5-(Methoxy-carbon-yl)thio-phene-2-carboxylic acid.

In the title compound, C(7)H(6)O(4)S, a monoester derivative of 2,5-thio-phene-dicarboxylic acid, the carboxylic acid and the carboxylic acid ester groups are approximately coplanar with thio-phene ring, making a dihedral angle of 3.1 (4) and 3.6 (4)°, respectively. In the crystal structure, mol-ecules are connected by classical inter-molecular O-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For a related structure, see: Zhao et al. (2009 ▶).

Experimental

Crystal data

C7H6O4S

M = 186.19

Monoclinic,

a = 18.2813 (18) Å

b = 5.9833 (6) Å

c = 7.3446 (8) Å

β = 99.081 (1)°

V = 793.30 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.40 × 0.28 × 0.12 mm

Data collection

Siemens SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.864, T max = 0.956

3914 measured reflections

1398 independent reflections

958 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 0.96

1398 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809053161/rk2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053161/rk2181Isup2.hkl

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

C7H6O4S	F(000) = 384
Mr = 186.19	Dx = 1.559 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 978 reflections
a = 18.2813 (18) Å	θ = 2.3–25.7°
b = 5.9833 (6) Å	µ = 0.38 mm−1
c = 7.3446 (8) Å	T = 298 K
β = 99.081 (1)°	Block, colourless
V = 793.30 (14) Å3	0.40 × 0.28 × 0.12 mm
Z = 4

Siemens SMART APEX CCD area-detector diffractometer	1398 independent reflections
Radiation source: fine–focus sealed tube	958 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→21
Tmin = 0.864, Tmax = 0.956	k = −6→7
3914 measured reflections	l = −8→8

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
1398 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 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
O1	0.36617 (8)	0.4062 (3)	1.0635 (2)	0.0477 (5)
O2	0.40524 (9)	0.7617 (3)	1.0853 (3)	0.0579 (5)
O3	0.07899 (9)	0.3919 (3)	0.6150 (2)	0.0593 (6)
O4	0.04479 (9)	0.7517 (3)	0.5849 (3)	0.0609 (6)
H4	0.0068	0.6974	0.5278	0.091*
S1	0.22488 (3)	0.47279 (11)	0.83803 (9)	0.0437 (3)
C1	0.35915 (12)	0.6246 (4)	1.0321 (3)	0.0398 (6)
C2	0.28593 (12)	0.6776 (4)	0.9231 (3)	0.0381 (6)
C3	0.25867 (13)	0.8855 (4)	0.8830 (3)	0.0419 (6)
H3	0.2847	1.0162	0.9174	0.050*
C4	0.18615 (13)	0.8808 (4)	0.7830 (3)	0.0421 (7)
H4A	0.1586	1.0079	0.7455	0.050*
C5	0.16150 (12)	0.6693 (4)	0.7481 (3)	0.0400 (6)
C6	0.09006 (13)	0.5956 (4)	0.6426 (3)	0.0432 (6)
C7	0.43390 (14)	0.3361 (5)	1.1788 (4)	0.0597 (8)
H7A	0.4753	0.3679	1.1174	0.090*
H7B	0.4318	0.1784	1.2017	0.090*
H7C	0.4395	0.4154	1.2938	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0345 (9)	0.0390 (11)	0.0619 (11)	0.0014 (8)	−0.0158 (8)	0.0037 (9)
O2	0.0401 (11)	0.0461 (12)	0.0783 (13)	−0.0098 (9)	−0.0190 (9)	0.0037 (10)
O3	0.0426 (11)	0.0456 (12)	0.0809 (14)	−0.0054 (9)	−0.0171 (9)	−0.0026 (10)
O4	0.0361 (10)	0.0523 (13)	0.0839 (13)	0.0006 (9)	−0.0226 (9)	−0.0035 (10)
S1	0.0357 (4)	0.0333 (4)	0.0563 (4)	−0.0016 (3)	−0.0105 (3)	−0.0007 (3)
C1	0.0310 (13)	0.0406 (16)	0.0446 (14)	−0.0017 (12)	−0.0045 (11)	0.0013 (12)
C2	0.0326 (13)	0.0355 (14)	0.0433 (14)	−0.0035 (10)	−0.0029 (11)	−0.0009 (11)
C3	0.0380 (14)	0.0327 (15)	0.0511 (15)	−0.0046 (12)	−0.0048 (11)	−0.0020 (12)
C4	0.0380 (14)	0.0349 (15)	0.0500 (15)	0.0040 (12)	−0.0034 (12)	0.0000 (12)
C5	0.0312 (14)	0.0393 (15)	0.0455 (14)	0.0007 (11)	−0.0063 (11)	0.0000 (12)
C6	0.0314 (13)	0.0434 (16)	0.0503 (15)	−0.0001 (13)	−0.0074 (11)	−0.0016 (13)
C7	0.0444 (16)	0.057 (2)	0.0694 (18)	0.0104 (14)	−0.0173 (13)	0.0124 (15)

O1—C1	1.330 (3)	C2—C3	1.355 (3)
O1—C7	1.447 (3)	C3—C4	1.411 (3)
O2—C1	1.196 (3)	C3—H3	0.9300
O3—C6	1.247 (3)	C4—C5	1.354 (3)
O4—C6	1.275 (3)	C4—H4A	0.9300
O4—H4	0.8200	C5—C6	1.477 (3)
S1—C2	1.708 (2)	C7—H7A	0.9600
S1—C5	1.709 (2)	C7—H7B	0.9600
C1—C2	1.482 (3)	C7—H7C	0.9600
C1—O1—C7	115.88 (19)	C3—C4—H4A	124.0
C6—O4—H4	109.5	C4—C5—C6	128.2 (2)
C2—S1—C5	90.67 (12)	C4—C5—S1	112.63 (16)
O2—C1—O1	125.0 (2)	C6—C5—S1	119.13 (18)
O2—C1—C2	124.0 (2)	O3—C6—O4	125.6 (2)
O1—C1—C2	111.00 (19)	O3—C6—C5	119.0 (2)
C3—C2—C1	125.7 (2)	O4—C6—C5	115.4 (2)
C3—C2—S1	112.49 (17)	O1—C7—H7A	109.5
C1—C2—S1	121.8 (2)	O1—C7—H7B	109.5
C2—C3—C4	112.2 (2)	H7A—C7—H7B	109.5
C2—C3—H3	123.9	O1—C7—H7C	109.5
C4—C3—H3	123.9	H7A—C7—H7C	109.5
C5—C4—C3	112.0 (2)	H7B—C7—H7C	109.5
C5—C4—H4A	124.0
C7—O1—C1—O2	3.1 (4)	C2—C3—C4—C5	−1.0 (3)
C7—O1—C1—C2	−176.3 (2)	C3—C4—C5—C6	−177.8 (2)
O2—C1—C2—C3	−6.1 (4)	C3—C4—C5—S1	0.8 (3)
O1—C1—C2—C3	173.3 (2)	C2—S1—C5—C4	−0.3 (2)
O2—C1—C2—S1	175.6 (2)	C2—S1—C5—C6	178.4 (2)
O1—C1—C2—S1	−5.0 (3)	C4—C5—C6—O3	175.4 (3)
C5—S1—C2—C3	−0.3 (2)	S1—C5—C6—O3	−3.1 (3)
C5—S1—C2—C1	178.2 (2)	C4—C5—C6—O4	−3.6 (4)
C1—C2—C3—C4	−177.6 (2)	S1—C5—C6—O4	177.90 (19)
S1—C2—C3—C4	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.82	2.639 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.82	2.639 (2)	173

Symmetry code: (i) .