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

The molecular conformation of the title compound, C(10)H(16)N(2)O(4), is determined by an intra-molecular N-H⋯O hydrogen bond involving the morpholine NH group and the amide O atom. In the crystal, mol-ecules 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 = 228.25

Monoclinic,

a = 8.038 (3) Å

b = 5.678 (2) Å

c = 12.656 (5) Å

β = 105.476 (4)°

V = 556.6 (3) Å3

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.16

1111 reflections

153 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007945/yk2036sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007945/yk2036Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007945/yk2036Isup3.cml

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

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) Å3	0.28 × 0.26 × 0.24 mm
Z = 2

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 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.0663P] where P = (Fo2 + 2Fc2)/3
1111 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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.

	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*

	U11	U22	U33	U12	U13	U23
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)

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)

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···O1i	0.82 (3)	2.11 (3)	2.926 (3)	170 (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⋯O1i	0.82 (3)	2.11 (3)	2.926 (3)	170 (3)

Symmetry code: (i) .