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.
Supporting information
CCDC references: 227651; 227652; 227653; 227654; 227655; 227656; 227657; 227658; 227659; 227660
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
top
Crystal data top
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) Å3 | T = 93 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.4109P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 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) | C6i—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
top
Crystal data top
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) Å3 | T = 123 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2487P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 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) | C6i—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
top
Crystal data top
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) Å3 | T = 173 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0858P)2 + 0.6077P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 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) | C6i—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
top
Crystal data top
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) Å3 | T = 223 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0676P)2 + 0.1479P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 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) | C6i—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
top
Crystal data top
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) Å3 | T = 293 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0743P)2 + 0.2085P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 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) | C6i—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
top
Crystal data top
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) Å3 | T = 93 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2644P] where P = (Fo2 + 2Fc2)/3 |
4866 reflections | (Δ/σ)max = 0.031 |
123 parameters | Δρmax = 0.46 e Å−3 |
21 restraints | |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 1.347 (2) | C26—C26i | 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) |
C6i—C6—C2 | 125.97 (13) | C26i—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
top
Crystal data top
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) Å3 | T = 123 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.089P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 1.3493 (13) | C26—C26i | 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) |
C6i—C6—C2 | 126.04 (8) | C26i—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
top
Crystal data top
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) Å3 | T = 173 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1114P)2 + 0.0829P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 1.348 (2) | C26—C26i | 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) |
C6i—C6—C2 | 126.11 (14) | C26i—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
top
Crystal data top
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) Å3 | T = 223 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.3816P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 1.342 (2) | C26—C26i | 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) |
C6i—C6—C2 | 126.33 (15) | C26i—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
top
Crystal data top
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) Å3 | T = 293 K |
Z = 4 | Octahedral, red-brown |
F(000) = 528 | 0.3 × 0.3 × 0.3 mm |
Data collection top
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 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.3816P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C6i | 1.333 (4) | C26—C26i | 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) |
C6i—C6—C2 | 127.0 (2) | C26i—C26—C22 | 128 (3) |
C3—O8—C9 | 117.48 (18) | C23—O28—C29 | 118 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |