O3—C5	1.331 (3)	C11—H11C	0.9600
O4—C9	1.231 (3)	C12—H12A	0.9600
C5—C6	1.504 (4)	C12—H12B	0.9600
C6—C8	1.517 (4)	C12—H12C	0.9600
C2—N1—C6	123.8 (3)	H7A—C7—H7C	109.5
C2—N1—H1N	121.1 (19)	H7B—C7—H7C	109.5
C6—N1—H1N	114.0 (19)	C9—C8—C6	111.5 (2)
O1—C2—N1	123.3 (3)	C9—C8—H8A	109.3
O1—C2—C3	121.6 (3)	C6—C8—H8A	109.3
N1—C2—C3	115.0 (3)	C9—C8—H8B	109.3
C9—N2—C10	123.8 (3)	C6—C8—H8B	109.3
C9—N2—H2N	118 (2)	H8A—C8—H8B	108.0
C10—N2—H2N	118 (2)	O4—C9—N2	122.6 (3)
O3—C3—C7	106.7 (2)	O4—C9—C8	121.1 (2)
O3—C3—C2	111.5 (3)	N2—C9—C8	116.3 (2)
C7—C3—C2	113.8 (3)	N2—C10—C12	111.4 (3)
O3—C3—H3A	108.2	N2—C10—C11	109.1 (3)
C7—C3—H3A	108.2	C12—C10—C11	111.7 (3)
C2—C3—H3A	108.2	N2—C10—H10A	108.2
C5—O3—C3	120.7 (2)	C12—C10—H10A	108.2
O2—C5—O3	119.6 (3)	C11—C10—H10A	108.2
O2—C5—C6	123.5 (2)	C10—C11—H11A	109.5
O3—C5—C6	116.8 (2)	C10—C11—H11B	109.5
N1—C6—C5	111.3 (2)	H11A—C11—H11B	109.5
N1—C6—C8	109.5 (2)	C10—C11—H11C	109.5
C5—C6—C8	111.9 (2)	H11A—C11—H11C	109.5
N1—C6—H6A	108.0	H11B—C11—H11C	109.5
C5—C6—H6A	108.0	C10—C12—H12A	109.5
C8—C6—H6A	108.0	C10—C12—H12B	109.5
C3—C7—H7A	109.5	H12A—C12—H12B	109.5
C3—C7—H7B	109.5	C10—C12—H12C	109.5
H7A—C7—H7B	109.5	H12A—C12—H12C	109.5
C3—C7—H7C	109.5	H12B—C12—H12C	109.5
C6—N1—C2—O1	172.1 (3)	O2—C5—C6—N1	155.1 (3)
C6—N1—C2—C3	−5.8 (4)	O3—C5—C6—N1	−25.9 (3)
O1—C2—C3—O3	149.0 (3)	O2—C5—C6—C8	32.4 (4)
N1—C2—C3—O3	−33.1 (3)	O3—C5—C6—C8	−148.7 (2)
O1—C2—C3—C7	28.2 (4)	N1—C6—C8—C9	63.2 (3)
N1—C2—C3—C7	−153.9 (3)	C5—C6—C8—C9	−173.0 (2)
C7—C3—O3—C5	168.1 (3)	C10—N2—C9—O4	−0.3 (4)
C2—C3—O3—C5	43.3 (4)	C10—N2—C9—C8	−179.4 (3)
C3—O3—C5—O2	166.4 (3)	C6—C8—C9—O4	−55.6 (3)
C3—O3—C5—C6	−12.6 (4)	C6—C8—C9—N2	123.5 (3)
C2—N1—C6—C5	36.3 (4)	C9—N2—C10—C12	−83.3 (3)
C2—N1—C6—C8	160.4 (2)	C9—N2—C10—C11	152.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.85 (4)	2.09 (3)	2.763 (4)	136 (3)
N2—H2N···O1^i	0.82 (3)	2.11 (3)	2.926 (3)	170 (3)

Symmetry code: (i) x+1, y, z.