Molecular and crystal properties of E-1,2-bis(3-methoxy-2-thienyl)ethene: static disorder in the crystal

The crystal structure of E-1,2-bis(3-methoxy-2-thienyl)ethene (C₁₂H₁₂O₂S₂) has been determined at five different temperatures, i.e. room temperature (293 ), 223, 173, 123 and 93 K. The solid-state work is complemented by the results of theoretical calculations of energies, geometries, difference electron densities and atomic charges of the free molecule. Analysis revealed static disorder caused by a higher energy conformer of the title compound, probably contaminating the crystal during its growth. The results support the contention that the electrical properties are mainly governed by the carbon backbone.

Computing details

For all compounds, data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: MolEN (Fair, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003).

(bith93) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.414 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.765 (2) Å	Cell parameters from 25 reflections
b = 11.590 (2) Å	θ = 11–21°
c = 13.172 (2) Å	µ = 0.43 mm^−1
V = 1185.4 (4) Å^3	T = 93 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf Nonius CAD4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 66.8°, θmin = 3.1°
Graphite monochromator	h = 0→20
non–profiled ω/2θ scans	k = 0→29
19748 measured reflections	l = 0→32
4866 independent reflections	3 standard reflections every 120 min
3025 reflections with I > 2σ(I)	intensity decay: 6%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.4109P] where P = (Fo^2 + 2Fc^2)/3
4866 reflections	(Δ/σ)max = 0.001
97 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.66988 (4)	0.21942 (2)	0.444458 (19)	0.02154 (7)
C5	0.73033 (15)	0.27201 (8)	0.32757 (9)	0.02217 (18)
C4	0.69138 (12)	0.19754 (8)	0.25105 (8)	0.01830 (14)
C3	0.61057 (11)	0.09560 (7)	0.28798 (7)	0.01565 (12)
C2	0.58857 (11)	0.09339 (7)	0.39199 (6)	0.01522 (12)
C6	0.50965 (12)	0.00155 (8)	0.44912 (6)	0.01596 (13)
O8	0.55748 (11)	0.00367 (6)	0.23215 (5)	0.02256 (14)
C9	0.55707 (14)	0.01912 (9)	0.12446 (7)	0.02194 (17)
H1C5	0.786 (2)	0.3459 (15)	0.3188 (14)	0.034 (4)*
H1C4	0.711 (2)	0.2134 (13)	0.1851 (14)	0.026 (4)*
H1C6	0.4678 (19)	−0.0665 (14)	0.4108 (14)	0.029 (4)*
H1C9	0.676 (2)	0.0384 (15)	0.0989 (16)	0.035 (4)*
H2C9	0.475 (2)	0.0813 (16)	0.1056 (15)	0.038 (5)*
H3C9	0.515 (2)	−0.0540 (16)	0.0974 (15)	0.037 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02813 (15)	0.01668 (10)	0.01980 (11)	−0.00173 (8)	0.00315 (8)	−0.00296 (7)
C5	0.0249 (5)	0.0166 (3)	0.0250 (4)	−0.0038 (3)	0.0018 (4)	0.0021 (3)
C4	0.0195 (4)	0.0162 (3)	0.0192 (3)	−0.0013 (3)	0.0009 (3)	0.0041 (3)
C3	0.0167 (3)	0.0140 (3)	0.0163 (3)	0.0001 (2)	−0.0014 (3)	0.0026 (2)
C2	0.0158 (3)	0.0138 (3)	0.0161 (3)	0.0006 (2)	0.0010 (3)	0.0010 (2)
C6	0.0163 (3)	0.0155 (3)	0.0161 (3)	0.0007 (3)	0.0010 (3)	0.0011 (2)
O8	0.0353 (4)	0.0169 (2)	0.0155 (2)	−0.0063 (3)	−0.0045 (3)	0.0019 (2)
C9	0.0239 (4)	0.0261 (4)	0.0159 (3)	−0.0025 (3)	0.0006 (3)	−0.0004 (3)

Geometric parameters (Å, º)

S1—C5	1.7212 (11)	C3—C2	1.3808 (12)
S1—C2	1.7349 (9)	C2—C6	1.4405 (12)
C5—C4	1.3610 (14)	C6—C6^i	1.3493 (17)
C4—C3	1.4235 (12)	O8—C9	1.4297 (12)
C3—O8	1.3586 (11)
C5—S1—C2	92.35 (5)	C3—C2—C6	125.78 (8)
C4—C5—S1	112.17 (7)	C3—C2—S1	109.55 (6)
C5—C4—C3	111.79 (9)	C6—C2—S1	124.67 (7)
O8—C3—C2	119.01 (8)	C6^i—C6—C2	125.87 (11)
O8—C3—C4	126.85 (8)	C3—O8—C9	116.07 (7)
C2—C3—C4	114.14 (8)

Symmetry code: (i) −x+1, −y, −z+1.

(bith123) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.406 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.790 (1) Å	Cell parameters from 25 reflections
b = 11.604 (1) Å	θ = 11–21°
c = 13.185 (1) Å	µ = 0.43 mm^−1
V = 1191.9 (2) Å^3	T = 123 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→15
non–profiled ω/2θ scans	k = 0→22
4890 measured reflections	l = 0→26
4890 independent reflections	3 standard reflections every 120 min
3286 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0641P)^2 + 0.2487P] where P = (Fo^2 + 2Fc^2)/3
4890 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 1.16 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.66978 (4)	0.21901 (2)	0.444491 (19)	0.02724 (7)
C5	0.73004 (14)	0.27151 (8)	0.32768 (8)	0.02771 (17)
C4	0.69125 (11)	0.19704 (7)	0.25140 (7)	0.02310 (14)
C3	0.61056 (10)	0.09537 (6)	0.28816 (6)	0.01963 (12)
C2	0.58864 (10)	0.09325 (7)	0.39199 (6)	0.01931 (12)
C6	0.50971 (11)	0.00157 (7)	0.44918 (6)	0.01995 (12)
O8	0.55756 (10)	0.00366 (6)	0.23235 (5)	0.02840 (15)
C9	0.55751 (13)	0.01860 (9)	0.12476 (7)	0.02752 (17)
H1C5	0.786 (2)	0.3451 (14)	0.3212 (13)	0.041 (4)*
H1C4	0.710 (2)	0.2135 (12)	0.1844 (13)	0.029 (4)*
H1C6	0.4674 (18)	−0.0674 (13)	0.4128 (13)	0.032 (4)*
H1C9	0.6753 (18)	0.0386 (14)	0.1000 (15)	0.038 (4)*
H2C9	0.474 (2)	0.0804 (15)	0.1042 (14)	0.045 (4)*
H3C9	0.514 (2)	−0.0579 (15)	0.1002 (14)	0.042 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03520 (13)	0.02125 (10)	0.02527 (10)	−0.00255 (8)	0.00374 (8)	−0.00366 (7)
C5	0.0318 (4)	0.0200 (3)	0.0314 (4)	−0.0046 (3)	0.0025 (3)	0.0018 (3)
C4	0.0252 (3)	0.0201 (3)	0.0240 (3)	−0.0013 (2)	0.0011 (3)	0.0050 (3)
C3	0.0210 (3)	0.0173 (3)	0.0207 (3)	0.0005 (2)	−0.0016 (2)	0.0031 (2)
C2	0.0194 (3)	0.0177 (3)	0.0209 (3)	0.0011 (2)	0.0012 (2)	0.0016 (2)
C6	0.0202 (3)	0.0192 (3)	0.0205 (3)	0.0011 (2)	0.0010 (2)	0.0018 (2)
O8	0.0439 (4)	0.0217 (3)	0.0196 (2)	−0.0071 (3)	−0.0051 (2)	0.0021 (2)
C9	0.0304 (4)	0.0331 (4)	0.0190 (3)	−0.0025 (3)	0.0007 (3)	0.0000 (3)

Geometric parameters (Å, º)

S1—C5	1.7215 (11)	C3—C2	1.3798 (11)
S1—C2	1.7345 (8)	C2—C6	1.4416 (11)
C5—C4	1.3600 (14)	C6—C6^i	1.3492 (16)
C4—C3	1.4219 (11)	O8—C9	1.4291 (11)
C3—O8	1.3581 (10)
C5—S1—C2	92.30 (4)	C3—C2—C6	125.79 (7)
C4—C5—S1	112.10 (7)	C3—C2—S1	109.62 (6)
C5—C4—C3	111.92 (8)	C6—C2—S1	124.58 (6)
O8—C3—C2	119.08 (7)	C6^i—C6—C2	125.96 (10)
O8—C3—C4	126.86 (8)	C3—O8—C9	116.29 (7)
C2—C3—C4	114.06 (8)

Symmetry code: (i) −x+1, −y, −z+1.

(bith173) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.396 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.819 (1) Å	Cell parameters from 25 reflections
b = 11.627 (1) Å	θ = 11–21°
c = 13.206 (1) Å	µ = 0.43 mm^−1
V = 1200.6 (2) Å^3	T = 173 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→13
non–profiled ω/2θ scans	k = 0→23
4795 measured reflections	l = 0→26
4795 independent reflections	3 standard reflections every 120 min
2632 reflections with I > 2σ(I)	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0858P)^2 + 0.6077P] where P = (Fo^2 + 2Fc^2)/3
4795 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.66909 (6)	0.21823 (3)	0.44455 (3)	0.03836 (12)
C5	0.7291 (2)	0.27037 (12)	0.32810 (13)	0.0388 (3)
C4	0.69070 (18)	0.19654 (11)	0.25187 (12)	0.0324 (2)
C3	0.61057 (16)	0.09509 (10)	0.28855 (9)	0.0272 (2)
C2	0.58865 (15)	0.09286 (10)	0.39225 (9)	0.0268 (2)
C6	0.50990 (16)	0.00146 (11)	0.44934 (9)	0.0274 (2)
O8	0.55792 (17)	0.00366 (9)	0.23310 (8)	0.0401 (3)
C9	0.5582 (2)	0.01778 (16)	0.12575 (11)	0.0389 (3)
H1C5	0.789 (3)	0.344 (2)	0.3222 (18)	0.054 (7)*
H1C4	0.710 (3)	0.2122 (18)	0.1844 (18)	0.042 (6)*
H1C6	0.469 (2)	−0.0657 (18)	0.4104 (17)	0.041 (5)*
H1C9	0.672 (3)	0.0356 (19)	0.1015 (19)	0.045 (6)*
H2C9	0.472 (3)	0.081 (2)	0.103 (2)	0.062 (7)*
H3C9	0.521 (3)	−0.057 (2)	0.100 (2)	0.051 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0508 (2)	0.02936 (16)	0.03497 (18)	−0.00437 (13)	0.00479 (15)	−0.00525 (11)
C5	0.0455 (8)	0.0279 (5)	0.0431 (7)	−0.0059 (5)	0.0043 (6)	0.0032 (5)
C4	0.0363 (6)	0.0282 (5)	0.0328 (5)	−0.0011 (4)	0.0019 (5)	0.0076 (4)
C3	0.0301 (5)	0.0244 (4)	0.0270 (4)	0.0006 (4)	−0.0018 (4)	0.0040 (4)
C2	0.0280 (5)	0.0242 (4)	0.0281 (5)	0.0021 (4)	0.0011 (4)	0.0019 (4)
C6	0.0277 (5)	0.0255 (4)	0.0290 (5)	0.0010 (4)	0.0014 (4)	0.0026 (4)
O8	0.0632 (7)	0.0313 (4)	0.0259 (4)	−0.0100 (5)	−0.0068 (4)	0.0027 (3)
C9	0.0433 (8)	0.0476 (8)	0.0257 (5)	−0.0037 (6)	0.0018 (5)	−0.0011 (5)

Geometric parameters (Å, º)

S1—C5	1.7184 (17)	C3—C2	1.3803 (17)
S1—C2	1.7313 (13)	C2—C6	1.4412 (17)
C5—C4	1.357 (2)	C6—C6^i	1.347 (2)
C4—C3	1.4208 (17)	O8—C9	1.4272 (17)
C3—O8	1.3549 (16)
C5—S1—C2	92.25 (7)	C3—C2—C6	125.86 (11)
C4—C5—S1	112.35 (11)	C3—C2—S1	109.57 (9)
C5—C4—C3	111.71 (13)	C6—C2—S1	124.56 (10)
O8—C3—C2	118.93 (11)	C6^i—C6—C2	125.95 (15)
O8—C3—C4	126.95 (12)	C3—O8—C9	116.50 (11)
C2—C3—C4	114.12 (12)

Symmetry code: (i) −x+1, −y, −z+1.

(bith223) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.383 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.864 (1) Å	Cell parameters from 25 reflections
b = 11.662 (1) Å	θ = 11–21°
c = 13.218 (1) Å	µ = 0.42 mm^−1
V = 1212.2 (2) Å^3	T = 223 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.261
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→15
non–profiled ω/2θ scans	k = 0→23
4981 measured reflections	l = 0→26
4980 independent reflections	3 standard reflections every 60 min
2010 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.1479P] where P = (Fo^2 + 2Fc^2)/3
4980 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.66940 (5)	0.21740 (3)	0.44459 (3)	0.05045 (13)
C5	0.7295 (2)	0.26890 (12)	0.32809 (13)	0.0505 (3)
C4	0.69074 (17)	0.19569 (11)	0.25252 (11)	0.0425 (3)
C3	0.61079 (15)	0.09460 (9)	0.28926 (9)	0.0355 (2)
C2	0.58854 (14)	0.09250 (9)	0.39235 (9)	0.0347 (2)
C6	0.51013 (16)	0.00154 (10)	0.44964 (9)	0.0357 (2)
O8	0.55803 (14)	0.00349 (8)	0.23364 (7)	0.0523 (3)
C9	0.5590 (2)	0.01661 (15)	0.12664 (11)	0.0513 (3)
H1C5	0.786 (3)	0.3420 (17)	0.3223 (16)	0.074 (6)*
H1C4	0.708 (2)	0.2115 (13)	0.1849 (14)	0.049 (5)*
H1C6	0.4677 (19)	−0.0643 (15)	0.4136 (15)	0.057 (5)*
H1C9	0.669 (2)	0.0354 (16)	0.1021 (18)	0.068 (5)*
H2C9	0.473 (3)	0.0829 (19)	0.1060 (19)	0.089 (7)*
H3C9	0.518 (2)	−0.0553 (16)	0.0988 (16)	0.063 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0664 (3)	0.03911 (17)	0.04580 (19)	−0.00582 (14)	0.00615 (15)	−0.00651 (12)
C5	0.0584 (8)	0.0357 (6)	0.0574 (8)	−0.0079 (5)	0.0059 (7)	0.0041 (5)
C4	0.0469 (7)	0.0376 (5)	0.0432 (6)	−0.0009 (5)	0.0029 (5)	0.0101 (5)
C3	0.0379 (5)	0.0320 (4)	0.0365 (5)	0.0024 (4)	−0.0021 (4)	0.0051 (4)
C2	0.0354 (5)	0.0314 (5)	0.0374 (5)	0.0033 (4)	0.0013 (4)	0.0028 (4)
C6	0.0361 (5)	0.0339 (5)	0.0370 (5)	0.0030 (4)	0.0014 (4)	0.0023 (4)
O8	0.0801 (7)	0.0416 (5)	0.0351 (4)	−0.0117 (5)	−0.0082 (4)	0.0036 (3)
C9	0.0573 (8)	0.0621 (9)	0.0346 (6)	−0.0049 (7)	0.0037 (6)	−0.0020 (6)

Geometric parameters (Å, º)

S1—C5	1.7190 (16)	C3—C2	1.3740 (17)
S1—C2	1.7328 (12)	C2—C6	1.4419 (16)
C5—C4	1.349 (2)	C6—C6^i	1.341 (2)
C4—C3	1.4216 (16)	O8—C9	1.4225 (17)
C3—O8	1.3571 (15)
C5—S1—C2	92.15 (7)	C3—C2—C6	126.04 (11)
C4—C5—S1	112.35 (10)	C3—C2—S1	109.48 (8)
C5—C4—C3	111.82 (13)	C6—C2—S1	124.48 (9)
O8—C3—C2	118.97 (10)	C6^i—C6—C2	126.28 (15)
O8—C3—C4	126.82 (12)	C3—O8—C9	116.92 (11)
C2—C3—C4	114.20 (11)

Symmetry code: (i) −x+1, −y, −z+1.

(bith293) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.364 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.935 (1) Å	Cell parameters from 25 reflections
b = 11.712 (1) Å	θ = 11–21°
c = 13.218 (1) Å	µ = 0.42 mm^−1
V = 1228.4 (2) Å^3	T = 293 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 3.1°
Graphite monochromator	h = 0→11
non–profiled ω/2θ scans	k = 0→16
1788 measured reflections	l = 0→18
1788 independent reflections	3 standard reflections every 120 min
1108 reflections with I > 2σ(I)	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 0.2085P] where P = (Fo^2 + 2Fc^2)/3
1788 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.66979 (9)	0.21582 (5)	0.44491 (5)	0.0749 (3)
C5	0.7291 (4)	0.2666 (2)	0.3288 (2)	0.0735 (7)
C4	0.6910 (3)	0.19428 (19)	0.2541 (2)	0.0623 (5)
C3	0.6112 (2)	0.09395 (16)	0.29037 (15)	0.0523 (5)
C2	0.5890 (2)	0.09193 (15)	0.39289 (15)	0.0510 (5)
C6	0.5108 (3)	0.00166 (17)	0.45021 (16)	0.0533 (5)
O8	0.5582 (3)	0.00356 (13)	0.23479 (12)	0.0768 (5)
C9	0.5602 (4)	0.0147 (3)	0.12831 (19)	0.0777 (7)
H1C5	0.785 (4)	0.331 (3)	0.323 (2)	0.088 (8)*
H1C4	0.709 (3)	0.206 (2)	0.189 (2)	0.070 (7)*
H1C6	0.469 (3)	−0.060 (2)	0.413 (2)	0.080 (7)*
H1C9	0.666 (4)	0.031 (3)	0.104 (3)	0.102 (10)*
H2C9	0.470 (5)	0.083 (3)	0.110 (3)	0.143 (13)*
H3C9	0.516 (4)	−0.054 (3)	0.101 (3)	0.111 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0985 (5)	0.0594 (4)	0.0667 (4)	−0.0087 (3)	0.0090 (3)	−0.0083 (3)
C5	0.0857 (17)	0.0537 (13)	0.0812 (16)	−0.0118 (12)	0.0076 (14)	0.0080 (12)
C4	0.0668 (13)	0.0578 (11)	0.0623 (12)	0.0017 (10)	0.0064 (10)	0.0165 (10)
C3	0.0540 (11)	0.0479 (10)	0.0549 (10)	0.0052 (8)	−0.0017 (8)	0.0066 (8)
C2	0.0505 (10)	0.0464 (9)	0.0562 (11)	0.0067 (8)	0.0019 (8)	0.0052 (8)
C6	0.0542 (10)	0.0490 (10)	0.0568 (10)	0.0052 (8)	0.0008 (9)	0.0024 (8)
O8	0.1125 (14)	0.0620 (9)	0.0559 (9)	−0.0168 (9)	−0.0092 (9)	0.0048 (7)
C9	0.0864 (18)	0.093 (2)	0.0537 (12)	−0.0095 (17)	0.0064 (13)	−0.0073 (13)

Geometric parameters (Å, º)

S1—C5	1.712 (3)	C3—C2	1.367 (3)
S1—C2	1.729 (2)	C2—C6	1.441 (3)
C5—C4	1.336 (4)	C6—C6^i	1.328 (4)
C4—C3	1.418 (3)	O8—C9	1.414 (3)
C3—O8	1.356 (2)
C5—S1—C2	92.12 (12)	C3—C2—C6	126.12 (19)
C4—C5—S1	112.35 (19)	C3—C2—S1	109.39 (14)
C5—C4—C3	112.1 (2)	C6—C2—S1	124.49 (16)
O8—C3—C2	118.94 (17)	C6^i—C6—C2	126.7 (3)
O8—C3—C4	127.0 (2)	C3—O8—C9	117.64 (19)
C2—C3—C4	114.01 (19)

Symmetry code: (i) −x+1, −y, −z+1.

(bith93dis) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.414 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.765 (2) Å	Cell parameters from 25 reflections
b = 11.590 (2) Å	θ = 11–21°
c = 13.172 (2) Å	µ = 0.43 mm^−1
V = 1185.4 (4) Å^3	T = 93 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 66.8°, θmin = 3.1°
Graphite monochromator	h = 0→20
non–profiled ω/2θ scans	k = 0→29
19748 measured reflections	l = 0→32
4866 independent reflections	3 standard reflections every 120 min
3025 reflections with I > 2σ(I)	intensity decay: 6%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.2644P] where P = (Fo^2 + 2Fc^2)/3
4866 reflections	(Δ/σ)max = 0.031
123 parameters	Δρmax = 0.46 e Å^−3
21 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.66959 (5)	0.21916 (3)	0.44440 (2)	0.02140 (8)	0.9706 (14)
C5	0.7297 (2)	0.27224 (12)	0.32774 (12)	0.0225 (3)	0.9706 (14)
C4	0.69081 (18)	0.19792 (10)	0.25091 (10)	0.01855 (19)	0.9706 (14)
C3	0.61074 (14)	0.09559 (9)	0.28779 (8)	0.01544 (15)	0.9706 (14)
C2	0.58864 (13)	0.09329 (9)	0.39184 (8)	0.01505 (15)	0.9706 (14)
C6	0.50995 (14)	0.00143 (9)	0.44921 (8)	0.01585 (16)	0.9706 (14)
O8	0.55772 (13)	0.00367 (7)	0.23198 (7)	0.02237 (17)	0.9706 (14)
C9	0.55712 (16)	0.01913 (11)	0.12434 (10)	0.0218 (2)	0.9706 (14)
H1C5	0.786 (3)	0.3462 (17)	0.3196 (16)	0.034 (5)*	0.9706 (14)
H1C4	0.712 (2)	0.2147 (15)	0.1820 (15)	0.022 (4)*	0.9706 (14)
H1C6	0.466 (2)	−0.0627 (16)	0.4098 (16)	0.025 (4)*	0.9706 (14)
H1C9	0.672 (2)	0.0381 (17)	0.0991 (18)	0.031 (5)*	0.9706 (14)
H2C9	0.475 (3)	0.0812 (18)	0.1063 (17)	0.037 (5)*	0.9706 (14)
H3C9	0.516 (3)	−0.0537 (19)	0.0972 (19)	0.040 (5)*	0.9706 (14)
S21	0.7039 (18)	0.2502 (12)	0.4513 (9)	0.02140 (8)	0.0294 (14)
C25	0.758 (10)	0.262 (5)	0.325 (2)	0.0225 (3)	0.0294 (14)
H25	0.8238	0.3225	0.2999	0.027*	0.0294 (14)
C24	0.698 (6)	0.177 (3)	0.263 (2)	0.01855 (19)	0.0294 (14)
H24	0.7166	0.1710	0.1937	0.022*	0.0294 (14)
C23	0.599 (5)	0.096 (2)	0.3248 (19)	0.01544 (15)	0.0294 (14)
C22	0.599 (4)	0.123 (2)	0.4243 (19)	0.01505 (15)	0.0294 (14)
C26	0.512 (3)	0.035 (3)	0.4902 (19)	0.01585 (16)	0.0294 (14)
H26	0.4466	0.0804	0.5343	0.019*	0.0294 (14)
O28	0.528 (4)	0.006 (2)	0.273 (2)	0.02237 (17)	0.0294 (14)
C29	0.552 (6)	0.008 (4)	0.167 (2)	0.0218 (2)	0.0294 (14)
H29A	0.5079	−0.0623	0.1379	0.033*	0.0294 (14)
H29B	0.6731	0.0138	0.1519	0.033*	0.0294 (14)
H29C	0.4928	0.0726	0.1382	0.033*	0.0294 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02786 (18)	0.01620 (12)	0.02014 (14)	−0.00277 (11)	0.00293 (10)	−0.00335 (10)
C5	0.0248 (8)	0.0168 (5)	0.0258 (5)	−0.0029 (5)	0.0020 (5)	0.0019 (4)
C4	0.0199 (4)	0.0162 (4)	0.0196 (4)	−0.0010 (4)	0.0006 (4)	0.0049 (4)
C3	0.0166 (4)	0.0143 (3)	0.0154 (3)	0.0002 (3)	−0.0011 (3)	0.0026 (3)
C2	0.0158 (4)	0.0136 (3)	0.0158 (3)	0.0007 (3)	0.0008 (3)	0.0004 (3)
C6	0.0161 (4)	0.0154 (3)	0.0160 (4)	0.0007 (3)	0.0010 (3)	0.0006 (3)
O8	0.0351 (5)	0.0172 (3)	0.0149 (3)	−0.0062 (3)	−0.0039 (3)	0.0019 (3)
C9	0.0239 (5)	0.0264 (5)	0.0151 (4)	−0.0025 (4)	0.0008 (4)	−0.0003 (4)
S21	0.02786 (18)	0.01620 (12)	0.02014 (14)	−0.00277 (11)	0.00293 (10)	−0.00335 (10)
C25	0.0248 (8)	0.0168 (5)	0.0258 (5)	−0.0029 (5)	0.0020 (5)	0.0019 (4)
C24	0.0199 (4)	0.0162 (4)	0.0196 (4)	−0.0010 (4)	0.0006 (4)	0.0049 (4)
C23	0.0166 (4)	0.0143 (3)	0.0154 (3)	0.0002 (3)	−0.0011 (3)	0.0026 (3)
C22	0.0158 (4)	0.0136 (3)	0.0158 (3)	0.0007 (3)	0.0008 (3)	0.0004 (3)
C26	0.0161 (4)	0.0154 (3)	0.0160 (4)	0.0007 (3)	0.0010 (3)	0.0006 (3)
O28	0.0351 (5)	0.0172 (3)	0.0149 (3)	−0.0062 (3)	−0.0039 (3)	0.0019 (3)
C29	0.0239 (5)	0.0264 (5)	0.0151 (4)	−0.0025 (4)	0.0008 (4)	−0.0003 (4)

Geometric parameters (Å, º)

S1—C5	1.7199 (15)	S21—C22	1.72 (2)
S1—C2	1.7328 (11)	S21—C25	1.73 (2)
C5—C4	1.3628 (18)	C25—C24	1.36 (2)
C4—C3	1.4245 (15)	C24—C23	1.46 (2)
C3—O8	1.3583 (13)	C23—C22	1.35 (2)
C3—C2	1.3815 (15)	C23—O28	1.36 (2)
C2—C6	1.4414 (14)	C22—C26	1.50 (2)
C6—C6^i	1.347 (2)	C26—C26^i	0.88 (5)
O8—C9	1.4291 (14)	O28—C29	1.41 (2)
C5—S1—C2	92.45 (6)	C22—S21—C25	88.9 (14)
C4—C5—S1	112.16 (10)	C24—C25—S21	116 (2)
C5—C4—C3	111.70 (11)	C25—C24—C23	108 (2)
O8—C3—C2	118.96 (9)	C22—C23—O28	132 (2)
O8—C3—C4	126.92 (10)	C22—C23—C24	113.2 (19)
C2—C3—C4	114.12 (10)	O28—C23—C24	115 (2)
C3—C2—C6	125.94 (10)	C23—C22—C26	114 (2)
C3—C2—S1	109.57 (7)	C23—C22—S21	113.4 (16)
C6—C2—S1	124.48 (8)	C26—C22—S21	132.4 (19)
C6^i—C6—C2	125.97 (13)	C26^i—C26—C22	154 (6)
C3—O8—C9	116.08 (9)	C23—O28—C29	116 (2)

Symmetry code: (i) −x+1, −y, −z+1.

(bith123dis) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.406 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.790 (1) Å	Cell parameters from 25 reflections
b = 11.604 (2) Å	θ = 11–21°
c = 13.185 (2) Å	µ = 0.43 mm^−1
V = 1191.9 (3) Å^3	T = 123 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→15
non–profiled ω/2θ scans	k = 0→22
4890 measured reflections	l = 0→26
4890 independent reflections	3 standard reflections every 120 min
3286 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 0.089P] where P = (Fo^2 + 2Fc^2)/3
4890 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.48 e Å^−3
19 restraints	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.66954 (3)	0.21881 (2)	0.444444 (16)	0.02691 (6)	0.9701 (9)
C5	0.72936 (14)	0.27164 (9)	0.32779 (8)	0.0280 (2)	0.9701 (9)
C4	0.69162 (14)	0.19722 (9)	0.25117 (7)	0.02339 (15)	0.9701 (9)
C3	0.61072 (9)	0.09536 (5)	0.28802 (5)	0.01929 (10)	0.9701 (9)
C2	0.58861 (8)	0.09310 (6)	0.39194 (5)	0.01897 (10)	0.9701 (9)
C6	0.50978 (9)	0.00157 (6)	0.44918 (5)	0.01969 (10)	0.9701 (9)
O8	0.55775 (9)	0.00365 (5)	0.23223 (4)	0.02811 (12)	0.9701 (9)
C9	0.55760 (11)	0.01859 (8)	0.12474 (6)	0.02716 (14)	0.9701 (9)
H1C5	0.7877 (17)	0.3463 (11)	0.3225 (10)	0.040 (3)*	0.9701 (9)
H1C4	0.7107 (15)	0.2133 (9)	0.1819 (10)	0.026 (3)*	0.9701 (9)
H1C6	0.4668 (13)	−0.0624 (10)	0.4096 (10)	0.026 (3)*	0.9701 (9)
H1C9	0.6720 (15)	0.0372 (11)	0.1002 (11)	0.036 (3)*	0.9701 (9)
H2C9	0.4751 (17)	0.0801 (12)	0.1053 (11)	0.044 (4)*	0.9701 (9)
H3C9	0.5151 (17)	−0.0558 (12)	0.0993 (12)	0.047 (4)*	0.9701 (9)
S21	0.7071 (11)	0.2512 (8)	0.4519 (6)	0.02691 (6)	0.0299 (9)
C25	0.757 (7)	0.264 (4)	0.3242 (16)	0.0280 (2)	0.0299 (9)
H25	0.8363	0.3168	0.2997	0.034*	0.0299 (9)
C24	0.668 (6)	0.190 (3)	0.2630 (17)	0.02339 (15)	0.0299 (9)
H24	0.6528	0.1977	0.1934	0.028*	0.0299 (9)
C23	0.603 (3)	0.0971 (15)	0.3270 (12)	0.01929 (10)	0.0299 (9)
C22	0.601 (3)	0.1231 (14)	0.4248 (12)	0.01897 (10)	0.0299 (9)
C26	0.5375 (18)	0.0480 (16)	0.5059 (11)	0.01969 (10)	0.0299 (9)
H26	0.5536	0.0732	0.5722	0.024*	0.0299 (9)
O28	0.534 (3)	0.0081 (15)	0.2731 (13)	0.02811 (12)	0.0299 (9)
C29	0.558 (4)	0.003 (2)	0.1673 (15)	0.02716 (14)	0.0299 (9)
H29A	0.5118	−0.0684	0.1420	0.041*	0.0299 (9)
H29B	0.6785	0.0064	0.1523	0.041*	0.0299 (9)
H29C	0.5004	0.0663	0.1357	0.041*	0.0299 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03485 (11)	0.02049 (9)	0.02539 (9)	−0.00346 (7)	0.00349 (7)	−0.00401 (6)
C5	0.0316 (6)	0.0204 (3)	0.0319 (3)	−0.0039 (4)	0.0027 (3)	0.0018 (2)
C4	0.0251 (4)	0.0208 (3)	0.0243 (3)	−0.0015 (2)	0.0015 (3)	0.0056 (2)
C3	0.0209 (2)	0.0175 (2)	0.0194 (2)	0.00061 (19)	−0.0016 (2)	0.00302 (19)
C2	0.0194 (2)	0.0174 (2)	0.0201 (2)	0.00110 (19)	0.0010 (2)	0.00101 (18)
C6	0.0196 (2)	0.0191 (2)	0.0204 (2)	0.00111 (19)	0.0010 (2)	0.00178 (19)
O8	0.0438 (3)	0.0219 (2)	0.0186 (2)	−0.0071 (2)	−0.0047 (2)	0.00211 (17)
C9	0.0302 (3)	0.0327 (4)	0.0186 (3)	−0.0022 (3)	0.0008 (2)	0.0001 (2)
S21	0.03485 (11)	0.02049 (9)	0.02539 (9)	−0.00346 (7)	0.00349 (7)	−0.00401 (6)
C25	0.0316 (6)	0.0204 (3)	0.0319 (3)	−0.0039 (4)	0.0027 (3)	0.0018 (2)
C24	0.0251 (4)	0.0208 (3)	0.0243 (3)	−0.0015 (2)	0.0015 (3)	0.0056 (2)
C23	0.0209 (2)	0.0175 (2)	0.0194 (2)	0.00061 (19)	−0.0016 (2)	0.00302 (19)
C22	0.0194 (2)	0.0174 (2)	0.0201 (2)	0.00110 (19)	0.0010 (2)	0.00101 (18)
C26	0.0196 (2)	0.0191 (2)	0.0204 (2)	0.00111 (19)	0.0010 (2)	0.00178 (19)
O28	0.0438 (3)	0.0219 (2)	0.0186 (2)	−0.0071 (2)	−0.0047 (2)	0.00211 (17)
C29	0.0302 (3)	0.0327 (4)	0.0186 (3)	−0.0022 (3)	0.0008 (2)	0.0001 (2)

Geometric parameters (Å, º)

S1—C5	1.7200 (10)	S21—C22	1.737 (14)
S1—C2	1.7334 (7)	S21—C25	1.733 (18)
C5—C4	1.3612 (12)	C25—C24	1.362 (18)
C4—C3	1.4249 (10)	C24—C23	1.462 (17)
C3—O8	1.3579 (9)	C23—C22	1.324 (15)
C3—C2	1.3812 (10)	C23—O28	1.365 (15)
C2—C6	1.4404 (9)	C22—C26	1.466 (15)
C6—C6^i	1.3493 (13)	C26—C26^i	1.27 (3)
O8—C9	1.4278 (9)	O28—C29	1.408 (17)
C5—S1—C2	92.37 (4)	C22—S21—C25	88.8 (10)
C4—C5—S1	112.27 (7)	C24—C25—S21	114.2 (17)
C5—C4—C3	111.64 (8)	C25—C24—C23	107.3 (18)
O8—C3—C2	118.99 (6)	C22—C23—O28	132.4 (16)
O8—C3—C4	126.85 (7)	C22—C23—C24	113.4 (14)
C2—C3—C4	114.15 (7)	O28—C23—C24	113.4 (15)
C3—C2—C6	125.94 (6)	C23—C22—C26	125.4 (14)
C3—C2—S1	109.56 (5)	C23—C22—S21	112.9 (11)
C6—C2—S1	124.50 (5)	C26—C22—S21	121.3 (12)
C6^i—C6—C2	126.04 (8)	C26^i—C26—C22	126.1 (19)
C3—O8—C9	116.29 (6)	C23—O28—C29	119.7 (17)

Symmetry code: (i) −x+1, −y, −z+1.

(bith173dis) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.396 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.819 (1) Å	Cell parameters from 25 reflections
b = 11.627 (1) Å	θ = 11–21°
c = 13.206 (1) Å	µ = 0.43 mm^−1
V = 1200.6 (2) Å^3	T = 173 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→13
non–profiled ω/2θ scans	k = 0→23
4795 measured reflections	l = 0→26
4795 independent reflections	3 standard reflections every 120 min
2632 reflections with I > 2σ(I)	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1114P)^2 + 0.0829P] where P = (Fo^2 + 2Fc^2)/3
4795 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.59 e Å^−3
19 restraints	Δρmin = −0.54 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.66887 (7)	0.21806 (4)	0.44457 (3)	0.03787 (12)	0.9829 (18)
C5	0.7287 (2)	0.27049 (12)	0.32818 (14)	0.0386 (3)	0.9829 (18)
C4	0.6909 (2)	0.19666 (11)	0.25173 (11)	0.0323 (2)	0.9829 (18)
C3	0.61077 (15)	0.09511 (9)	0.28845 (9)	0.0269 (2)	0.9829 (18)
C2	0.58854 (14)	0.09269 (9)	0.39210 (9)	0.02632 (19)	0.9829 (18)
C6	0.50984 (15)	0.00152 (10)	0.44933 (8)	0.0269 (2)	0.9829 (18)
O8	0.55815 (16)	0.00374 (9)	0.23305 (8)	0.0397 (3)	0.9829 (18)
C9	0.5583 (2)	0.01786 (14)	0.12578 (10)	0.0382 (3)	0.9829 (18)
H1C5	0.792 (3)	0.3437 (17)	0.3233 (16)	0.045 (5)*	0.9829 (18)
H1C4	0.708 (3)	0.2142 (16)	0.1847 (18)	0.038 (5)*	0.9829 (18)
H1C6	0.472 (2)	−0.0611 (16)	0.4112 (17)	0.038 (5)*	0.9829 (18)
H1C9	0.670 (2)	0.0339 (17)	0.1017 (18)	0.040 (5)*	0.9829 (18)
H2C9	0.474 (3)	0.079 (2)	0.101 (2)	0.063 (7)*	0.9829 (18)
H3C9	0.522 (3)	−0.0565 (19)	0.097 (2)	0.052 (6)*	0.9829 (18)
S21	0.703 (4)	0.248 (2)	0.4419 (19)	0.03787 (12)	0.0171 (18)
C25	0.764 (14)	0.253 (7)	0.317 (3)	0.0386 (3)	0.0171 (18)
H25	0.8441	0.3043	0.2916	0.046*	0.0171 (18)
C24	0.683 (14)	0.174 (6)	0.259 (3)	0.0323 (2)	0.0171 (18)
H24	0.6856	0.1721	0.1886	0.039*	0.0171 (18)
C23	0.593 (9)	0.093 (4)	0.321 (3)	0.0269 (2)	0.0171 (18)
C22	0.593 (8)	0.119 (4)	0.422 (2)	0.02632 (19)	0.0171 (18)
C26	0.541 (4)	0.044 (4)	0.504 (3)	0.0269 (2)	0.0171 (18)
H26	0.5735	0.0653	0.5689	0.032*	0.0171 (18)
O28	0.537 (9)	−0.005 (4)	0.276 (3)	0.0397 (3)	0.0171 (18)
C29	0.563 (12)	−0.009 (7)	0.168 (4)	0.0382 (3)	0.0171 (18)
H29A	0.5173	−0.0797	0.1416	0.057*	0.0171 (18)
H29B	0.6829	−0.0048	0.1533	0.057*	0.0171 (18)
H29C	0.5053	0.0547	0.1366	0.057*	0.0171 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0502 (2)	0.02854 (18)	0.03487 (18)	−0.00500 (14)	0.00488 (14)	−0.00517 (12)
C5	0.0448 (8)	0.0278 (6)	0.0431 (7)	−0.0055 (5)	0.0047 (6)	0.0029 (5)
C4	0.0366 (6)	0.0276 (5)	0.0328 (5)	−0.0013 (5)	0.0020 (4)	0.0081 (4)
C3	0.0301 (5)	0.0244 (4)	0.0260 (4)	0.0006 (4)	−0.0016 (4)	0.0042 (3)
C2	0.0279 (4)	0.0239 (4)	0.0271 (4)	0.0022 (4)	0.0012 (4)	0.0014 (3)
C6	0.0271 (4)	0.0252 (4)	0.0284 (4)	0.0012 (3)	0.0014 (4)	0.0024 (3)
O8	0.0629 (7)	0.0312 (4)	0.0249 (4)	−0.0100 (4)	−0.0065 (4)	0.0030 (3)
C9	0.0428 (7)	0.0468 (7)	0.0251 (5)	−0.0037 (6)	0.0017 (5)	−0.0009 (5)
S21	0.0502 (2)	0.02854 (18)	0.03487 (18)	−0.00500 (14)	0.00488 (14)	−0.00517 (12)
C25	0.0448 (8)	0.0278 (6)	0.0431 (7)	−0.0055 (5)	0.0047 (6)	0.0029 (5)
C24	0.0366 (6)	0.0276 (5)	0.0328 (5)	−0.0013 (5)	0.0020 (4)	0.0081 (4)
C23	0.0301 (5)	0.0244 (4)	0.0260 (4)	0.0006 (4)	−0.0016 (4)	0.0042 (3)
C22	0.0279 (4)	0.0239 (4)	0.0271 (4)	0.0022 (4)	0.0012 (4)	0.0014 (3)
C26	0.0271 (4)	0.0252 (4)	0.0284 (4)	0.0012 (3)	0.0014 (4)	0.0024 (3)
O28	0.0629 (7)	0.0312 (4)	0.0249 (4)	−0.0100 (4)	−0.0065 (4)	0.0030 (3)
C29	0.0428 (7)	0.0468 (7)	0.0251 (5)	−0.0037 (6)	0.0017 (5)	−0.0009 (5)

Geometric parameters (Å, º)

S1—C5	1.7185 (17)	S21—C22	1.745 (18)
S1—C2	1.7319 (12)	S21—C25	1.722 (19)
C5—C4	1.358 (2)	C25—C24	1.350 (19)
C4—C3	1.4220 (17)	C24—C23	1.432 (18)
C3—O8	1.3539 (15)	C23—C22	1.360 (17)
C3—C2	1.3801 (16)	C23—O28	1.359 (18)
C2—C6	1.4399 (15)	C22—C26	1.453 (18)
C6—C6^i	1.348 (2)	C26—C26^i	1.21 (7)
O8—C9	1.4262 (16)	O28—C29	1.44 (2)
C5—S1—C2	92.26 (6)	C22—S21—C25	91.0 (13)
C4—C5—S1	112.42 (10)	C24—C25—S21	113 (2)
C5—C4—C3	111.55 (12)	C25—C24—C23	110 (2)
O8—C3—C2	118.79 (10)	C22—C23—O28	128 (2)
O8—C3—C4	126.95 (11)	C22—C23—C24	114.5 (18)
C2—C3—C4	114.25 (11)	O28—C23—C24	117 (2)
C3—C2—C6	126.11 (11)	C23—C22—C26	126 (2)
C3—C2—S1	109.51 (8)	C23—C22—S21	109.9 (15)
C6—C2—S1	124.37 (9)	C26—C22—S21	123 (2)
C6^i—C6—C2	126.11 (14)	C26^i—C26—C22	127 (4)
C3—O8—C9	116.50 (10)	C23—O28—C29	115 (3)

Symmetry code: (i) −x+1, −y, −z+1.

(bith223dis) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.383 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.864 (1) Å	Cell parameters from 25 reflections
b = 11.662 (1) Å	θ = 11–21°
c = 13.218 (1) Å	µ = 0.42 mm^−1
V = 1212.2 (2) Å^3	T = 223 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.261
Radiation source: fine-focus sealed tube	θmax = 44.9°, θmin = 3.1°
Graphite monochromator	h = 0→15
non–profiled ω/2θ scans	k = 0→23
4981 measured reflections	l = 0→26
4980 independent reflections	3 standard reflections every 60 min
2010 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.3816P] where P = (Fo^2 + 2Fc^2)/3
4980 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.27 e Å^−3
19 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.66899 (7)	0.21702 (5)	0.44453 (3)	0.05024 (13)	0.972 (2)
C5	0.7290 (14)	0.2690 (5)	0.32820 (19)	0.0511 (6)	0.972 (2)
C4	0.6905 (3)	0.19605 (13)	0.25237 (12)	0.0428 (3)	0.972 (2)
C3	0.61082 (16)	0.09467 (10)	0.28892 (10)	0.0350 (2)	0.972 (2)
C2	0.58870 (15)	0.09226 (10)	0.39214 (9)	0.0340 (2)	0.972 (2)
C6	0.51017 (16)	0.00146 (10)	0.44960 (9)	0.0351 (2)	0.972 (2)
O8	0.55816 (16)	0.00349 (9)	0.23337 (9)	0.0515 (3)	0.972 (2)
C9	0.5590 (2)	0.01672 (15)	0.12636 (12)	0.0508 (3)	0.972 (2)
H1C5	0.787 (3)	0.3421 (17)	0.3217 (14)	0.069 (5)*	0.972 (2)
H1C4	0.710 (2)	0.2115 (13)	0.1835 (12)	0.047 (4)*	0.972 (2)
H1C6	0.4686 (18)	−0.0615 (13)	0.4104 (13)	0.049 (4)*	0.972 (2)
H1C9	0.669 (2)	0.0343 (15)	0.1027 (15)	0.065 (5)*	0.972 (2)
H2C9	0.476 (3)	0.0835 (17)	0.1076 (16)	0.078 (6)*	0.972 (2)
H3C9	0.517 (2)	−0.0542 (16)	0.0989 (15)	0.069 (5)*	0.972 (2)
S21	0.699 (3)	0.2485 (17)	0.4498 (14)	0.05024 (13)	0.028 (2)
C25	0.74 (5)	0.270 (18)	0.323 (5)	0.0511 (6)	0.028 (2)
H25	0.7884	0.3361	0.2974	0.061*	0.028 (2)
C24	0.692 (13)	0.180 (5)	0.266 (3)	0.0428 (3)	0.028 (2)
H24	0.7101	0.1748	0.1961	0.051*	0.028 (2)
C23	0.610 (6)	0.092 (3)	0.325 (2)	0.0350 (2)	0.028 (2)
C22	0.590 (5)	0.122 (3)	0.4232 (19)	0.0340 (2)	0.028 (2)
C26	0.543 (3)	0.040 (3)	0.503 (2)	0.0351 (2)	0.028 (2)
H26	0.5887	0.0543	0.5662	0.042*	0.028 (2)
O28	0.537 (6)	0.003 (3)	0.274 (2)	0.0515 (3)	0.028 (2)
C29	0.566 (8)	0.000 (5)	0.168 (3)	0.0508 (3)	0.028 (2)
H29A	0.5214	−0.0694	0.1404	0.076*	0.028 (2)
H29B	0.6863	0.0042	0.1553	0.076*	0.028 (2)
H29C	0.5110	0.0647	0.1368	0.076*	0.028 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0663 (3)	0.0379 (2)	0.04646 (19)	−0.00717 (18)	0.00597 (17)	−0.00695 (16)
C5	0.059 (2)	0.0368 (6)	0.0576 (8)	−0.0078 (7)	0.0062 (9)	0.0046 (7)
C4	0.0469 (7)	0.0383 (7)	0.0431 (6)	−0.0005 (7)	0.0026 (6)	0.0108 (5)
C3	0.0378 (5)	0.0326 (5)	0.0346 (5)	0.0025 (4)	−0.0022 (5)	0.0053 (4)
C2	0.0353 (5)	0.0307 (5)	0.0359 (5)	0.0033 (4)	0.0015 (4)	0.0016 (4)
C6	0.0355 (5)	0.0333 (5)	0.0366 (5)	0.0025 (4)	0.0015 (4)	0.0022 (4)
O8	0.0798 (7)	0.0422 (4)	0.0326 (5)	−0.0119 (5)	−0.0072 (5)	0.0036 (4)
C9	0.0574 (8)	0.0616 (9)	0.0334 (6)	−0.0048 (7)	0.0034 (6)	−0.0013 (6)
S21	0.0663 (3)	0.0379 (2)	0.04646 (19)	−0.00717 (18)	0.00597 (17)	−0.00695 (16)
C25	0.059 (2)	0.0368 (6)	0.0576 (8)	−0.0078 (7)	0.0062 (9)	0.0046 (7)
C24	0.0469 (7)	0.0383 (7)	0.0431 (6)	−0.0005 (7)	0.0026 (6)	0.0108 (5)
C23	0.0378 (5)	0.0326 (5)	0.0346 (5)	0.0025 (4)	−0.0022 (5)	0.0053 (4)
C22	0.0353 (5)	0.0307 (5)	0.0359 (5)	0.0033 (4)	0.0015 (4)	0.0016 (4)
C26	0.0355 (5)	0.0333 (5)	0.0366 (5)	0.0025 (4)	0.0015 (4)	0.0022 (4)
O28	0.0798 (7)	0.0422 (4)	0.0326 (5)	−0.0119 (5)	−0.0072 (5)	0.0036 (4)
C29	0.0574 (8)	0.0616 (9)	0.0334 (6)	−0.0048 (7)	0.0034 (6)	−0.0013 (6)

Geometric parameters (Å, º)

S1—C5	1.7187 (17)	S21—C25	1.720 (19)
S1—C2	1.7306 (12)	S21—C22	1.741 (17)
C5—C4	1.349 (2)	C25—C24	1.349 (19)
C4—C3	1.4227 (17)	C24—C23	1.444 (18)
C3—O8	1.3569 (15)	C23—C22	1.347 (17)
C3—C2	1.3758 (17)	C23—O28	1.369 (17)
C2—C6	1.4421 (16)	C22—C26	1.470 (17)
C6—C6^i	1.342 (2)	C26—C26^i	1.15 (5)
O8—C9	1.4229 (17)	O28—C29	1.422 (19)
C5—S1—C2	92.20 (7)	C25—S21—C22	90.9 (17)
C4—C5—S1	112.40 (12)	C24—C25—S21	113 (2)
C5—C4—C3	111.74 (14)	C25—C24—C23	111.3 (19)
O8—C3—C2	118.82 (10)	C22—C23—O28	128 (2)
O8—C3—C4	127.01 (12)	C22—C23—C24	113.2 (17)
C2—C3—C4	114.16 (11)	O28—C23—C24	117 (2)
C3—C2—C6	126.26 (12)	C23—C22—C26	123 (2)
C3—C2—S1	109.49 (8)	C23—C22—S21	110.8 (15)
C6—C2—S1	124.25 (10)	C26—C22—S21	122.2 (19)
C6^i—C6—C2	126.33 (15)	C26^i—C26—C22	129 (3)
C3—O8—C9	116.84 (11)	C23—O28—C29	116 (3)

Symmetry code: (i) −x+1, −y, −z+1.

(bith293dis) E-1,2-bis(3-methoxy-2-thienyl)ethene

Crystal data

C12H12O2S2	Dx = 1.364 Mg m^−3
Mr = 252.34	Melting point: 121-123°C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.935 (1) Å	Cell parameters from 25 reflections
b = 11.712 (1) Å	θ = 11–21°
c = 13.218 (1) Å	µ = 0.42 mm^−1
V = 1228.4 (2) Å^3	T = 293 K
Z = 4	Octahedral, red-brown
F(000) = 528	0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 3.1°
Graphite monochromator	h = 0→11
non–profiled ω/2θ scans	k = 0→16
1788 measured reflections	l = 0→18
1788 independent reflections	3 standard reflections every 120 min
1108 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.3816P] where P = (Fo^2 + 2Fc^2)/3
1788 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.19 e Å^−3
19 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.66915 (13)	0.21528 (10)	0.44483 (6)	0.0744 (3)	0.964 (4)
C5	0.7277 (4)	0.2668 (2)	0.3288 (2)	0.0729 (9)	0.964 (4)
C4	0.6905 (5)	0.1948 (2)	0.25376 (19)	0.0624 (7)	0.964 (4)
C3	0.6112 (3)	0.09403 (17)	0.28967 (16)	0.0513 (5)	0.964 (4)
C2	0.5892 (3)	0.09143 (16)	0.39253 (16)	0.0492 (5)	0.964 (4)
C6	0.5110 (3)	0.00169 (16)	0.45004 (16)	0.0516 (5)	0.964 (4)
O8	0.5586 (3)	0.00360 (14)	0.23436 (15)	0.0753 (5)	0.964 (4)
C9	0.5603 (4)	0.0149 (3)	0.1278 (2)	0.0768 (8)	0.964 (4)
H1C5	0.782 (3)	0.335 (2)	0.3226 (18)	0.090 (8)*	0.964 (4)
H1C4	0.711 (3)	0.2089 (18)	0.1865 (17)	0.068 (6)*	0.964 (4)
H1C6	0.473 (3)	−0.0590 (18)	0.4107 (16)	0.066 (6)*	0.964 (4)
H1C9	0.662 (3)	0.035 (2)	0.105 (2)	0.097 (9)*	0.964 (4)
H2C9	0.471 (4)	0.080 (3)	0.110 (3)	0.130 (11)*	0.964 (4)
H3C9	0.517 (4)	−0.056 (2)	0.102 (2)	0.107 (10)*	0.964 (4)
S21	0.700 (4)	0.250 (2)	0.4477 (19)	0.0744 (3)	0.036 (4)
C25	0.777 (12)	0.254 (6)	0.326 (3)	0.0729 (9)	0.036 (4)
H25	0.8617	0.3028	0.3046	0.087*	0.036 (4)
C24	0.701 (16)	0.178 (7)	0.267 (3)	0.0624 (7)	0.036 (4)
H24	0.7025	0.1796	0.1964	0.075*	0.036 (4)
C23	0.615 (9)	0.092 (4)	0.325 (3)	0.0513 (5)	0.036 (4)
C22	0.594 (7)	0.124 (3)	0.424 (2)	0.0492 (5)	0.036 (4)
C26	0.545 (3)	0.045 (4)	0.504 (3)	0.0516 (5)	0.036 (4)
H26	0.5834	0.0633	0.5684	0.062*	0.036 (4)
O28	0.536 (7)	0.004 (4)	0.278 (3)	0.0753 (5)	0.036 (4)
C29	0.555 (11)	−0.005 (7)	0.173 (4)	0.0768 (8)	0.036 (4)
H29A	0.5063	−0.0760	0.1505	0.115*	0.036 (4)
H29B	0.6725	−0.0039	0.1561	0.115*	0.036 (4)
H29C	0.4987	0.0572	0.1403	0.115*	0.036 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0983 (6)	0.0573 (4)	0.0677 (3)	−0.0109 (4)	0.0089 (3)	−0.0087 (3)
C5	0.082 (2)	0.0544 (14)	0.0817 (14)	−0.0098 (14)	0.0082 (14)	0.0074 (11)
C4	0.0662 (14)	0.0586 (14)	0.0624 (12)	0.0022 (14)	0.0055 (12)	0.0172 (11)
C3	0.0539 (10)	0.0482 (9)	0.0517 (10)	0.0052 (8)	−0.0021 (11)	0.0066 (9)
C2	0.0502 (10)	0.0449 (10)	0.0525 (12)	0.0063 (9)	0.0020 (9)	0.0028 (8)
C6	0.0526 (10)	0.0475 (10)	0.0548 (10)	0.0039 (8)	0.0010 (9)	0.0019 (9)
O8	0.1133 (14)	0.0636 (8)	0.0492 (10)	−0.0169 (9)	−0.0077 (10)	0.0043 (7)
C9	0.0870 (18)	0.093 (2)	0.0508 (12)	−0.0103 (17)	0.0069 (14)	−0.0052 (13)
S21	0.0983 (6)	0.0573 (4)	0.0677 (3)	−0.0109 (4)	0.0089 (3)	−0.0087 (3)
C25	0.082 (2)	0.0544 (14)	0.0817 (14)	−0.0098 (14)	0.0082 (14)	0.0074 (11)
C24	0.0662 (14)	0.0586 (14)	0.0624 (12)	0.0022 (14)	0.0055 (12)	0.0172 (11)
C23	0.0539 (10)	0.0482 (9)	0.0517 (10)	0.0052 (8)	−0.0021 (11)	0.0066 (9)
C22	0.0502 (10)	0.0449 (10)	0.0525 (12)	0.0063 (9)	0.0020 (9)	0.0028 (8)
C26	0.0526 (10)	0.0475 (10)	0.0548 (10)	0.0039 (8)	0.0010 (9)	0.0019 (9)
O28	0.1133 (14)	0.0636 (8)	0.0492 (10)	−0.0169 (9)	−0.0077 (10)	0.0043 (7)
C29	0.0870 (18)	0.093 (2)	0.0508 (12)	−0.0103 (17)	0.0069 (14)	−0.0052 (13)

Geometric parameters (Å, º)

S1—C5	1.713 (3)	S21—C22	1.733 (18)
S1—C2	1.7276 (19)	S21—C25	1.716 (19)
C5—C4	1.335 (3)	C25—C24	1.33 (2)
C4—C3	1.419 (3)	C24—C23	1.434 (19)
C3—O8	1.353 (2)	C23—C22	1.360 (18)
C3—C2	1.371 (3)	C23—O28	1.358 (18)
C2—C6	1.438 (3)	C22—C26	1.456 (18)
C6—C6^i	1.333 (4)	C26—C26^i	1.29 (6)
O8—C9	1.414 (3)	O28—C29	1.40 (2)
C5—S1—C2	92.13 (11)	C22—S21—C25	91.1 (13)
C4—C5—S1	112.48 (19)	C24—C25—S21	112 (2)
C5—C4—C3	112.0 (2)	C25—C24—C23	111 (2)
O8—C3—C2	118.61 (17)	C22—C23—O28	126 (3)
O8—C3—C4	127.39 (19)	C22—C23—C24	113 (2)
C2—C3—C4	114.00 (19)	O28—C23—C24	120 (2)
C3—C2—C6	126.55 (19)	C23—C22—C26	124 (3)
C3—C2—S1	109.34 (14)	C23—C22—S21	110.4 (15)
C6—C2—S1	124.10 (16)	C26—C22—S21	122 (2)
C6^i—C6—C2	127.0 (2)	C26^i—C26—C22	128 (3)
C3—O8—C9	117.48 (18)	C23—O28—C29	118 (3)

Symmetry code: (i) −x+1, −y, −z+1.