Diethyl 5-acetamido-3-methyl-thio-phene-2,4-dicarboxyl-ate.

The title compound, C(13)H(17)NO(5)S, is approximately planar (r.m.s. deviation for the non-H atoms = 0.055 Å). Its conformation is stabilized by N-H⋯O and C-H⋯O hydrogen bonds, which both generate S(6) rings. The crystal packing only features van der Waals contacts.

Related literature

For a related crystal structure and background, see: Mukhtar et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H17NO5S

M = 299.34

Monoclinic,

a = 15.933 (3) Å

b = 4.6028 (6) Å

c = 20.152 (3) Å

β = 106.005 (7)°

V = 1420.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.25 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.983

10222 measured reflections

2518 independent reflections

1311 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.172

S = 1.02

2518 reflections

186 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045629/hb5730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045629/hb5730Isup2.hkl

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

C13H17NO5S	F(000) = 632
Mr = 299.34	Dx = 1.400 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1311 reflections
a = 15.933 (3) Å	θ = 2.1–25.1°
b = 4.6028 (6) Å	µ = 0.25 mm−1
c = 20.152 (3) Å	T = 296 K
β = 106.005 (7)°	Needle, orange
V = 1420.6 (4) Å3	0.25 × 0.10 × 0.08 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2518 independent reflections
Radiation source: fine-focus sealed tube	1311 reflections with I > 2σ(I)
graphite	Rint = 0.094
Detector resolution: 8.20 pixels mm-1	θmax = 25.1°, θmin = 2.1°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.972, Tmax = 0.983	l = −20→24
10222 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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3244P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2518 reflections	Δρmax = 0.25 e Å−3
186 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.31949 (8)	0.0384 (2)	0.49921 (6)	0.0506 (5)
O1	0.2674 (2)	0.0997 (7)	0.35864 (17)	0.0745 (17)
O2	0.1065 (2)	0.7124 (7)	0.48056 (18)	0.0619 (12)
O3	0.1245 (2)	0.6438 (6)	0.59347 (17)	0.0568 (12)
O4	0.4142 (3)	−0.1121 (7)	0.6963 (2)	0.0805 (17)
O5	0.4407 (2)	−0.2748 (6)	0.59982 (16)	0.0583 (11)
N1	0.1981 (2)	0.3879 (7)	0.4170 (2)	0.0505 (16)
C1	0.2371 (3)	0.2886 (8)	0.4826 (3)	0.0431 (16)
C2	0.2152 (3)	0.3811 (9)	0.5411 (2)	0.0441 (17)
C3	0.2680 (3)	0.2433 (9)	0.6015 (2)	0.0448 (16)
C4	0.3277 (3)	0.0560 (9)	0.5869 (2)	0.0470 (17)
C5	0.2156 (3)	0.2958 (10)	0.3575 (3)	0.058 (2)
C6	0.1661 (3)	0.4472 (11)	0.2930 (3)	0.072 (2)
C7	0.1450 (3)	0.5918 (9)	0.5342 (3)	0.0504 (19)
C8	0.0519 (3)	0.8434 (10)	0.5883 (3)	0.0568 (19)
C9	0.0353 (4)	0.8550 (11)	0.6579 (3)	0.081 (2)
C10	0.2625 (3)	0.2958 (10)	0.6742 (2)	0.0622 (19)
C11	0.3963 (3)	−0.1159 (10)	0.6338 (3)	0.0559 (19)
C12	0.5140 (3)	−0.4391 (10)	0.6418 (3)	0.067 (2)
C13	0.5539 (3)	−0.6035 (10)	0.5932 (3)	0.0692 (19)
H1	0.15902	0.52060	0.41285	0.0604*
H6A	0.18642	0.38122	0.25496	0.1074*
H6B	0.17496	0.65304	0.29852	0.1074*
H6C	0.10496	0.40458	0.28401	0.1074*
H8A	0.00031	0.77509	0.55396	0.0687*
H8B	0.06655	1.03516	0.57495	0.0687*
H9A	0.08548	0.93427	0.69089	0.1219*
H9B	0.02430	0.66237	0.67177	0.1219*
H9C	−0.01457	0.97565	0.65561	0.1219*
H10A	0.27447	0.49656	0.68603	0.0934*
H10B	0.30462	0.17622	0.70576	0.0934*
H10C	0.20497	0.24802	0.67713	0.0934*
H12A	0.49428	−0.57346	0.67146	0.0802*
H12B	0.55670	−0.30905	0.67064	0.0802*
H13A	0.57324	−0.46835	0.56419	0.1038*
H13B	0.51108	−0.73156	0.56500	0.1038*
H13C	0.60277	−0.71498	0.61936	0.1038*

	U11	U22	U33	U12	U13	U23
S1	0.0497 (8)	0.0563 (7)	0.0508 (9)	0.0004 (6)	0.0222 (6)	−0.0001 (6)
O1	0.081 (3)	0.088 (3)	0.057 (3)	0.026 (2)	0.023 (2)	−0.0013 (19)
O2	0.063 (2)	0.076 (2)	0.052 (2)	0.0152 (18)	0.025 (2)	0.0064 (18)
O3	0.056 (2)	0.068 (2)	0.054 (2)	0.0086 (16)	0.0279 (18)	0.0036 (16)
O4	0.095 (3)	0.094 (3)	0.050 (3)	0.029 (2)	0.016 (2)	0.005 (2)
O5	0.055 (2)	0.0638 (19)	0.057 (2)	0.0108 (16)	0.0172 (18)	0.0064 (16)
N1	0.054 (3)	0.059 (2)	0.044 (3)	0.0083 (18)	0.023 (2)	0.003 (2)
C1	0.041 (3)	0.047 (2)	0.046 (3)	−0.005 (2)	0.020 (2)	0.002 (2)
C2	0.042 (3)	0.049 (3)	0.045 (3)	−0.004 (2)	0.018 (2)	−0.005 (2)
C3	0.041 (3)	0.050 (2)	0.047 (3)	−0.009 (2)	0.018 (3)	0.000 (2)
C4	0.046 (3)	0.054 (3)	0.046 (3)	−0.006 (2)	0.021 (2)	0.002 (2)
C5	0.061 (4)	0.067 (3)	0.052 (4)	−0.007 (3)	0.025 (3)	−0.001 (3)
C6	0.078 (4)	0.094 (4)	0.050 (4)	0.005 (3)	0.029 (3)	0.005 (3)
C7	0.051 (3)	0.051 (3)	0.056 (4)	−0.012 (2)	0.026 (3)	−0.004 (3)
C8	0.046 (3)	0.065 (3)	0.063 (4)	0.009 (2)	0.021 (3)	−0.002 (3)
C9	0.075 (4)	0.114 (4)	0.070 (4)	0.016 (3)	0.046 (3)	0.001 (3)
C10	0.065 (4)	0.078 (3)	0.047 (3)	0.005 (3)	0.021 (3)	0.000 (3)
C11	0.053 (3)	0.057 (3)	0.058 (4)	−0.002 (2)	0.016 (3)	0.000 (3)
C12	0.058 (4)	0.070 (3)	0.068 (4)	0.010 (3)	0.010 (3)	0.010 (3)
C13	0.054 (3)	0.076 (3)	0.083 (4)	0.016 (3)	0.028 (3)	0.008 (3)

S1—C1	1.709 (5)	C8—C9	1.498 (8)
S1—C4	1.738 (4)	C12—C13	1.510 (7)
O1—C5	1.219 (6)	C6—H6A	0.9600
O2—C7	1.220 (6)	C6—H6B	0.9600
O3—C7	1.344 (6)	C6—H6C	0.9600
O3—C8	1.458 (6)	C8—H8A	0.9700
O4—C11	1.212 (7)	C8—H8B	0.9700
O5—C11	1.331 (6)	C9—H9A	0.9600
O5—C12	1.452 (6)	C9—H9B	0.9600
N1—C1	1.375 (7)	C9—H9C	0.9600
N1—C5	1.371 (7)	C10—H10A	0.9600
N1—H1	0.8600	C10—H10B	0.9600
C1—C2	1.386 (7)	C10—H10C	0.9600
C2—C3	1.424 (6)	C12—H12A	0.9700
C2—C7	1.458 (7)	C12—H12B	0.9700
C3—C10	1.511 (6)	C13—H13A	0.9600
C3—C4	1.374 (6)	C13—H13B	0.9600
C4—C11	1.464 (7)	C13—H13C	0.9600
C5—C6	1.494 (8)
C1—S1—C4	90.4 (3)	H6A—C6—H6B	109.00
C7—O3—C8	115.5 (4)	H6A—C6—H6C	109.00
C11—O5—C12	116.3 (4)	H6B—C6—H6C	109.00
C1—N1—C5	126.3 (4)	O3—C8—H8A	110.00
C1—N1—H1	117.00	O3—C8—H8B	110.00
C5—N1—H1	117.00	C9—C8—H8A	110.00
S1—C1—N1	122.1 (4)	C9—C8—H8B	110.00
N1—C1—C2	124.3 (4)	H8A—C8—H8B	109.00
S1—C1—C2	113.6 (4)	C8—C9—H9A	109.00
C1—C2—C7	119.3 (4)	C8—C9—H9B	109.00
C1—C2—C3	111.3 (4)	C8—C9—H9C	109.00
C3—C2—C7	129.4 (4)	H9A—C9—H9B	109.00
C2—C3—C10	125.4 (4)	H9A—C9—H9C	109.00
C2—C3—C4	112.2 (4)	H9B—C9—H9C	109.00
C4—C3—C10	122.4 (4)	C3—C10—H10A	110.00
C3—C4—C11	129.7 (4)	C3—C10—H10B	109.00
S1—C4—C11	117.7 (4)	C3—C10—H10C	110.00
S1—C4—C3	112.6 (3)	H10A—C10—H10B	109.00
O1—C5—N1	120.8 (5)	H10A—C10—H10C	109.00
O1—C5—C6	123.7 (5)	H10B—C10—H10C	109.00
N1—C5—C6	115.5 (4)	O5—C12—H12A	110.00
O2—C7—O3	121.4 (4)	O5—C12—H12B	110.00
O3—C7—C2	113.7 (4)	C13—C12—H12A	110.00
O2—C7—C2	124.9 (5)	C13—C12—H12B	110.00
O3—C8—C9	107.3 (4)	H12A—C12—H12B	108.00
O4—C11—O5	122.4 (5)	C12—C13—H13A	109.00
O4—C11—C4	125.6 (5)	C12—C13—H13B	110.00
O5—C11—C4	111.9 (4)	C12—C13—H13C	110.00
O5—C12—C13	107.3 (4)	H13A—C13—H13B	109.00
C5—C6—H6A	110.00	H13A—C13—H13C	109.00
C5—C6—H6B	110.00	H13B—C13—H13C	109.00
C5—C6—H6C	109.00
C4—S1—C1—N1	178.4 (4)	N1—C1—C2—C7	1.7 (7)
C4—S1—C1—C2	−0.8 (4)	C1—C2—C3—C4	0.6 (6)
C1—S1—C4—C3	1.1 (4)	C1—C2—C3—C10	179.3 (4)
C1—S1—C4—C11	−177.0 (4)	C7—C2—C3—C4	179.9 (5)
C8—O3—C7—O2	2.2 (6)	C7—C2—C3—C10	−1.4 (8)
C8—O3—C7—C2	−177.3 (4)	C1—C2—C7—O2	−5.3 (7)
C7—O3—C8—C9	175.9 (4)	C1—C2—C7—O3	174.1 (4)
C12—O5—C11—O4	−1.7 (7)	C3—C2—C7—O2	175.3 (5)
C12—O5—C11—C4	176.1 (4)	C3—C2—C7—O3	−5.2 (7)
C11—O5—C12—C13	179.5 (4)	C2—C3—C4—S1	−1.1 (5)
C5—N1—C1—S1	3.2 (6)	C2—C3—C4—C11	176.7 (5)
C5—N1—C1—C2	−177.7 (4)	C10—C3—C4—S1	−179.9 (3)
C1—N1—C5—O1	3.2 (7)	C10—C3—C4—C11	−2.1 (8)
C1—N1—C5—C6	−177.9 (4)	S1—C4—C11—O4	174.8 (4)
S1—C1—C2—C3	0.3 (5)	S1—C4—C11—O5	−2.9 (5)
S1—C1—C2—C7	−179.2 (3)	C3—C4—C11—O4	−2.9 (8)
N1—C1—C2—C3	−178.9 (4)	C3—C4—C11—O5	179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.99	2.652 (5)	133
C10—H10B···O4	0.96	2.24	2.995 (6)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.99	2.652 (5)	133
C10—H10B⋯O4	0.96	2.24	2.995 (6)	135