4,5-Dihydro­cyclo­penta­[b]thio­phen-6-one

Hanton, L.R.; Moratti, S.C.; Shi, Z.; Simpson, J.

doi:10.1107/S1600536811056042

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o371-o372

doi:10.1107/S1600536811056042

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4,5-Dihydrocyclopenta[b]thiophen-6-one

Lyall R. Hanton,^a Stephen C. Moratti,^a Zheng Shi ^a and Jim Simpson ^a ^*

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: jsimpson@alkali.otago.ac.nz

(Received 23 December 2011; accepted 28 December 2011; online 14 January 2012)

The title compound, C₇H₆OS, crystallizes with two similar molecules, 1 and 2, in the asymmetric unit. Both molecules are essentially planar with r.m.s. deviations of 0.0193 and 0.0107 Å for the planes through the nine non-H atoms of molecules 1 and 2, respectively. The thiophene and 4,5-dihydrocyclopentadienone rings are inclined at 2.40 (13)° in 1 and 0.64 (13)° in 2. In the crystal structure π–π [3.6542 (17) Å] and C—H⋯π contacts stack the molecules into columns in an inverse fashion along the b axis. An extensive series of C—H⋯O hydrogen bonds links the columns, generating an extended network structure.

Related literature

For low band-gap and fluorescent applications of conjugated thiophene vinylene oligomers, see: Blanchard et al. (1997 , 1998a ,b , 2006 ). For control of the band-gap in the corresponding polymers, see: Roncali et al. (1994 ). For standard bond lengths, see: Allen et al. (1987 ). For related structures, see: Chang et al. (2004 ); Bonini et al. (2004 ). For the synthetic route to the starting material, methyl 6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate, see: Cai et al. (2002 ); More & Finney (2002 ); Yang (2009 ).

Experimental

Crystal data

C₇H₆OS
M_r = 138.18
Triclinic, $[P \overline 1]$
a = 6.6133 (9) Å
b = 7.4894 (11) Å
c = 13.3213 (16) Å
α = 83.247 (8)°
β = 86.097 (7)°
γ = 71.363 (8)°
V = 620.54 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 92 K
0.55 × 0.28 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2011 ) T_min = 0.617, T_max = 0.745
5251 measured reflections
1522 independent reflections
1264 reflections with I > 2σ(I)
R_int = 0.040
θ_max = 22.1°

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.119
S = 1.11
1522 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the S1,C12,C13,C17,C18 and S2,C22,C23,C27,C28 thiophene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1ⁱ	0.99	2.52	3.473 (4)	160
C15—H15B⋯O1ⁱⁱ	0.99	2.59	3.489 (3)	151
C12—H12⋯O2ⁱⁱⁱ	0.95	2.43	3.370 (4)	168
C13—H13⋯O2^iv	0.95	2.65	3.275 (4)	124
C23—H23⋯O1^v	0.95	2.62	3.425 (4)	143
C24—H24A⋯O2^vi	0.99	2.52	3.480 (4)	164
C25—H25A⋯O2^vii	0.99	2.71	3.704 (3)	180
C25—H25B⋯Cg1^viii	0.99	2.79	3.561 (3)	135
C15—H15A⋯Cg4ⁱⁱⁱ	0.99	2.84	3.571 (3)	131
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) x, y+1, z; (iv) -x+2, -y, -z+1; (v) -x, -y+1, -z+1; (vi) x-1, y, z; (vii) -x+1, -y, -z+1; (viii) x, y-1, z.

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011) and SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and TITAN2000 (Hunter & Simpson, 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811056042/tk5042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811056042/tk5042Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811056042/tk5042Isup3.cml

checkCIF report

Comment top

The title compound is a key intermediate in the synthesis of many conjugated thiophene vinylene oligomers for low band-gap and fluorescent applications (Blanchard et al., 1997, 1998a,b, 2006). This is because the ethylene bridge in the resulting vinylene system flattens the ring and increases the conjugation between the neighbouring thiophene groups. This technique can also be used to control the band-gap in the corresponding polymers (Roncali et al., 1994)

The asymmetric unit of the triclinic unit cell of the title compound, I, contains two unique molecules, 1 and 2, Fig 1. These are closely similar and overlay (Macrae et al., 2008) with an r.m.s. deviation of only 0.024 Å. The molecules are approximately planar with r.m.s. deviations of 0.0193 and 0.0107 Å from the best fit planes through the nine non-hydrogen atoms in each of the two molecules, respectively. This is further illustrated by the fact that the thiophene and cyclopentadienone ring planes are inclined at 2.40 (13)° in molecule 1 and 0.64 (13)° in molecule 2. Bond distances in the molecule are normal (Allen et al., 1987) and similar to those observed in related molecules (Chang et al., 2004; Bonini et al., 2004).

In the crystal structure, molecules 1 and 2 are linked by C15–H15A···π and C25–H25B···π contacts into dimers. π–π Contacts of 3.6542 (17) Å, between the centroids of the thiophene rings of molecules 1 and 2, link these dimers, forming columns along the b axis, Fig. 2. An extensive series of C–H···O hydrogen bonds involving the carbonyl O atoms from both molecules join the columns into an extended network, Fig 3. Interestingly the S atoms are not involved in any close intermolecular interactions.

Related literature top

For low band-gap and fluorescent applications of conjugated thiophene vinylene oligomers, see: Blanchard et al. (1997, 1998a,b, 2006). For control of the band-gap in the corresponding polymers, see: Roncali et al. (1994). For standard bond lengths, see: Allen et al. (1987). For related structures, see: Chang et al. (2004); Bonini et al. (2004). For the synthetic route to the starting material, methyl 6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate, see: Cai et al. (2002); More & Finney (2002); Yang (2009).

Experimental top

Methyl 6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate was prepared by literature methods (Cai et al. 2002; More & Finney, 2002; Yang, 2009). Methyl 6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate (124 mg, 0.63 mmol) was dissolved in KOH (0.5 M) solution (H₂O/EtOH, v/v=1) and refluxed for 4 h. The solution was cooled to room temperature, extracted with EtOAc (3× 20 ml), then the combined organic layers were washed with water (2× 50 ml) and dried over MgSO₄. The solvent was evaporated in vacuo to yield transparent gold crystals (52.3 mg, 0.38 mmol) 60% yield. ¹H NMR (δ p.p.m., CDCl₃, 300 Hz): 7.890 (1H, d, J=3.6 Hz, C₄H₂S), 7.045 (1H, d, J=3.6 Hz, C₄H₂S), 3.049–2.974 (4H, m, CH₂CH₂).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011) and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of I with ellipsoids drawn at the 50% probability level.
	Fig. 2. π–π and C–H···π contacts forming columns along b, with contacts shown as dashed lines.
	Fig. 3. A general view of the crystal packing for the title compound with hydrogen bonds drawn as dashed lines.

4,5-Dihydrocyclopenta[b]thiophen-6-one top

Crystal data top

C₇H₆OS	Z = 4
M_r = 138.18	F(000) = 288
Triclinic, P1	D_x = 1.479 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6133 (9) Å	Cell parameters from 1413 reflections
b = 7.4894 (11) Å	θ = 3.1–22.0°
c = 13.3213 (16) Å	µ = 0.42 mm⁻¹
α = 83.247 (8)°	T = 92 K
β = 86.097 (7)°	Rectangular plate, yellow
γ = 71.363 (8)°	0.55 × 0.28 × 0.02 mm
V = 620.54 (14) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	1522 independent reflections
Radiation source: fine-focus sealed tube	1264 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 22.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −6→6
T_min = 0.617, T_max = 0.745	k = −7→7
5251 measured reflections	l = −14→14

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0713P)² + 0.0126P] where P = (F_o² + 2F_c²)/3
1522 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₇H₆OS	γ = 71.363 (8)°
M_r = 138.18	V = 620.54 (14) Å³
Triclinic, P1	Z = 4
a = 6.6133 (9) Å	Mo Kα radiation
b = 7.4894 (11) Å	µ = 0.42 mm⁻¹
c = 13.3213 (16) Å	T = 92 K
α = 83.247 (8)°	0.55 × 0.28 × 0.02 mm
β = 86.097 (7)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1522 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2011)	1264 reflections with I > 2σ(I)
T_min = 0.617, T_max = 0.745	R_int = 0.040
5251 measured reflections	θ_max = 22.1°

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.11	Δρ_max = 0.30 e Å⁻³
1522 reflections	Δρ_min = −0.34 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.46716 (12)	0.59750 (11)	0.65016 (6)	0.0210 (3)
C12	0.6994 (5)	0.5881 (4)	0.5819 (2)	0.0205 (8)
H12	0.7031	0.6465	0.5148	0.025*
C13	0.8795 (5)	0.4873 (4)	0.6343 (2)	0.0196 (8)
H13	1.0213	0.4668	0.6078	0.024*
C14	0.9491 (5)	0.3065 (4)	0.8221 (2)	0.0193 (8)
H14A	1.0453	0.3705	0.8447	0.023*
H14B	1.0345	0.1774	0.8064	0.023*
C15	0.7725 (5)	0.2999 (4)	0.9031 (2)	0.0196 (8)
H15A	0.7831	0.1670	0.9267	0.023*
H15B	0.7872	0.3637	0.9619	0.023*
C16	0.5581 (5)	0.4015 (4)	0.8544 (2)	0.0195 (8)
O1	0.3814 (3)	0.4238 (3)	0.89458 (15)	0.0248 (6)
C17	0.6113 (5)	0.4662 (4)	0.7517 (2)	0.0176 (8)
C18	0.8269 (5)	0.4181 (4)	0.7325 (2)	0.0165 (7)
S2	0.47328 (13)	0.09696 (11)	0.12918 (6)	0.0222 (3)
C22	0.2153 (5)	0.2131 (4)	0.0920 (2)	0.0228 (8)
H22	0.1814	0.2782	0.0266	0.027*
C23	0.0655 (5)	0.2020 (4)	0.1654 (2)	0.0223 (8)
H23	−0.0840	0.2574	0.1574	0.027*
C24	0.0802 (5)	0.0432 (4)	0.3591 (2)	0.0198 (8)
H24A	−0.0149	−0.0345	0.3558	0.024*
H24B	0.0024	0.1568	0.3937	0.024*
C25	0.2881 (5)	−0.0727 (4)	0.4135 (2)	0.0185 (8)
H25A	0.3004	−0.0146	0.4749	0.022*
H25B	0.2877	−0.2040	0.4339	0.022*
C26	0.4739 (5)	−0.0725 (4)	0.3396 (2)	0.0170 (8)
O2	0.6635 (3)	−0.1458 (3)	0.35756 (15)	0.0232 (6)
C27	0.3776 (5)	0.0332 (4)	0.2462 (2)	0.0181 (8)
C28	0.1598 (5)	0.0976 (4)	0.2551 (2)	0.0181 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0114 (5)	0.0241 (6)	0.0242 (5)	−0.0009 (4)	−0.0045 (4)	−0.0007 (4)
C12	0.0189 (19)	0.0248 (19)	0.0193 (17)	−0.0099 (15)	−0.0005 (14)	0.0000 (14)
C13	0.0099 (18)	0.0216 (18)	0.0250 (19)	−0.0011 (14)	0.0014 (14)	−0.0048 (14)
C14	0.0125 (18)	0.0215 (19)	0.0229 (18)	−0.0037 (14)	−0.0018 (14)	−0.0020 (14)
C15	0.0166 (19)	0.0200 (18)	0.0207 (17)	−0.0040 (14)	−0.0017 (14)	−0.0011 (14)
C16	0.016 (2)	0.0171 (19)	0.0265 (18)	−0.0050 (15)	−0.0030 (16)	−0.0075 (14)
O1	0.0106 (14)	0.0311 (14)	0.0318 (13)	−0.0052 (10)	0.0044 (11)	−0.0061 (10)
C17	0.0100 (18)	0.0170 (18)	0.0236 (17)	−0.0007 (14)	−0.0049 (13)	−0.0014 (14)
C18	0.0117 (18)	0.0167 (17)	0.0217 (18)	−0.0041 (13)	0.0000 (13)	−0.0049 (14)
S2	0.0177 (6)	0.0271 (6)	0.0217 (5)	−0.0079 (4)	0.0016 (4)	−0.0014 (4)
C22	0.023 (2)	0.0224 (19)	0.0212 (18)	−0.0055 (15)	−0.0037 (15)	0.0044 (14)
C23	0.0154 (19)	0.0226 (19)	0.0283 (19)	−0.0038 (15)	−0.0057 (16)	−0.0032 (15)
C24	0.0124 (18)	0.0219 (18)	0.0239 (18)	−0.0038 (14)	−0.0001 (14)	−0.0025 (14)
C25	0.0167 (19)	0.0197 (18)	0.0176 (17)	−0.0037 (14)	−0.0044 (14)	0.0013 (14)
C26	0.015 (2)	0.0152 (17)	0.0217 (18)	−0.0043 (14)	−0.0002 (14)	−0.0057 (13)
O2	0.0094 (14)	0.0281 (14)	0.0284 (13)	−0.0010 (10)	−0.0032 (10)	−0.0003 (10)
C27	0.0125 (19)	0.0203 (19)	0.0222 (17)	−0.0049 (14)	0.0008 (14)	−0.0064 (14)
C28	0.0138 (18)	0.0189 (18)	0.0221 (18)	−0.0047 (14)	−0.0013 (14)	−0.0052 (14)

Geometric parameters (Å, º) top

S1—C12	1.716 (3)	S2—C27	1.716 (3)
S1—C17	1.723 (3)	S2—C22	1.726 (3)
C12—C13	1.375 (4)	C22—C23	1.359 (4)
C12—H12	0.9500	C22—H22	0.9500
C13—C18	1.412 (4)	C23—C28	1.413 (4)
C13—H13	0.9500	C23—H23	0.9500
C14—C18	1.497 (4)	C24—C28	1.506 (4)
C14—C15	1.543 (4)	C24—C25	1.547 (4)
C14—H14A	0.9900	C24—H24A	0.9900
C14—H14B	0.9900	C24—H24B	0.9900
C15—C16	1.526 (4)	C25—C26	1.522 (4)
C15—H15A	0.9900	C25—H25A	0.9900
C15—H15B	0.9900	C25—H25B	0.9900
C16—O1	1.221 (4)	C26—O2	1.225 (4)
C16—C17	1.456 (4)	C26—C27	1.461 (4)
C17—C18	1.368 (4)	C27—C28	1.366 (4)

C12—S1—C17	90.47 (15)	C27—S2—C22	89.93 (15)
C13—C12—S1	113.1 (2)	C23—C22—S2	113.3 (2)
C13—C12—H12	123.5	C23—C22—H22	123.3
S1—C12—H12	123.5	S2—C22—H22	123.3
C12—C13—C18	111.3 (3)	C22—C23—C28	111.6 (3)
C12—C13—H13	124.3	C22—C23—H23	124.2
C18—C13—H13	124.3	C28—C23—H23	124.2
C18—C14—C15	103.4 (2)	C28—C24—C25	103.1 (2)
C18—C14—H14A	111.1	C28—C24—H24A	111.1
C15—C14—H14A	111.1	C25—C24—H24A	111.1
C18—C14—H14B	111.1	C28—C24—H24B	111.1
C15—C14—H14B	111.1	C25—C24—H24B	111.1
H14A—C14—H14B	109.0	H24A—C24—H24B	109.1
C16—C15—C14	107.4 (2)	C26—C25—C24	107.4 (2)
C16—C15—H15A	110.2	C26—C25—H25A	110.2
C14—C15—H15A	110.2	C24—C25—H25A	110.2
C16—C15—H15B	110.2	C26—C25—H25B	110.2
C14—C15—H15B	110.2	C24—C25—H25B	110.2
H15A—C15—H15B	108.5	H25A—C25—H25B	108.5
O1—C16—C17	128.2 (3)	O2—C26—C27	128.6 (3)
O1—C16—C15	126.6 (3)	O2—C26—C25	125.8 (3)
C17—C16—C15	105.1 (3)	C27—C26—C25	105.6 (3)
C18—C17—C16	112.5 (3)	C28—C27—C26	112.0 (3)
C18—C17—S1	112.4 (2)	C28—C27—S2	112.9 (2)
C16—C17—S1	135.1 (2)	C26—C27—S2	135.1 (2)
C17—C18—C13	112.7 (3)	C27—C28—C23	112.3 (3)
C17—C18—C14	111.5 (3)	C27—C28—C24	111.8 (3)
C13—C18—C14	135.8 (3)	C23—C28—C24	135.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the S1,C12,C13,C17,C18 and S2,C22,C23,C27,C28 thiophene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.99	2.52	3.473 (4)	160
C15—H15B···O1ⁱⁱ	0.99	2.59	3.489 (3)	151
C12—H12···O2ⁱⁱⁱ	0.95	2.43	3.370 (4)	168
C13—H13···O2^iv	0.95	2.65	3.275 (4)	124
C23—H23···O1^v	0.95	2.62	3.425 (4)	143
C24—H24A···O2^vi	0.99	2.52	3.480 (4)	164
C25—H25A···O2^vii	0.99	2.71	3.704 (3)	180
C25—H25B···Cg1^viii	0.99	2.79	3.561 (3)	135
C15—H15A···Cg4ⁱⁱⁱ	0.99	2.84	3.571 (3)	131

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z; (iv) −x+2, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x−1, y, z; (vii) −x+1, −y, −z+1; (viii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₇H₆OS
M_r	138.18
Crystal system, space group	Triclinic, P1
Temperature (K)	92
a, b, c (Å)	6.6133 (9), 7.4894 (11), 13.3213 (16)
α, β, γ (°)	83.247 (8), 86.097 (7), 71.363 (8)
V (Å³)	620.54 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.55 × 0.28 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.617, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5251, 1522, 1264
R_int	0.040
θ_max (°)	22.1
(sin θ/λ)_max (Å⁻¹)	0.529

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.11
No. of reflections	1522
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.34

Computer programs: , APEX2 (Bruker, 2011) and SAINT (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the S1,C12,C13,C17,C18 and S2,C22,C23,C27,C28 thiophene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.99	2.52	3.473 (4)	160.3
C15—H15B···O1ⁱⁱ	0.99	2.59	3.489 (3)	150.6
C12—H12···O2ⁱⁱⁱ	0.95	2.43	3.370 (4)	168.1
C13—H13···O2^iv	0.95	2.65	3.275 (4)	124.1
C23—H23···O1^v	0.95	2.62	3.425 (4)	143.3
C24—H24A···O2^vi	0.99	2.52	3.480 (4)	163.7
C25—H25A···O2^vii	0.99	2.71	3.704 (3)	179.5
C25—H25B···Cg1^viii	0.99	2.79	3.561 (3)	135
C15—H15A···Cg4ⁱⁱⁱ	0.99	2.84	3.571 (3)	131

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z; (iv) −x+2, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x−1, y, z; (vii) −x+1, −y, −z+1; (viii) x, y−1, z.

Acknowledgements

We thank the New Economy Research Fund (grant No. UOO-X0808) for support of this work and the University of Otago for the purchase of the diffractometer.

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Volume 68| Part 2| February 2012| Pages o371-o372

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