In the crystal structure of the title compound, C
18H
10N
2S
3, the terminal thiophene rings are disordered. This disorder is of a flip-type and has been observed in some other thiophene derivatives. The molecule as a whole is approximately planar; the dihedral angle between the terminal five-membered rings is 6.0 (2)°. The crystal packing is determined by van der Waals interactions, π–π stair-like stacking between the thiophene rings, and some weak C—H
S and C—H
π short directional contacts.
Supporting information
CCDC reference: 629655
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.041
- wR factor = 0.095
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C55
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C56
PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C25 - C26 ... 1.35 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C55 - C56 ... 1.35 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C22 - C22A ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C52 - C52A ... 1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24 .. S27 .. 2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25 .. S57 .. 3.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27 .. S24 .. 3.05 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H57 .. S57 .. 3.00 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.80 Deg.
S57 -C56 -C57 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97.
2,5-bis(2-cyano-2-thienylvinyl)thiophene
top
Crystal data top
C18H10N2S3 | F(000) = 1440 |
Mr = 350.46 | Dx = 1.456 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2112 reflections |
a = 12.379 (2) Å | θ = 3–22° |
b = 12.651 (2) Å | µ = 0.46 mm−1 |
c = 20.421 (4) Å | T = 153 K |
V = 3198.1 (10) Å3 | Block, colourless |
Z = 8 | 0.3 × 0.1 × 0.1 mm |
Data collection top
Bruker P4 CCD diffractometer | 2672 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.4°, θmin = 2.0° |
ω scans | h = −15→14 |
17718 measured reflections | k = −14→15 |
3269 independent reflections | l = −25→19 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0326P)2 + 2.6519P] where P = (Fo2 + 2Fc2)/3 |
3269 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.21 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 | Occ. (<1) |
S1 | 0.24314 (4) | 0.87797 (4) | 0.62424 (2) | 0.02180 (14) | |
C2 | 0.14951 (16) | 0.96188 (16) | 0.66012 (10) | 0.0231 (4) | |
C21 | 0.17351 (17) | 1.05315 (16) | 0.69922 (10) | 0.0229 (4) | |
H21 | 0.1121 | 1.0871 | 0.7175 | 0.027* | |
C22 | 0.26953 (15) | 1.09897 (15) | 0.71441 (9) | 0.0204 (4) | |
C22A | 0.37042 (17) | 1.05793 (16) | 0.69020 (10) | 0.0251 (4) | |
N22A | 0.45350 (15) | 1.02981 (16) | 0.67211 (10) | 0.0373 (5) | |
C23 | 0.28066 (16) | 1.19331 (15) | 0.75542 (10) | 0.0211 (4) | |
S24 | 0.16941 (5) | 1.26442 (8) | 0.78224 (5) | 0.0221 (2) | 0.81 |
C24 | 0.1972 (15) | 1.2522 (17) | 0.7831 (10) | 0.0221 (2) | 0.19 |
H24 | 0.1223 | 1.2372 | 0.7796 | 0.027* | 0.19 |
C25 | 0.25055 (18) | 1.35106 (18) | 0.82234 (10) | 0.0287 (5) | |
H25 | 0.2231 | 1.4085 | 0.8473 | 0.034* | |
C26 | 0.35722 (17) | 1.33179 (17) | 0.81597 (11) | 0.0304 (5) | |
H26 | 0.4134 | 1.3727 | 0.8349 | 0.036* | |
C27 | 0.3722 (5) | 1.2402 (9) | 0.7763 (6) | 0.0351 (13) | 0.81 |
H27 | 0.4418 | 1.2141 | 0.7652 | 0.042* | 0.81 |
S27 | 0.4049 (6) | 1.2339 (10) | 0.7789 (7) | 0.0351 (13) | 0.19 |
C3 | 0.04503 (17) | 0.92962 (17) | 0.64652 (10) | 0.0270 (5) | |
H3 | −0.0173 | 0.9656 | 0.6620 | 0.032* | |
C4 | 0.04070 (17) | 0.83874 (17) | 0.60774 (10) | 0.0265 (5) | |
H4 | −0.0250 | 0.8069 | 0.5940 | 0.032* | |
C5 | 0.14155 (16) | 0.79979 (16) | 0.59135 (10) | 0.0237 (4) | |
C51 | 0.15683 (17) | 0.70677 (16) | 0.55207 (10) | 0.0238 (4) | |
H51 | 0.0919 | 0.6743 | 0.5375 | 0.029* | |
C52 | 0.24838 (17) | 0.65775 (16) | 0.53237 (10) | 0.0241 (4) | |
C52A | 0.35359 (18) | 0.69688 (17) | 0.55006 (11) | 0.0284 (5) | |
N52A | 0.43930 (17) | 0.72573 (17) | 0.56234 (11) | 0.0416 (5) | |
C53 | 0.24861 (18) | 0.56204 (16) | 0.49205 (10) | 0.0257 (4) | |
S54 | 0.1372 (2) | 0.5072 (2) | 0.46177 (16) | 0.0266 (3) | 0.64 |
C54 | 0.1514 (19) | 0.517 (2) | 0.4626 (12) | 0.0266 (3) | 0.36 |
H54 | 0.0795 | 0.5436 | 0.4637 | 0.032* | 0.36 |
C55 | 0.1984 (3) | 0.4123 (2) | 0.42548 (12) | 0.0508 (8) | |
H55 | 0.1613 | 0.3612 | 0.3998 | 0.061* | |
C56 | 0.3062 (3) | 0.4102 (2) | 0.43404 (13) | 0.0509 (8) | |
H56 | 0.3535 | 0.3580 | 0.4169 | 0.061* | |
C57 | 0.3415 (12) | 0.5068 (9) | 0.4765 (7) | 0.0239 (6) | 0.64 |
H57 | 0.4131 | 0.5244 | 0.4892 | 0.029* | 0.64 |
S57 | 0.3530 (5) | 0.4887 (3) | 0.4727 (3) | 0.0239 (6) | 0.36 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0215 (3) | 0.0215 (3) | 0.0224 (3) | 0.0001 (2) | −0.00059 (19) | −0.00041 (19) |
C2 | 0.0230 (10) | 0.0239 (10) | 0.0223 (10) | 0.0003 (8) | 0.0013 (8) | 0.0006 (8) |
C21 | 0.0219 (10) | 0.0239 (10) | 0.0228 (10) | 0.0004 (8) | 0.0037 (8) | −0.0011 (8) |
C22 | 0.0210 (10) | 0.0210 (9) | 0.0191 (10) | 0.0035 (8) | 0.0011 (7) | 0.0028 (8) |
C22A | 0.0247 (11) | 0.0217 (10) | 0.0290 (11) | 0.0017 (8) | −0.0034 (9) | −0.0013 (9) |
N22A | 0.0244 (10) | 0.0349 (11) | 0.0527 (13) | 0.0074 (8) | −0.0005 (9) | −0.0094 (10) |
C23 | 0.0192 (10) | 0.0224 (10) | 0.0218 (10) | 0.0010 (8) | 0.0018 (8) | 0.0014 (8) |
S24 | 0.0174 (5) | 0.0250 (4) | 0.0240 (3) | 0.0020 (3) | 0.0021 (3) | −0.0040 (3) |
C24 | 0.0174 (5) | 0.0250 (4) | 0.0240 (3) | 0.0020 (3) | 0.0021 (3) | −0.0040 (3) |
C25 | 0.0280 (11) | 0.0327 (12) | 0.0255 (11) | 0.0009 (9) | 0.0024 (9) | −0.0049 (9) |
C26 | 0.0248 (11) | 0.0250 (11) | 0.0412 (13) | −0.0056 (9) | 0.0009 (9) | −0.0044 (10) |
C27 | 0.032 (4) | 0.0325 (14) | 0.0408 (13) | −0.008 (3) | 0.008 (3) | −0.0038 (10) |
S27 | 0.032 (4) | 0.0325 (14) | 0.0408 (13) | −0.008 (3) | 0.008 (3) | −0.0038 (10) |
C3 | 0.0219 (10) | 0.0315 (12) | 0.0275 (11) | −0.0006 (9) | 0.0021 (8) | −0.0040 (9) |
C4 | 0.0239 (10) | 0.0298 (11) | 0.0259 (11) | −0.0044 (9) | −0.0009 (8) | −0.0018 (9) |
C5 | 0.0255 (11) | 0.0241 (10) | 0.0214 (10) | −0.0014 (8) | −0.0015 (8) | 0.0012 (8) |
C51 | 0.0260 (11) | 0.0243 (10) | 0.0213 (10) | −0.0031 (9) | −0.0016 (8) | 0.0018 (8) |
C52 | 0.0279 (10) | 0.0233 (10) | 0.0209 (10) | −0.0030 (9) | 0.0001 (8) | 0.0038 (8) |
C52A | 0.0310 (13) | 0.0261 (11) | 0.0281 (11) | −0.0014 (9) | 0.0052 (9) | −0.0048 (9) |
N52A | 0.0320 (12) | 0.0401 (12) | 0.0527 (13) | −0.0031 (9) | 0.0050 (10) | −0.0134 (10) |
C53 | 0.0335 (11) | 0.0214 (10) | 0.0222 (10) | −0.0014 (9) | 0.0043 (9) | 0.0031 (8) |
S54 | 0.0222 (10) | 0.0289 (9) | 0.0287 (4) | −0.0078 (5) | 0.0018 (6) | −0.0067 (5) |
C54 | 0.0222 (10) | 0.0289 (9) | 0.0287 (4) | −0.0078 (5) | 0.0018 (6) | −0.0067 (5) |
C55 | 0.093 (2) | 0.0341 (14) | 0.0258 (13) | −0.0327 (15) | 0.0068 (14) | −0.0064 (11) |
C56 | 0.082 (2) | 0.0347 (14) | 0.0361 (15) | 0.0251 (15) | 0.0242 (14) | 0.0101 (12) |
C57 | 0.0245 (15) | 0.0224 (18) | 0.0249 (9) | 0.0054 (11) | 0.0012 (8) | −0.0020 (11) |
S57 | 0.0245 (15) | 0.0224 (18) | 0.0249 (9) | 0.0054 (11) | 0.0012 (8) | −0.0020 (11) |
Geometric parameters (Å, º) top
S1—C2 | 1.734 (2) | C3—H3 | 0.9500 |
S1—C5 | 1.735 (2) | C4—C5 | 1.383 (3) |
C2—C3 | 1.384 (3) | C4—H4 | 0.9500 |
C2—C21 | 1.435 (3) | C5—C51 | 1.437 (3) |
C21—C22 | 1.358 (3) | C51—C52 | 1.353 (3) |
C21—H21 | 0.9500 | C51—H51 | 0.9500 |
C22—C22A | 1.440 (3) | C52—C52A | 1.439 (3) |
C22—C23 | 1.465 (3) | C52—C53 | 1.464 (3) |
C22A—N22A | 1.149 (3) | C52A—N52A | 1.150 (3) |
C23—C27 | 1.348 (9) | C53—C57 | 1.383 (12) |
C23—C24 | 1.393 (18) | C53—C54 | 1.46 (2) |
C23—S27 | 1.691 (9) | C53—S57 | 1.640 (4) |
C23—S24 | 1.734 (2) | C53—S54 | 1.663 (3) |
S24—C25 | 1.697 (2) | S54—C55 | 1.602 (5) |
C24—C25 | 1.63 (2) | C54—C55 | 1.64 (3) |
C24—H24 | 0.9500 | C54—H54 | 0.9500 |
C25—C26 | 1.349 (3) | C55—C56 | 1.346 (4) |
C25—H25 | 0.9500 | C55—H55 | 0.9500 |
C26—C27 | 1.427 (12) | C56—S57 | 1.395 (7) |
C26—S27 | 1.567 (12) | C56—C57 | 1.561 (14) |
C26—H26 | 0.9500 | C56—H56 | 0.9500 |
C27—H27 | 0.9500 | C57—H57 | 0.9500 |
C3—C4 | 1.397 (3) | | |
| | | |
C2—S1—C5 | 91.61 (10) | C5—C4—C3 | 113.31 (19) |
C3—C2—C21 | 122.84 (19) | C5—C4—H4 | 123.3 |
C3—C2—S1 | 111.05 (15) | C3—C4—H4 | 123.3 |
C21—C2—S1 | 126.11 (16) | C4—C5—C51 | 123.08 (19) |
C22—C21—C2 | 130.66 (19) | C4—C5—S1 | 110.94 (15) |
C22—C21—H21 | 114.7 | C51—C5—S1 | 125.98 (16) |
C2—C21—H21 | 114.7 | C52—C51—C5 | 130.7 (2) |
C21—C22—C22A | 121.78 (18) | C52—C51—H51 | 114.7 |
C21—C22—C23 | 124.10 (18) | C5—C51—H51 | 114.7 |
C22A—C22—C23 | 114.11 (17) | C51—C52—C52A | 121.71 (19) |
N22A—C22A—C22 | 176.4 (2) | C51—C52—C53 | 123.2 (2) |
C27—C23—C22 | 128.2 (5) | C52A—C52—C53 | 115.07 (19) |
C24—C23—C22 | 126.7 (9) | N52A—C52A—C52 | 177.4 (2) |
C24—C23—S27 | 113.4 (10) | C57—C53—C52 | 123.3 (7) |
C22—C23—S27 | 119.7 (4) | C52—C53—C54 | 123.4 (11) |
C27—C23—S24 | 109.9 (5) | C52—C53—S57 | 127.2 (3) |
C22—C23—S24 | 121.92 (15) | C54—C53—S57 | 109.4 (12) |
S27—C23—S24 | 118.4 (4) | C57—C53—S54 | 113.2 (7) |
C25—S24—C23 | 91.00 (11) | C52—C53—S54 | 123.5 (2) |
C23—C24—C25 | 108.1 (12) | S57—C53—S54 | 109.2 (3) |
C23—C24—H24 | 125.9 | C55—S54—C53 | 95.3 (2) |
C25—C24—H24 | 125.9 | C53—C54—C55 | 102.3 (16) |
C26—C25—C24 | 102.2 (6) | C53—C54—H54 | 128.8 |
C26—C25—S24 | 114.59 (17) | C55—C54—H54 | 128.9 |
C26—C25—H25 | 122.7 | C56—C55—S54 | 115.0 (2) |
C24—C25—H25 | 135.0 | C56—C55—C54 | 108.0 (8) |
S24—C25—H25 | 122.7 | C56—C55—H55 | 122.5 |
C25—C26—C27 | 109.2 (3) | S54—C55—H55 | 122.5 |
C25—C26—S27 | 123.9 (4) | C54—C55—H55 | 129.5 |
C25—C26—H26 | 125.4 | C55—C56—S57 | 118.1 (3) |
C27—C26—H26 | 125.4 | C55—C56—C57 | 109.5 (5) |
S27—C26—H26 | 110.6 | S57—C56—C57 | 8.8 (7) |
C23—C27—C26 | 115.3 (5) | C55—C56—H56 | 125.2 |
C23—C27—H27 | 122.3 | S57—C56—H56 | 116.6 |
C26—C27—H27 | 122.3 | C57—C56—H56 | 125.2 |
C26—S27—C23 | 92.0 (4) | C53—C57—C56 | 106.9 (11) |
C2—C3—C4 | 113.09 (19) | C53—C57—H57 | 126.6 |
C2—C3—H3 | 123.5 | C56—C57—H57 | 126.6 |
C4—C3—H3 | 123.5 | C56—S57—C53 | 102.2 (4) |
| | | |
C5—S1—C2—C3 | −0.15 (17) | C3—C4—C5—C51 | 179.69 (19) |
C5—S1—C2—C21 | 179.64 (19) | C3—C4—C5—S1 | −0.4 (2) |
C3—C2—C21—C22 | −176.0 (2) | C2—S1—C5—C4 | 0.32 (17) |
S1—C2—C21—C22 | 4.2 (3) | C2—S1—C5—C51 | −179.79 (19) |
C2—C21—C22—C22A | 0.6 (3) | C4—C5—C51—C52 | −179.1 (2) |
C2—C21—C22—C23 | 179.9 (2) | S1—C5—C51—C52 | 1.0 (3) |
C21—C22—C23—C27 | 175.6 (6) | C5—C51—C52—C52A | −0.1 (3) |
C22A—C22—C23—C27 | −5.1 (7) | C5—C51—C52—C53 | 179.8 (2) |
C21—C22—C23—C24 | −2.3 (11) | C51—C52—C53—C57 | −174.4 (7) |
C22A—C22—C23—C24 | 177.1 (11) | C52A—C52—C53—C57 | 5.6 (7) |
C21—C22—C23—S27 | 172.2 (5) | C51—C52—C53—C54 | 7.7 (12) |
C22A—C22—C23—S27 | −8.4 (6) | C52A—C52—C53—C54 | −172.4 (12) |
C21—C22—C23—S24 | −6.7 (3) | C51—C52—C53—S57 | −172.3 (3) |
C22A—C22—C23—S24 | 172.69 (15) | C52A—C52—C53—S57 | 7.7 (4) |
C27—C23—S24—C25 | −1.9 (5) | C51—C52—C53—S54 | 4.2 (3) |
C22—C23—S24—C25 | 180.00 (17) | C52A—C52—C53—S54 | −175.9 (2) |
C22—C23—C24—C25 | −178.3 (4) | C57—C53—S54—C55 | −1.4 (7) |
S27—C23—C24—C25 | 7.0 (15) | C52—C53—S54—C55 | 179.87 (19) |
C23—C24—C25—C26 | −4.2 (13) | C52—C53—C54—C55 | −178.8 (5) |
C23—S24—C25—C26 | 1.3 (2) | S57—C53—C54—C55 | 1.2 (15) |
S24—C25—C26—C27 | −0.4 (5) | C53—S54—C55—C56 | 2.0 (3) |
C24—C25—C26—S27 | −0.5 (10) | C53—C54—C55—C56 | −2.5 (15) |
C22—C23—C27—C26 | −180.0 (4) | C54—C55—C56—S57 | 3.0 (10) |
S24—C23—C27—C26 | 2.1 (9) | S54—C55—C56—C57 | −2.0 (6) |
C25—C26—C27—C23 | −1.1 (9) | C52—C53—C57—C56 | 179.2 (4) |
C25—C26—S27—C23 | 3.9 (8) | C54—C53—C57—C56 | −2.7 (14) |
C24—C23—S27—C26 | −6.4 (12) | S54—C53—C57—C56 | 0.5 (10) |
C22—C23—S27—C26 | 178.4 (3) | C55—C56—C57—C53 | 0.9 (10) |
C21—C2—C3—C4 | −179.85 (19) | C55—C56—S57—C53 | −2.2 (5) |
S1—C2—C3—C4 | −0.1 (2) | C52—C53—S57—C56 | −179.8 (2) |
C2—C3—C4—C5 | 0.3 (3) | C54—C53—S57—C56 | 0.3 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···S27i | 0.95 | 2.94 | 3.84 (2) | 158 |
C25—H25···S57ii | 0.95 | 3.02 | 3.896 (6) | 153 |
C27—H27···S24iii | 0.95 | 3.05 | 3.880 (8) | 147 |
C55—H55···S24iv | 0.95 | 2.88 | 3.699 (3) | 145 |
C57—H57···S57v | 0.95 | 3.00 | 3.921 (10) | 163 |
C25—H25···Cg3ii | 0.95 | 2.69 | 3.502 (2) | 144 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+1/2, −y+2, z+1/2; (iii) x+1/2, y, −z+3/2; (iv) x, −y+3/2, z−1/2; (v) −x+1, −y+1, −z+1. |