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The cyclo­pentene ring of the title compound, C15H14Cl2S2, is almost planar. The two thio­phene rings are twisted out of the mean plane of the cyclo­pentene ring by 39.97 (5) and 50.84 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042929/hb2173sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042929/hb2173Isup2.hkl
Contains datablock I

CCDC reference: 629828

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.070
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

1,2-Bis(5-chloro-2-methyl-3-thienyl)cyclopentene top
Crystal data top
C15H14Cl2S2F(000) = 680
Mr = 329.28Dx = 1.457 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8245 reflections
a = 8.7555 (12) Åθ = 3.8–28.6°
b = 12.2720 (14) ŵ = 0.69 mm1
c = 14.256 (2) ÅT = 173 K
β = 101.513 (12)°Block, colourless
V = 1501.0 (3) Å30.45 × 0.38 × 0.36 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
3724 independent reflections
Radiation source: fine-focus sealed tube2750 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 28.7°, θmin = 3.8°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1111
Tmin = 0.746, Tmax = 0.788k = 1616
7653 measured reflectionsl = 1119
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0444P)2]
where P = (Fo2 + 2Fc2)/3
3724 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (250 MHz, CDCl3, δ, p.p.m.): 1.88 (s, 6H), 2.02 (m, 2H), 2.71 (t, 4H, J = 7.5 Hz), 6.57 (s, 1H); 13C NMR (63 MHz, CDCl3, δ, p.p.m.): 14.1, 22.8, 38.3, 125.2, 126.7, 133.3, 134.5, 134.8.

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*/Ueq
C10.52964 (16)0.57902 (11)0.35089 (11)0.0295 (3)
C20.52121 (16)0.67692 (11)0.39255 (11)0.0294 (3)
C30.37252 (17)0.68862 (12)0.43006 (13)0.0363 (3)
H3A0.31420.75450.40360.044*
H3B0.39480.69300.50080.044*
C40.2809 (2)0.58512 (14)0.39545 (18)0.0525 (5)
H4A0.24010.55140.44850.063*
H4B0.19190.60260.34300.063*
C50.39302 (18)0.50723 (12)0.35985 (13)0.0377 (3)
H5A0.42570.44760.40630.045*
H5B0.34450.47530.29720.045*
C110.64985 (16)0.53835 (10)0.30143 (11)0.0290 (3)
C120.71820 (17)0.43207 (11)0.32065 (11)0.0325 (3)
H120.69010.38240.36540.039*
C130.82660 (17)0.41101 (12)0.26801 (12)0.0345 (3)
Cl130.93681 (5)0.29482 (3)0.27187 (4)0.04898 (12)
S140.84686 (5)0.51597 (3)0.19105 (3)0.03666 (9)
C150.70666 (16)0.59240 (11)0.23157 (11)0.0305 (3)
C160.66349 (18)0.70266 (12)0.18864 (12)0.0360 (3)
H16A0.55830.72180.19690.054*
H16B0.66610.70110.12020.054*
H16C0.73790.75710.22080.054*
C210.63624 (16)0.76555 (11)0.40757 (10)0.0291 (3)
C220.58983 (18)0.87799 (11)0.39537 (12)0.0344 (3)
H220.48480.90120.37590.041*
C230.71239 (19)0.94661 (12)0.41473 (13)0.0383 (3)
Cl230.70870 (6)1.08626 (3)0.40665 (5)0.06566 (17)
S240.88643 (4)0.88025 (3)0.44916 (3)0.03688 (10)
C250.79449 (17)0.75478 (11)0.43789 (11)0.0315 (3)
C260.89306 (17)0.65358 (13)0.46486 (13)0.0399 (4)
H26A0.83140.59820.49010.060*
H26B0.98480.67220.51380.060*
H26C0.92670.62500.40810.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0294 (6)0.0313 (6)0.0288 (7)0.0003 (5)0.0082 (6)0.0037 (5)
C20.0276 (6)0.0330 (6)0.0282 (7)0.0022 (5)0.0068 (5)0.0033 (5)
C30.0321 (7)0.0396 (7)0.0401 (9)0.0050 (5)0.0143 (7)0.0033 (6)
C40.0397 (9)0.0454 (9)0.0788 (15)0.0040 (7)0.0275 (9)0.0007 (9)
C50.0347 (7)0.0342 (7)0.0476 (9)0.0036 (5)0.0163 (7)0.0024 (6)
C110.0293 (6)0.0303 (6)0.0281 (7)0.0013 (5)0.0076 (5)0.0012 (5)
C120.0350 (7)0.0329 (6)0.0309 (8)0.0011 (5)0.0098 (6)0.0012 (5)
C130.0346 (7)0.0369 (7)0.0325 (8)0.0041 (5)0.0077 (6)0.0020 (6)
Cl130.0505 (2)0.0490 (2)0.0484 (3)0.01877 (17)0.01241 (19)0.00181 (18)
S140.03619 (19)0.04417 (19)0.03302 (19)0.00126 (14)0.01509 (15)0.00018 (15)
C150.0299 (6)0.0336 (6)0.0288 (7)0.0023 (5)0.0078 (6)0.0010 (5)
C160.0403 (8)0.0370 (7)0.0323 (8)0.0016 (6)0.0111 (6)0.0050 (6)
C210.0304 (7)0.0328 (6)0.0244 (6)0.0019 (5)0.0067 (5)0.0017 (5)
C220.0352 (7)0.0328 (6)0.0337 (8)0.0032 (5)0.0030 (6)0.0018 (6)
C230.0407 (8)0.0322 (6)0.0395 (9)0.0000 (6)0.0019 (7)0.0037 (6)
Cl230.0612 (3)0.03293 (19)0.0907 (4)0.00307 (17)0.0140 (3)0.0025 (2)
S240.03210 (18)0.03865 (18)0.0385 (2)0.00359 (13)0.00378 (15)0.00760 (15)
C250.0312 (7)0.0356 (7)0.0282 (7)0.0008 (5)0.0067 (6)0.0044 (5)
C260.0300 (7)0.0420 (7)0.0433 (10)0.0053 (6)0.0028 (7)0.0076 (7)
Geometric parameters (Å, º) top
C1—C21.349 (2)C13—S141.7239 (16)
C1—C111.466 (2)S14—C151.7329 (15)
C1—C51.5113 (19)C15—C161.5021 (19)
C2—C211.4688 (19)C16—H16A0.9800
C2—C31.510 (2)C16—H16B0.9800
C3—C41.530 (2)C16—H16C0.9800
C3—H3A0.9900C21—C251.373 (2)
C3—H3B0.9900C21—C221.4391 (19)
C4—C51.527 (2)C22—C231.349 (2)
C4—H4A0.9900C22—H220.9500
C4—H4B0.9900C23—S241.7111 (16)
C5—H5A0.9900C23—Cl231.7175 (15)
C5—H5B0.9900S24—C251.7301 (15)
C11—C151.370 (2)C25—C261.517 (2)
C11—C121.4384 (18)C26—H26A0.9800
C12—C131.347 (2)C26—H26B0.9800
C12—H120.9500C26—H26C0.9800
C13—Cl131.7165 (15)
C2—C1—C11128.50 (13)C12—C13—S14112.62 (11)
C2—C1—C5111.61 (13)Cl13—C13—S14120.83 (10)
C11—C1—C5119.89 (12)C13—S14—C1591.29 (7)
C1—C2—C21128.88 (13)C11—C15—C16129.35 (13)
C1—C2—C3111.56 (12)C11—C15—S14111.37 (10)
C21—C2—C3119.51 (12)C16—C15—S14119.28 (11)
C2—C3—C4103.90 (13)C15—C16—H16A109.5
C2—C3—H3A111.0C15—C16—H16B109.5
C4—C3—H3A111.0H16A—C16—H16B109.5
C2—C3—H3B111.0C15—C16—H16C109.5
C4—C3—H3B111.0H16A—C16—H16C109.5
H3A—C3—H3B109.0H16B—C16—H16C109.5
C5—C4—C3107.24 (13)C25—C21—C22111.92 (12)
C5—C4—H4A110.3C25—C21—C2126.45 (12)
C3—C4—H4A110.3C22—C21—C2121.57 (12)
C5—C4—H4B110.3C23—C22—C21112.34 (13)
C3—C4—H4B110.3C23—C22—H22123.8
H4A—C4—H4B108.5C21—C22—H22123.8
C1—C5—C4103.60 (12)C22—C23—S24112.84 (11)
C1—C5—H5A111.0C22—C23—Cl23127.29 (12)
C4—C5—H5A111.0S24—C23—Cl23119.86 (9)
C1—C5—H5B111.0C23—S24—C2591.47 (7)
C4—C5—H5B111.0C21—C25—C26130.23 (13)
H5A—C5—H5B109.0C21—C25—S24111.41 (10)
C15—C11—C12112.32 (13)C26—C25—S24118.32 (11)
C15—C11—C1125.76 (12)C25—C26—H26A109.5
C12—C11—C1121.89 (13)C25—C26—H26B109.5
C13—C12—C11112.36 (13)H26A—C26—H26B109.5
C13—C12—H12123.8C25—C26—H26C109.5
C11—C12—H12123.8H26A—C26—H26C109.5
C12—C13—Cl13126.55 (12)H26B—C26—H26C109.5
C11—C1—C2—C216.2 (3)C1—C11—C15—C160.0 (2)
C5—C1—C2—C21173.75 (14)C12—C11—C15—S141.53 (16)
C11—C1—C2—C3176.31 (14)C1—C11—C15—S14179.65 (11)
C5—C1—C2—C33.76 (18)C13—S14—C15—C110.49 (11)
C1—C2—C3—C45.63 (18)C13—S14—C15—C16179.20 (12)
C21—C2—C3—C4176.60 (14)C1—C2—C21—C2542.6 (2)
C2—C3—C4—C512.51 (19)C3—C2—C21—C25134.70 (16)
C2—C1—C5—C411.48 (19)C1—C2—C21—C22140.41 (16)
C11—C1—C5—C4168.58 (15)C3—C2—C21—C2242.2 (2)
C3—C4—C5—C114.5 (2)C25—C21—C22—C231.2 (2)
C2—C1—C11—C1549.2 (2)C2—C21—C22—C23178.51 (14)
C5—C1—C11—C15130.91 (16)C21—C22—C23—S240.60 (19)
C2—C1—C11—C12132.89 (16)C21—C22—C23—Cl23178.51 (13)
C5—C1—C11—C1247.0 (2)C22—C23—S24—C250.06 (14)
C15—C11—C12—C132.13 (18)Cl23—C23—S24—C25179.24 (12)
C1—C11—C12—C13179.67 (13)C22—C21—C25—C26176.34 (16)
C11—C12—C13—Cl13178.61 (11)C2—C21—C25—C260.9 (3)
C11—C12—C13—S141.75 (17)C22—C21—C25—S241.18 (17)
C12—C13—S14—C150.75 (12)C2—C21—C25—S24178.38 (12)
Cl13—C13—S14—C15179.58 (10)C23—S24—C25—C210.73 (13)
C12—C11—C15—C16178.11 (14)C23—S24—C25—C26177.12 (13)
 

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