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In the crystal structure of the title compound, C18H10N2S3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050100/dn2097sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050100/dn2097Isup2.hkl
Contains datablock I

CCDC reference: 629655

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](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

Computing details top

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
C18H10N2S3F(000) = 1440
Mr = 350.46Dx = 1.456 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2112 reflections
a = 12.379 (2) Åθ = 3–22°
b = 12.651 (2) ŵ = 0.46 mm1
c = 20.421 (4) ÅT = 153 K
V = 3198.1 (10) Å3Block, colourless
Z = 80.3 × 0.1 × 0.1 mm
Data collection top
Bruker P4 CCD
diffractometer
2672 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 26.4°, θmin = 2.0°
ω scansh = 1514
17718 measured reflectionsk = 1415
3269 independent reflectionsl = 2519
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.36 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.24314 (4)0.87797 (4)0.62424 (2)0.02180 (14)
C20.14951 (16)0.96188 (16)0.66012 (10)0.0231 (4)
C210.17351 (17)1.05315 (16)0.69922 (10)0.0229 (4)
H210.11211.08710.71750.027*
C220.26953 (15)1.09897 (15)0.71441 (9)0.0204 (4)
C22A0.37042 (17)1.05793 (16)0.69020 (10)0.0251 (4)
N22A0.45350 (15)1.02981 (16)0.67211 (10)0.0373 (5)
C230.28066 (16)1.19331 (15)0.75542 (10)0.0211 (4)
S240.16941 (5)1.26442 (8)0.78224 (5)0.0221 (2)0.81
C240.1972 (15)1.2522 (17)0.7831 (10)0.0221 (2)0.19
H240.12231.23720.77960.027*0.19
C250.25055 (18)1.35106 (18)0.82234 (10)0.0287 (5)
H250.22311.40850.84730.034*
C260.35722 (17)1.33179 (17)0.81597 (11)0.0304 (5)
H260.41341.37270.83490.036*
C270.3722 (5)1.2402 (9)0.7763 (6)0.0351 (13)0.81
H270.44181.21410.76520.042*0.81
S270.4049 (6)1.2339 (10)0.7789 (7)0.0351 (13)0.19
C30.04503 (17)0.92962 (17)0.64652 (10)0.0270 (5)
H30.01730.96560.66200.032*
C40.04070 (17)0.83874 (17)0.60774 (10)0.0265 (5)
H40.02500.80690.59400.032*
C50.14155 (16)0.79979 (16)0.59135 (10)0.0237 (4)
C510.15683 (17)0.70677 (16)0.55207 (10)0.0238 (4)
H510.09190.67430.53750.029*
C520.24838 (17)0.65775 (16)0.53237 (10)0.0241 (4)
C52A0.35359 (18)0.69688 (17)0.55006 (11)0.0284 (5)
N52A0.43930 (17)0.72573 (17)0.56234 (11)0.0416 (5)
C530.24861 (18)0.56204 (16)0.49205 (10)0.0257 (4)
S540.1372 (2)0.5072 (2)0.46177 (16)0.0266 (3)0.64
C540.1514 (19)0.517 (2)0.4626 (12)0.0266 (3)0.36
H540.07950.54360.46370.032*0.36
C550.1984 (3)0.4123 (2)0.42548 (12)0.0508 (8)
H550.16130.36120.39980.061*
C560.3062 (3)0.4102 (2)0.43404 (13)0.0509 (8)
H560.35350.35800.41690.061*
C570.3415 (12)0.5068 (9)0.4765 (7)0.0239 (6)0.64
H570.41310.52440.48920.029*0.64
S570.3530 (5)0.4887 (3)0.4727 (3)0.0239 (6)0.36
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0215 (3)0.0215 (3)0.0224 (3)0.0001 (2)0.00059 (19)0.00041 (19)
C20.0230 (10)0.0239 (10)0.0223 (10)0.0003 (8)0.0013 (8)0.0006 (8)
C210.0219 (10)0.0239 (10)0.0228 (10)0.0004 (8)0.0037 (8)0.0011 (8)
C220.0210 (10)0.0210 (9)0.0191 (10)0.0035 (8)0.0011 (7)0.0028 (8)
C22A0.0247 (11)0.0217 (10)0.0290 (11)0.0017 (8)0.0034 (9)0.0013 (9)
N22A0.0244 (10)0.0349 (11)0.0527 (13)0.0074 (8)0.0005 (9)0.0094 (10)
C230.0192 (10)0.0224 (10)0.0218 (10)0.0010 (8)0.0018 (8)0.0014 (8)
S240.0174 (5)0.0250 (4)0.0240 (3)0.0020 (3)0.0021 (3)0.0040 (3)
C240.0174 (5)0.0250 (4)0.0240 (3)0.0020 (3)0.0021 (3)0.0040 (3)
C250.0280 (11)0.0327 (12)0.0255 (11)0.0009 (9)0.0024 (9)0.0049 (9)
C260.0248 (11)0.0250 (11)0.0412 (13)0.0056 (9)0.0009 (9)0.0044 (10)
C270.032 (4)0.0325 (14)0.0408 (13)0.008 (3)0.008 (3)0.0038 (10)
S270.032 (4)0.0325 (14)0.0408 (13)0.008 (3)0.008 (3)0.0038 (10)
C30.0219 (10)0.0315 (12)0.0275 (11)0.0006 (9)0.0021 (8)0.0040 (9)
C40.0239 (10)0.0298 (11)0.0259 (11)0.0044 (9)0.0009 (8)0.0018 (9)
C50.0255 (11)0.0241 (10)0.0214 (10)0.0014 (8)0.0015 (8)0.0012 (8)
C510.0260 (11)0.0243 (10)0.0213 (10)0.0031 (9)0.0016 (8)0.0018 (8)
C520.0279 (10)0.0233 (10)0.0209 (10)0.0030 (9)0.0001 (8)0.0038 (8)
C52A0.0310 (13)0.0261 (11)0.0281 (11)0.0014 (9)0.0052 (9)0.0048 (9)
N52A0.0320 (12)0.0401 (12)0.0527 (13)0.0031 (9)0.0050 (10)0.0134 (10)
C530.0335 (11)0.0214 (10)0.0222 (10)0.0014 (9)0.0043 (9)0.0031 (8)
S540.0222 (10)0.0289 (9)0.0287 (4)0.0078 (5)0.0018 (6)0.0067 (5)
C540.0222 (10)0.0289 (9)0.0287 (4)0.0078 (5)0.0018 (6)0.0067 (5)
C550.093 (2)0.0341 (14)0.0258 (13)0.0327 (15)0.0068 (14)0.0064 (11)
C560.082 (2)0.0347 (14)0.0361 (15)0.0251 (15)0.0242 (14)0.0101 (12)
C570.0245 (15)0.0224 (18)0.0249 (9)0.0054 (11)0.0012 (8)0.0020 (11)
S570.0245 (15)0.0224 (18)0.0249 (9)0.0054 (11)0.0012 (8)0.0020 (11)
Geometric parameters (Å, º) top
S1—C21.734 (2)C3—H30.9500
S1—C51.735 (2)C4—C51.383 (3)
C2—C31.384 (3)C4—H40.9500
C2—C211.435 (3)C5—C511.437 (3)
C21—C221.358 (3)C51—C521.353 (3)
C21—H210.9500C51—H510.9500
C22—C22A1.440 (3)C52—C52A1.439 (3)
C22—C231.465 (3)C52—C531.464 (3)
C22A—N22A1.149 (3)C52A—N52A1.150 (3)
C23—C271.348 (9)C53—C571.383 (12)
C23—C241.393 (18)C53—C541.46 (2)
C23—S271.691 (9)C53—S571.640 (4)
C23—S241.734 (2)C53—S541.663 (3)
S24—C251.697 (2)S54—C551.602 (5)
C24—C251.63 (2)C54—C551.64 (3)
C24—H240.9500C54—H540.9500
C25—C261.349 (3)C55—C561.346 (4)
C25—H250.9500C55—H550.9500
C26—C271.427 (12)C56—S571.395 (7)
C26—S271.567 (12)C56—C571.561 (14)
C26—H260.9500C56—H560.9500
C27—H270.9500C57—H570.9500
C3—C41.397 (3)
C2—S1—C591.61 (10)C5—C4—C3113.31 (19)
C3—C2—C21122.84 (19)C5—C4—H4123.3
C3—C2—S1111.05 (15)C3—C4—H4123.3
C21—C2—S1126.11 (16)C4—C5—C51123.08 (19)
C22—C21—C2130.66 (19)C4—C5—S1110.94 (15)
C22—C21—H21114.7C51—C5—S1125.98 (16)
C2—C21—H21114.7C52—C51—C5130.7 (2)
C21—C22—C22A121.78 (18)C52—C51—H51114.7
C21—C22—C23124.10 (18)C5—C51—H51114.7
C22A—C22—C23114.11 (17)C51—C52—C52A121.71 (19)
N22A—C22A—C22176.4 (2)C51—C52—C53123.2 (2)
C27—C23—C22128.2 (5)C52A—C52—C53115.07 (19)
C24—C23—C22126.7 (9)N52A—C52A—C52177.4 (2)
C24—C23—S27113.4 (10)C57—C53—C52123.3 (7)
C22—C23—S27119.7 (4)C52—C53—C54123.4 (11)
C27—C23—S24109.9 (5)C52—C53—S57127.2 (3)
C22—C23—S24121.92 (15)C54—C53—S57109.4 (12)
S27—C23—S24118.4 (4)C57—C53—S54113.2 (7)
C25—S24—C2391.00 (11)C52—C53—S54123.5 (2)
C23—C24—C25108.1 (12)S57—C53—S54109.2 (3)
C23—C24—H24125.9C55—S54—C5395.3 (2)
C25—C24—H24125.9C53—C54—C55102.3 (16)
C26—C25—C24102.2 (6)C53—C54—H54128.8
C26—C25—S24114.59 (17)C55—C54—H54128.9
C26—C25—H25122.7C56—C55—S54115.0 (2)
C24—C25—H25135.0C56—C55—C54108.0 (8)
S24—C25—H25122.7C56—C55—H55122.5
C25—C26—C27109.2 (3)S54—C55—H55122.5
C25—C26—S27123.9 (4)C54—C55—H55129.5
C25—C26—H26125.4C55—C56—S57118.1 (3)
C27—C26—H26125.4C55—C56—C57109.5 (5)
S27—C26—H26110.6S57—C56—C578.8 (7)
C23—C27—C26115.3 (5)C55—C56—H56125.2
C23—C27—H27122.3S57—C56—H56116.6
C26—C27—H27122.3C57—C56—H56125.2
C26—S27—C2392.0 (4)C53—C57—C56106.9 (11)
C2—C3—C4113.09 (19)C53—C57—H57126.6
C2—C3—H3123.5C56—C57—H57126.6
C4—C3—H3123.5C56—S57—C53102.2 (4)
C5—S1—C2—C30.15 (17)C3—C4—C5—C51179.69 (19)
C5—S1—C2—C21179.64 (19)C3—C4—C5—S10.4 (2)
C3—C2—C21—C22176.0 (2)C2—S1—C5—C40.32 (17)
S1—C2—C21—C224.2 (3)C2—S1—C5—C51179.79 (19)
C2—C21—C22—C22A0.6 (3)C4—C5—C51—C52179.1 (2)
C2—C21—C22—C23179.9 (2)S1—C5—C51—C521.0 (3)
C21—C22—C23—C27175.6 (6)C5—C51—C52—C52A0.1 (3)
C22A—C22—C23—C275.1 (7)C5—C51—C52—C53179.8 (2)
C21—C22—C23—C242.3 (11)C51—C52—C53—C57174.4 (7)
C22A—C22—C23—C24177.1 (11)C52A—C52—C53—C575.6 (7)
C21—C22—C23—S27172.2 (5)C51—C52—C53—C547.7 (12)
C22A—C22—C23—S278.4 (6)C52A—C52—C53—C54172.4 (12)
C21—C22—C23—S246.7 (3)C51—C52—C53—S57172.3 (3)
C22A—C22—C23—S24172.69 (15)C52A—C52—C53—S577.7 (4)
C27—C23—S24—C251.9 (5)C51—C52—C53—S544.2 (3)
C22—C23—S24—C25180.00 (17)C52A—C52—C53—S54175.9 (2)
C22—C23—C24—C25178.3 (4)C57—C53—S54—C551.4 (7)
S27—C23—C24—C257.0 (15)C52—C53—S54—C55179.87 (19)
C23—C24—C25—C264.2 (13)C52—C53—C54—C55178.8 (5)
C23—S24—C25—C261.3 (2)S57—C53—C54—C551.2 (15)
S24—C25—C26—C270.4 (5)C53—S54—C55—C562.0 (3)
C24—C25—C26—S270.5 (10)C53—C54—C55—C562.5 (15)
C22—C23—C27—C26180.0 (4)C54—C55—C56—S573.0 (10)
S24—C23—C27—C262.1 (9)S54—C55—C56—C572.0 (6)
C25—C26—C27—C231.1 (9)C52—C53—C57—C56179.2 (4)
C25—C26—S27—C233.9 (8)C54—C53—C57—C562.7 (14)
C24—C23—S27—C266.4 (12)S54—C53—C57—C560.5 (10)
C22—C23—S27—C26178.4 (3)C55—C56—C57—C530.9 (10)
C21—C2—C3—C4179.85 (19)C55—C56—S57—C532.2 (5)
S1—C2—C3—C40.1 (2)C52—C53—S57—C56179.8 (2)
C2—C3—C4—C50.3 (3)C54—C53—S57—C560.3 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24···S27i0.952.943.84 (2)158
C25—H25···S57ii0.953.023.896 (6)153
C27—H27···S24iii0.953.053.880 (8)147
C55—H55···S24iv0.952.883.699 (3)145
C57—H57···S57v0.953.003.921 (10)163
C25—H25···Cg3ii0.952.693.502 (2)144
Symmetry codes: (i) x1/2, 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, z1/2; (v) x+1, y+1, z+1.
 

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