3-[(2-Formyl-thio-phen-3-yl)(hy-droxy)meth-yl]thio-phene-2-carbaldehyde.

In the title compound, C(11)H(8)O(3)S(2), the dihedral angle between the mean planes of the two thio-phene rings is 65.10 (10)°. Intra-molecular C-H⋯O inter-actions form S(6) and S(7) ring motifs. In the crystal, chains along the a axis are formed by C-H⋯O inter-actions. Adjacent chains are connected into a three-dimensional network by C-H⋯O and O-H⋯O inter-actions.

Related literature

For details and applications of thio­phene-based aldehydes, see: Basu & Das (2011 ▶); Guarín et al. (2007 ▶); Herbivo et al. (2009 ▶); Jain et al. (2010 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For optical applications of formyl thio­phene derivatives, see: Raposo & Kirsch (2003 ▶); Raposo et al. (2004 ▶). For related Schiff base compounds reported by our group, see: Su et al. (2007a ▶, ▶, 2009 ▶).

Experimental

Crystal data

C11H8O3S2

M = 252.29

Monoclinic,

a = 7.6227 (18) Å

b = 10.136 (2) Å

c = 14.272 (3) Å

β = 101.998 (4)°

V = 1078.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.26 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.886, T max = 0.906

6687 measured reflections

2122 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.03

2122 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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) global, I. DOI: 10.1107/S1600536811052500/mw2040sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052500/mw2040Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052500/mw2040Isup3.cml

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

C11H8O3S2	F(000) = 520
Mr = 252.29	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2097 reflections
a = 7.6227 (18) Å	θ = 2.5–26.1°
b = 10.136 (2) Å	µ = 0.48 mm−1
c = 14.272 (3) Å	T = 293 K
β = 101.998 (4)°	Block, yellow
V = 1078.7 (4) Å3	0.26 × 0.24 × 0.21 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2122 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 9.00 pixels mm-1	θmax = 26.1°, θmin = 2.5°
phi and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −10→12
Tmin = 0.886, Tmax = 0.906	l = −17→17
6687 measured reflections

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) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.3301P] where P = (Fo2 + 2Fc2)/3
2122 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.18693 (8)	0.05474 (6)	0.40611 (4)	0.0483 (2)
S2	0.35779 (8)	0.71529 (6)	0.45073 (4)	0.04438 (19)
O1	0.2719 (2)	0.41275 (16)	0.18884 (10)	0.0461 (4)
H1	0.2189	0.3605	0.1490	0.069*
O3	−0.0407 (2)	0.72325 (18)	0.41728 (12)	0.0549 (5)
C2	0.2269 (3)	0.2727 (2)	0.32022 (14)	0.0333 (5)
O2	−0.1559 (2)	0.3386 (2)	0.33753 (15)	0.0696 (6)
C1	0.1038 (3)	0.2063 (2)	0.36192 (15)	0.0364 (5)
C8	0.2905 (3)	0.5135 (2)	0.33862 (14)	0.0328 (5)
C11	0.0174 (3)	0.6327 (2)	0.37609 (15)	0.0434 (5)
H11	−0.0644	0.5759	0.3388	0.052*
C7	0.2056 (3)	0.6090 (2)	0.38216 (14)	0.0356 (5)
C5	−0.0793 (3)	0.2385 (3)	0.36692 (18)	0.0480 (6)
H5	−0.1425	0.1769	0.3951	0.058*
C9	0.4790 (3)	0.5276 (2)	0.36272 (15)	0.0391 (5)
H9	0.5582	0.4716	0.3407	0.047*
C4	0.3810 (3)	0.0795 (2)	0.36802 (17)	0.0487 (6)
H4	0.4740	0.0184	0.3759	0.058*
C6	0.1976 (3)	0.4072 (2)	0.27314 (14)	0.0344 (5)
H6	0.0688	0.4260	0.2560	0.041*
C10	0.5322 (3)	0.6320 (2)	0.42159 (16)	0.0435 (5)
H10	0.6517	0.6553	0.4436	0.052*
C3	0.3852 (3)	0.1982 (2)	0.32482 (16)	0.0424 (5)
H3	0.4825	0.2276	0.3006	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0545 (4)	0.0366 (4)	0.0535 (4)	0.0026 (3)	0.0109 (3)	0.0055 (3)
S2	0.0443 (3)	0.0373 (3)	0.0493 (4)	−0.0010 (2)	0.0045 (2)	−0.0050 (3)
O1	0.0513 (10)	0.0534 (10)	0.0367 (8)	−0.0124 (8)	0.0166 (7)	−0.0050 (7)
O3	0.0456 (10)	0.0604 (12)	0.0575 (10)	0.0198 (8)	0.0077 (8)	−0.0096 (9)
C2	0.0316 (11)	0.0347 (12)	0.0339 (11)	−0.0004 (8)	0.0072 (8)	−0.0061 (9)
O2	0.0489 (11)	0.0614 (13)	0.1079 (16)	0.0157 (9)	0.0376 (10)	0.0192 (11)
C1	0.0396 (11)	0.0329 (12)	0.0374 (11)	0.0024 (9)	0.0094 (9)	−0.0012 (9)
C8	0.0331 (11)	0.0305 (11)	0.0348 (10)	0.0013 (8)	0.0073 (8)	0.0064 (8)
C11	0.0395 (12)	0.0456 (14)	0.0435 (12)	0.0073 (10)	0.0050 (10)	−0.0002 (10)
C7	0.0346 (11)	0.0351 (12)	0.0355 (11)	0.0012 (9)	0.0040 (8)	0.0025 (9)
C5	0.0430 (13)	0.0479 (15)	0.0586 (15)	−0.0019 (11)	0.0229 (11)	0.0016 (12)
C9	0.0322 (11)	0.0417 (13)	0.0451 (12)	0.0005 (9)	0.0118 (9)	0.0047 (10)
C4	0.0418 (13)	0.0418 (14)	0.0599 (15)	0.0112 (10)	0.0047 (11)	−0.0057 (11)
C6	0.0306 (10)	0.0379 (12)	0.0358 (11)	−0.0001 (9)	0.0094 (8)	0.0012 (9)
C10	0.0326 (11)	0.0455 (14)	0.0513 (13)	−0.0065 (10)	0.0061 (9)	0.0060 (11)
C3	0.0327 (11)	0.0430 (13)	0.0519 (13)	0.0018 (10)	0.0098 (10)	−0.0056 (11)

S1—C4	1.698 (3)	C8—C9	1.414 (3)
S1—C1	1.730 (2)	C8—C6	1.503 (3)
S2—C10	1.698 (2)	C11—C7	1.439 (3)
S2—C7	1.730 (2)	C11—H11	0.9300
O1—C6	1.434 (2)	C5—H5	0.9300
O1—H1	0.8200	C9—C10	1.359 (3)
O3—C11	1.222 (3)	C9—H9	0.9300
C2—C1	1.386 (3)	C4—C3	1.355 (3)
C2—C3	1.414 (3)	C4—H4	0.9300
C2—C6	1.515 (3)	C6—H6	0.9800
O2—C5	1.201 (3)	C10—H10	0.9300
C1—C5	1.450 (3)	C3—H3	0.9300
C8—C7	1.383 (3)
C4—S1—C1	91.70 (11)	C1—C5—H5	117.4
C10—S2—C7	91.10 (11)	C10—C9—C8	112.8 (2)
C6—O1—H1	109.5	C10—C9—H9	123.6
C1—C2—C3	111.6 (2)	C8—C9—H9	123.6
C1—C2—C6	125.23 (18)	C3—C4—S1	112.42 (18)
C3—C2—C6	123.17 (19)	C3—C4—H4	123.8
C2—C1—C5	131.0 (2)	S1—C4—H4	123.8
C2—C1—S1	111.02 (16)	O1—C6—C8	106.03 (16)
C5—C1—S1	117.75 (17)	O1—C6—C2	111.10 (17)
C7—C8—C9	111.52 (19)	C8—C6—C2	111.21 (16)
C7—C8—C6	125.27 (18)	O1—C6—H6	109.5
C9—C8—C6	123.21 (19)	C8—C6—H6	109.5
O3—C11—C7	123.5 (2)	C2—C6—H6	109.5
O3—C11—H11	118.2	C9—C10—S2	112.97 (17)
C7—C11—H11	118.2	C9—C10—H10	123.5
C8—C7—C11	130.1 (2)	S2—C10—H10	123.5
C8—C7—S2	111.65 (15)	C4—C3—C2	113.3 (2)
C11—C7—S2	118.27 (17)	C4—C3—H3	123.4
O2—C5—C1	125.2 (2)	C2—C3—H3	123.4
O2—C5—H5	117.4
C3—C2—C1—C5	−174.3 (2)	C7—C8—C9—C10	−0.8 (3)
C6—C2—C1—C5	4.5 (4)	C6—C8—C9—C10	178.91 (18)
C3—C2—C1—S1	0.4 (2)	C1—S1—C4—C3	0.90 (19)
C6—C2—C1—S1	179.10 (16)	C7—C8—C6—O1	129.0 (2)
C4—S1—C1—C2	−0.71 (16)	C9—C8—C6—O1	−50.6 (2)
C4—S1—C1—C5	174.72 (19)	C7—C8—C6—C2	−110.1 (2)
C9—C8—C7—C11	178.7 (2)	C9—C8—C6—C2	70.2 (2)
C6—C8—C7—C11	−1.0 (4)	C1—C2—C6—O1	−141.08 (19)
C9—C8—C7—S2	0.6 (2)	C3—C2—C6—O1	37.5 (3)
C6—C8—C7—S2	−179.07 (15)	C1—C2—C6—C8	101.1 (2)
O3—C11—C7—C8	−178.5 (2)	C3—C2—C6—C8	−80.3 (2)
O3—C11—C7—S2	−0.5 (3)	C8—C9—C10—S2	0.6 (3)
C10—S2—C7—C8	−0.24 (17)	C7—S2—C10—C9	−0.21 (18)
C10—S2—C7—C11	−178.60 (18)	S1—C4—C3—C2	−0.9 (3)
C2—C1—C5—O2	−4.2 (4)	C1—C2—C3—C4	0.3 (3)
S1—C1—C5—O2	−178.5 (2)	C6—C2—C3—C4	−178.46 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.98	2.43	3.101 (3)	125
C11—H11···O2	0.93	2.50	3.261 (3)	139
C4—H4···O1i	0.93	2.55	3.377 (3)	149
C9—H9···O2ii	0.93	2.57	3.458 (3)	160
C10—H10···O3ii	0.93	2.55	3.397 (3)	152
O1—H1···O3iii	0.82	2.03	2.825 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.98	2.43	3.101 (3)	125
C11—H11⋯O2	0.93	2.50	3.261 (3)	139
C4—H4⋯O1i	0.93	2.55	3.377 (3)	149
C9—H9⋯O2ii	0.93	2.57	3.458 (3)	160
C10—H10⋯O3ii	0.93	2.55	3.397 (3)	152
O1—H1⋯O3iii	0.82	2.03	2.825 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) .