Methyl 2-[(4-chloro-2-meth-oxy-5-oxo-2,5-dihydro-furan-3-yl)amino]-acetate.

The title compound, C(8)H(10)ClNO(5), was obtained via a tandem Michael addition-elimination reaction of 3,4-dichloro-5-meth-oxy-furan-2(5H)-one and glycine methyl ester in the presence of triethyl-amine. The mol-ecular structure contains an approximately planar [maximum atomic deviation = 0.010 (2) Å] five-membered furan-one ring. The crystal packing is stabilized by inter-molecular N-H⋯O and weak C-H⋯O hydrogen bonding.

Related literature

For biologicallly active 4-amino-2(5H)-furan­ones, see: Kimura et al. (2000 ▶); Tanoury et al. (2008 ▶). For related furan­one structures, see: Song et al. (2009b ▶); Li et al. (2009 ▶). For the synthesis, see: Song et al. (2009a ▶).

Experimental

Crystal data

C8H10ClNO5

M = 235.62

Monoclinic,

a = 5.1366 (10) Å

b = 9.8316 (19) Å

c = 20.685 (4) Å

β = 102.532 (4)°

V = 1019.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.21 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

3333 measured reflections

1714 independent reflections

1221 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 1.05

1714 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002461X/xu2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002461X/xu2785Isup2.hkl

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

C8H10ClNO5	F(000) = 488
Mr = 235.62	Dx = 1.535 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 826 reflections
a = 5.1366 (10) Å	θ = 2.3–25.2°
b = 9.8316 (19) Å	µ = 0.38 mm−1
c = 20.685 (4) Å	T = 296 K
β = 102.532 (4)°	Cubic, colorless
V = 1019.7 (3) Å3	0.21 × 0.21 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	1221 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.2°, θmin = 2.0°
φ and ω scans	h = −5→6
3333 measured reflections	k = −5→11
1714 independent reflections	l = −24→24

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) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.3573P] where P = (Fo2 + 2Fc2)/3
1714 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3, TMS): 3.52 (3H, s, CH, CH3), 3.82 (3H, s, CH, CH3), 4.29 (2H, s, CH, CH2), 5.75 (1H, s, CH).

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
Cl1	0.60822 (13)	0.63332 (7)	0.79402 (3)	0.0553 (3)
O1	−0.0366 (3)	0.45788 (17)	0.69305 (7)	0.0483 (5)
O2	0.1905 (4)	0.39330 (18)	0.79393 (8)	0.0539 (5)
O3	−0.0115 (3)	0.51417 (18)	0.58504 (7)	0.0514 (5)
O4	0.1774 (4)	0.86029 (19)	0.48157 (8)	0.0584 (5)
O5	0.5179 (4)	0.7421 (2)	0.54029 (8)	0.0643 (6)
N1	0.3070 (4)	0.7560 (2)	0.65232 (9)	0.0422 (5)
H1	0.4557	0.7914	0.6723	0.051*
C1	0.1684 (5)	0.4711 (3)	0.74761 (11)	0.0430 (6)
C2	0.3270 (5)	0.5858 (2)	0.73770 (10)	0.0391 (6)
C3	0.2222 (4)	0.6466 (2)	0.67961 (10)	0.0370 (6)
C4	−0.0206 (5)	0.5655 (3)	0.64653 (11)	0.0431 (6)
H4	−0.1788	0.6234	0.6422	0.052*
C5	0.2212 (6)	0.4363 (3)	0.58209 (12)	0.0557 (7)
H5A	0.2345	0.3603	0.6118	0.084*
H5B	0.3767	0.4925	0.5948	0.084*
H5C	0.2083	0.4039	0.5377	0.084*
C6	0.1683 (5)	0.8198 (3)	0.59157 (11)	0.0437 (6)
H6A	0.1498	0.9162	0.5993	0.052*
H6B	−0.0092	0.7813	0.5785	0.052*
C7	0.3126 (5)	0.8008 (2)	0.53614 (11)	0.0406 (6)
C8	0.2996 (7)	0.8523 (3)	0.42456 (13)	0.0732 (9)
H8A	0.2823	0.7614	0.4072	0.110*
H8B	0.4851	0.8755	0.4378	0.110*
H8C	0.2122	0.9146	0.3911	0.110*

	U11	U22	U33	U12	U13	U23
Cl1	0.0510 (4)	0.0741 (5)	0.0358 (3)	−0.0075 (3)	−0.0018 (3)	−0.0010 (3)
O1	0.0403 (11)	0.0567 (11)	0.0465 (9)	−0.0055 (8)	0.0062 (7)	0.0025 (9)
O2	0.0549 (12)	0.0595 (12)	0.0498 (10)	0.0069 (9)	0.0166 (8)	0.0126 (9)
O3	0.0497 (12)	0.0609 (12)	0.0378 (9)	0.0078 (9)	−0.0033 (7)	−0.0068 (8)
O4	0.0615 (13)	0.0742 (13)	0.0422 (9)	0.0274 (10)	0.0172 (8)	0.0172 (9)
O5	0.0448 (12)	0.0992 (16)	0.0502 (10)	0.0270 (11)	0.0129 (8)	0.0102 (10)
N1	0.0366 (12)	0.0530 (13)	0.0352 (10)	−0.0009 (10)	0.0041 (8)	0.0014 (10)
C1	0.0370 (15)	0.0543 (16)	0.0393 (13)	0.0080 (12)	0.0119 (10)	−0.0011 (13)
C2	0.0365 (14)	0.0498 (15)	0.0305 (12)	0.0000 (11)	0.0061 (9)	−0.0013 (11)
C3	0.0323 (14)	0.0465 (14)	0.0332 (12)	0.0073 (11)	0.0094 (9)	−0.0029 (11)
C4	0.0369 (15)	0.0519 (16)	0.0389 (13)	0.0040 (11)	0.0045 (10)	0.0006 (12)
C5	0.0641 (19)	0.0567 (17)	0.0443 (14)	0.0112 (14)	0.0074 (12)	−0.0074 (13)
C6	0.0427 (16)	0.0466 (15)	0.0422 (13)	0.0086 (12)	0.0099 (11)	0.0054 (11)
C7	0.0382 (16)	0.0427 (14)	0.0400 (13)	0.0001 (12)	0.0067 (11)	−0.0007 (11)
C8	0.087 (2)	0.093 (2)	0.0451 (15)	0.0227 (19)	0.0262 (15)	0.0180 (16)

Cl1—C2	1.712 (2)	C2—C3	1.345 (3)
O1—C1	1.372 (3)	C3—C4	1.513 (3)
O1—C4	1.444 (3)	C4—H4	0.9800
O2—C1	1.212 (3)	C5—H5A	0.9600
O3—C4	1.378 (3)	C5—H5B	0.9600
O3—C5	1.432 (3)	C5—H5C	0.9600
O4—C7	1.326 (3)	C6—C7	1.506 (3)
O4—C8	1.453 (3)	C6—H6A	0.9700
O5—C7	1.189 (3)	C6—H6B	0.9700
N1—C3	1.331 (3)	C8—H8A	0.9600
N1—C6	1.446 (3)	C8—H8B	0.9600
N1—H1	0.8600	C8—H8C	0.9600
C1—C2	1.432 (4)
C1—O1—C4	109.53 (18)	O3—C5—H5A	109.5
C4—O3—C5	115.52 (18)	O3—C5—H5B	109.5
C7—O4—C8	115.4 (2)	H5A—C5—H5B	109.5
C3—N1—C6	125.0 (2)	O3—C5—H5C	109.5
C3—N1—H1	117.5	H5A—C5—H5C	109.5
C6—N1—H1	117.5	H5B—C5—H5C	109.5
O2—C1—O1	121.0 (2)	N1—C6—C7	112.1 (2)
O2—C1—C2	130.7 (2)	N1—C6—H6A	109.2
O1—C1—C2	108.4 (2)	C7—C6—H6A	109.2
C3—C2—C1	110.4 (2)	N1—C6—H6B	109.2
C3—C2—Cl1	127.0 (2)	C7—C6—H6B	109.2
C1—C2—Cl1	122.65 (18)	H6A—C6—H6B	107.9
N1—C3—C2	129.3 (2)	O5—C7—O4	124.6 (2)
N1—C3—C4	123.20 (19)	O5—C7—C6	125.5 (2)
C2—C3—C4	107.5 (2)	O4—C7—C6	109.9 (2)
O3—C4—O1	111.4 (2)	O4—C8—H8A	109.5
O3—C4—C3	114.9 (2)	O4—C8—H8B	109.5
O1—C4—C3	104.20 (17)	H8A—C8—H8B	109.5
O3—C4—H4	108.7	O4—C8—H8C	109.5
O1—C4—H4	108.7	H8A—C8—H8C	109.5
C3—C4—H4	108.7	H8B—C8—H8C	109.5
C4—O1—C1—O2	178.2 (2)	C5—O3—C4—C3	52.9 (3)
C4—O1—C1—C2	−1.2 (2)	C1—O1—C4—O3	124.6 (2)
O2—C1—C2—C3	−177.5 (2)	C1—O1—C4—C3	0.2 (2)
O1—C1—C2—C3	1.9 (3)	N1—C3—C4—O3	57.7 (3)
O2—C1—C2—Cl1	2.5 (4)	C2—C3—C4—O3	−121.2 (2)
O1—C1—C2—Cl1	−178.19 (16)	N1—C3—C4—O1	179.8 (2)
C6—N1—C3—C2	−175.1 (2)	C2—C3—C4—O1	1.0 (2)
C6—N1—C3—C4	6.3 (3)	C3—N1—C6—C7	−110.6 (3)
C1—C2—C3—N1	179.5 (2)	C8—O4—C7—O5	−1.1 (4)
Cl1—C2—C3—N1	−0.4 (4)	C8—O4—C7—C6	178.5 (2)
C1—C2—C3—C4	−1.7 (3)	N1—C6—C7—O5	−0.7 (4)
Cl1—C2—C3—C4	178.33 (18)	N1—C6—C7—O4	179.7 (2)
C5—O3—C4—O1	−65.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.06	2.911 (3)	171
C6—H6B···O5ii	0.97	2.42	3.366 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.06	2.911 (3)	171
C6—H6B⋯O5ii	0.97	2.42	3.366 (3)	166

Symmetry codes: (i) ; (ii) .