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In the crystal structure of the title compound, C15H14Cl2S2, two substituted thio­phene rings are cis positioned with respect to the double bond of a cyclo­pentene ring. The ring skeleton of the mol­ecule is not planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006033/kp6041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006033/kp6041Isup2.hkl
Contains datablock I

CCDC reference: 258489

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.182
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H5A .. H8A .. 2.15 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,2-Bis(5-chloro-2-methyl-3-thienyl)cyclopentene top
Crystal data top
C15H14Cl2S2F(000) = 680
Mr = 329.28Dx = 1.423 Mg m3
Monoclinic, P21/cMelting point: 77 K
Hall symbol: -P2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.8423 (8) ÅCell parameters from 3518 reflections
b = 12.2784 (11) Åθ = 2.2–23.2°
c = 14.4380 (13) ŵ = 0.68 mm1
β = 101.374 (2)°T = 293 K
V = 1536.7 (2) Å3Block, colourless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
φ and ω scansh = 1111
12983 measured reflectionsk = 1515
3505 independent reflectionsl = 1818
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0971P)2 + 0.2616P]
where P = (Fo2 + 2Fc2)/3
3505 reflections(Δ/σ)max = 0.008
174 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.44 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*/Ueq
C10.2876 (4)0.9431 (3)0.0818 (2)0.0603 (8)
C20.4091 (4)0.8741 (3)0.1017 (2)0.0537 (7)
H20.51110.89670.11960.064*
C30.3620 (3)0.7616 (2)0.09171 (18)0.0447 (6)
C40.2052 (3)0.7518 (3)0.0609 (2)0.0487 (7)
C50.1037 (3)0.6469 (2)0.0341 (2)0.0501 (7)
H5A0.15530.59820.00140.075*
H5B0.00560.66730.00340.075*
H5C0.08820.61130.09070.075*
C60.4762 (3)0.6733 (2)0.10795 (19)0.0458 (7)
C70.6239 (3)0.6842 (3)0.0731 (2)0.0581 (8)
H7A0.68260.74630.10220.070*
H7B0.60380.69330.00510.070*
C80.7110 (4)0.5786 (3)0.1015 (3)0.0826 (12)
H8A0.73630.54340.04640.099*
H8B0.80600.59340.14610.099*
C90.6078 (4)0.5067 (3)0.1460 (3)0.0586 (8)
H9A0.65920.48400.20870.070*
H9B0.57800.44240.10770.070*
C100.4686 (3)0.5763 (2)0.15092 (18)0.0444 (6)
C110.3480 (3)0.5356 (2)0.19963 (18)0.0445 (6)
C120.2806 (3)0.4301 (2)0.1808 (2)0.0519 (7)
H120.30850.38160.13760.062*
C130.1730 (4)0.4082 (3)0.2321 (2)0.0556 (8)
C140.2909 (3)0.5900 (2)0.26791 (19)0.0485 (7)
C150.3344 (4)0.6998 (3)0.3104 (2)0.0574 (8)
H15A0.44050.71450.30900.086*
H15B0.32010.70070.37460.086*
H15C0.27030.75450.27480.086*
Cl10.29323 (15)1.08227 (9)0.08708 (10)0.1098 (5)
Cl20.06406 (12)0.29260 (9)0.22798 (7)0.0857 (4)
S10.11573 (9)0.87732 (7)0.04753 (6)0.0606 (3)
S20.15228 (10)0.51325 (8)0.30735 (6)0.0614 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (2)0.0497 (19)0.0590 (19)0.0014 (15)0.0033 (15)0.0062 (14)
C20.0552 (17)0.0513 (18)0.0526 (17)0.0033 (14)0.0055 (13)0.0050 (13)
C30.0492 (15)0.0485 (16)0.0366 (13)0.0032 (12)0.0093 (11)0.0027 (11)
C40.0504 (16)0.0525 (17)0.0437 (15)0.0010 (13)0.0105 (12)0.0061 (13)
C50.0367 (14)0.0512 (17)0.0568 (17)0.0048 (12)0.0043 (12)0.0104 (13)
C60.0467 (15)0.0514 (17)0.0404 (14)0.0058 (12)0.0113 (11)0.0042 (12)
C70.0517 (17)0.062 (2)0.065 (2)0.0069 (14)0.0237 (15)0.0046 (15)
C80.066 (2)0.074 (3)0.120 (3)0.0047 (19)0.047 (2)0.005 (2)
C90.0568 (18)0.0547 (19)0.068 (2)0.0056 (14)0.0219 (15)0.0019 (15)
C100.0460 (15)0.0455 (16)0.0431 (14)0.0021 (12)0.0121 (11)0.0037 (12)
C110.0453 (15)0.0475 (16)0.0418 (14)0.0032 (12)0.0110 (11)0.0038 (12)
C120.0602 (18)0.0491 (17)0.0483 (16)0.0015 (14)0.0152 (13)0.0001 (13)
C130.0562 (17)0.0565 (19)0.0536 (17)0.0076 (14)0.0097 (14)0.0055 (14)
C140.0485 (16)0.0558 (18)0.0425 (14)0.0035 (13)0.0125 (12)0.0038 (13)
C150.0633 (19)0.0551 (19)0.0576 (18)0.0056 (15)0.0212 (15)0.0064 (14)
Cl10.1145 (9)0.0567 (7)0.1414 (11)0.0060 (6)0.0154 (8)0.0051 (6)
Cl20.0900 (7)0.0828 (7)0.0850 (7)0.0357 (5)0.0189 (5)0.0068 (5)
S10.0547 (5)0.0616 (5)0.0632 (5)0.0075 (4)0.0059 (4)0.0120 (4)
S20.0603 (5)0.0742 (6)0.0551 (5)0.0037 (4)0.0248 (4)0.0023 (4)
Geometric parameters (Å, º) top
C1—C21.354 (5)C8—H8A0.9700
C1—S11.706 (3)C8—H8B0.9700
C1—Cl11.711 (4)C9—C101.512 (4)
C2—C31.442 (4)C9—H9A0.9700
C2—H20.9300C9—H9B0.9700
C3—C41.375 (4)C10—C111.475 (4)
C3—C61.469 (4)C11—C141.367 (4)
C4—C51.574 (4)C11—C121.430 (4)
C4—S11.726 (3)C12—C131.343 (4)
C5—H5A0.9600C12—H120.9300
C5—H5B0.9600C13—Cl21.710 (3)
C5—H5C0.9600C13—S21.720 (3)
C6—C101.351 (4)C14—C151.499 (4)
C6—C71.495 (4)C14—S21.729 (3)
C7—C81.522 (5)C15—H15A0.9600
C7—H7A0.9700C15—H15B0.9600
C7—H7B0.9700C15—H15C0.9600
C8—C91.502 (5)
C2—C1—S1113.0 (3)C7—C8—H8B110.2
C2—C1—Cl1126.9 (3)H8A—C8—H8B108.5
S1—C1—Cl1120.2 (2)C8—C9—C10104.9 (3)
C1—C2—C3112.1 (3)C8—C9—H9A110.8
C1—C2—H2124.0C10—C9—H9A110.8
C3—C2—H2124.0C8—C9—H9B110.8
C4—C3—C2111.7 (3)C10—C9—H9B110.8
C4—C3—C6127.2 (3)H9A—C9—H9B108.9
C2—C3—C6121.0 (3)C6—C10—C11128.6 (3)
C3—C4—C5129.9 (3)C6—C10—C9111.2 (2)
C3—C4—S1111.6 (2)C11—C10—C9120.2 (3)
C5—C4—S1118.4 (2)C14—C11—C12112.4 (3)
C4—C5—H5A109.5C14—C11—C10125.6 (3)
C4—C5—H5B109.5C12—C11—C10122.0 (3)
H5A—C5—H5B109.5C13—C12—C11113.0 (3)
C4—C5—H5C109.5C13—C12—H12123.5
H5A—C5—H5C109.5C11—C12—H12123.5
H5B—C5—H5C109.5C12—C13—Cl2127.1 (3)
C10—C6—C3129.0 (3)C12—C13—S2111.9 (2)
C10—C6—C7111.0 (3)Cl2—C13—S2121.01 (19)
C3—C6—C7120.0 (3)C11—C14—C15129.3 (3)
C6—C7—C8105.2 (3)C11—C14—S2110.9 (2)
C6—C7—H7A110.7C15—C14—S2119.8 (2)
C8—C7—H7A110.7C14—C15—H15A109.5
C6—C7—H7B110.7C14—C15—H15B109.5
C8—C7—H7B110.7H15A—C15—H15B109.5
H7A—C7—H7B108.8C14—C15—H15C109.5
C9—C8—C7107.4 (3)H15A—C15—H15C109.5
C9—C8—H8A110.2H15B—C15—H15C109.5
C7—C8—H8A110.2C1—S1—C491.59 (15)
C9—C8—H8B110.2C13—S2—C1491.73 (14)
S1—C1—C2—C31.9 (4)C8—C9—C10—C11174.0 (3)
Cl1—C1—C2—C3178.8 (2)C6—C10—C11—C1450.5 (4)
C1—C2—C3—C42.4 (4)C9—C10—C11—C14128.5 (3)
C1—C2—C3—C6178.7 (3)C6—C10—C11—C12131.4 (3)
C2—C3—C4—C5175.8 (3)C9—C10—C11—C1249.6 (4)
C6—C3—C4—C50.3 (5)C14—C11—C12—C131.8 (4)
C2—C3—C4—S11.8 (3)C10—C11—C12—C13179.9 (3)
C6—C3—C4—S1177.8 (2)C11—C12—C13—Cl2178.5 (2)
C4—C3—C6—C1043.7 (5)C11—C12—C13—S21.5 (3)
C2—C3—C6—C10140.6 (3)C12—C11—C14—C15177.6 (3)
C4—C3—C6—C7135.1 (3)C10—C11—C14—C150.7 (5)
C2—C3—C6—C740.6 (4)C12—C11—C14—S21.2 (3)
C10—C6—C7—C80.5 (4)C10—C11—C14—S2179.4 (2)
C3—C6—C7—C8179.5 (3)C2—C1—S1—C40.8 (3)
C6—C7—C8—C93.7 (4)Cl1—C1—S1—C4179.9 (2)
C7—C8—C9—C105.2 (4)C3—C4—S1—C10.6 (2)
C3—C6—C10—C115.0 (5)C5—C4—S1—C1177.2 (2)
C7—C6—C10—C11176.1 (3)C12—C13—S2—C140.7 (3)
C3—C6—C10—C9176.0 (3)Cl2—C13—S2—C14179.3 (2)
C7—C6—C10—C92.9 (4)C11—C14—S2—C130.3 (2)
C8—C9—C10—C65.1 (4)C15—C14—S2—C13178.6 (2)
 

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