1,2-Bis(5-chloro-2-methyl-3-thien­yl)cyclo­pentene

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)°.

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

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Computing details

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

Crystal data

C15H14Cl2S2	F(000) = 680
Mr = 329.28	Dx = 1.457 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8245 reflections
a = 8.7555 (12) Å	θ = 3.8–28.6°
b = 12.2720 (14) Å	µ = 0.69 mm^−1
c = 14.256 (2) Å	T = 173 K
β = 101.513 (12)°	Block, colourless
V = 1501.0 (3) Å^3	0.45 × 0.38 × 0.36 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 28.7°, θmin = 3.8°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −11→11
Tmin = 0.746, Tmax = 0.788	k = −16→16
7653 measured reflections	l = −11→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0444P)^2] where P = (Fo^2 + 2Fc^2)/3
3724 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.52964 (16)	0.57902 (11)	0.35089 (11)	0.0295 (3)
C2	0.52121 (16)	0.67692 (11)	0.39255 (11)	0.0294 (3)
C3	0.37252 (17)	0.68862 (12)	0.43006 (13)	0.0363 (3)
H3A	0.3142	0.7545	0.4036	0.044*
H3B	0.3948	0.6930	0.5008	0.044*
C4	0.2809 (2)	0.58512 (14)	0.39545 (18)	0.0525 (5)
H4A	0.2401	0.5514	0.4485	0.063*
H4B	0.1919	0.6026	0.3430	0.063*
C5	0.39302 (18)	0.50723 (12)	0.35985 (13)	0.0377 (3)
H5A	0.4257	0.4476	0.4063	0.045*
H5B	0.3445	0.4753	0.2972	0.045*
C11	0.64985 (16)	0.53835 (10)	0.30143 (11)	0.0290 (3)
C12	0.71820 (17)	0.43207 (11)	0.32065 (11)	0.0325 (3)
H12	0.6901	0.3824	0.3654	0.039*
C13	0.82660 (17)	0.41101 (12)	0.26801 (12)	0.0345 (3)
Cl13	0.93681 (5)	0.29482 (3)	0.27187 (4)	0.04898 (12)
S14	0.84686 (5)	0.51597 (3)	0.19105 (3)	0.03666 (9)
C15	0.70666 (16)	0.59240 (11)	0.23157 (11)	0.0305 (3)
C16	0.66349 (18)	0.70266 (12)	0.18864 (12)	0.0360 (3)
H16A	0.5583	0.7218	0.1969	0.054*
H16B	0.6661	0.7011	0.1202	0.054*
H16C	0.7379	0.7571	0.2208	0.054*
C21	0.63624 (16)	0.76555 (11)	0.40757 (10)	0.0291 (3)
C22	0.58983 (18)	0.87799 (11)	0.39537 (12)	0.0344 (3)
H22	0.4848	0.9012	0.3759	0.041*
C23	0.71239 (19)	0.94661 (12)	0.41473 (13)	0.0383 (3)
Cl23	0.70870 (6)	1.08626 (3)	0.40665 (5)	0.06566 (17)
S24	0.88643 (4)	0.88025 (3)	0.44916 (3)	0.03688 (10)
C25	0.79449 (17)	0.75478 (11)	0.43789 (11)	0.0315 (3)
C26	0.89306 (17)	0.65358 (13)	0.46486 (13)	0.0399 (4)
H26A	0.8314	0.5982	0.4901	0.060*
H26B	0.9848	0.6722	0.5138	0.060*
H26C	0.9267	0.6250	0.4081	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0294 (6)	0.0313 (6)	0.0288 (7)	0.0003 (5)	0.0082 (6)	0.0037 (5)
C2	0.0276 (6)	0.0330 (6)	0.0282 (7)	0.0022 (5)	0.0068 (5)	0.0033 (5)
C3	0.0321 (7)	0.0396 (7)	0.0401 (9)	0.0050 (5)	0.0143 (7)	0.0033 (6)
C4	0.0397 (9)	0.0454 (9)	0.0788 (15)	−0.0040 (7)	0.0275 (9)	−0.0007 (9)
C5	0.0347 (7)	0.0342 (7)	0.0476 (9)	−0.0036 (5)	0.0163 (7)	0.0024 (6)
C11	0.0293 (6)	0.0303 (6)	0.0281 (7)	−0.0013 (5)	0.0076 (5)	−0.0012 (5)
C12	0.0350 (7)	0.0329 (6)	0.0309 (8)	0.0011 (5)	0.0098 (6)	0.0012 (5)
C13	0.0346 (7)	0.0369 (7)	0.0325 (8)	0.0041 (5)	0.0077 (6)	−0.0020 (6)
Cl13	0.0505 (2)	0.0490 (2)	0.0484 (3)	0.01877 (17)	0.01241 (19)	−0.00181 (18)
S14	0.03619 (19)	0.04417 (19)	0.03302 (19)	0.00126 (14)	0.01509 (15)	−0.00018 (15)
C15	0.0299 (6)	0.0336 (6)	0.0288 (7)	−0.0023 (5)	0.0078 (6)	−0.0010 (5)
C16	0.0403 (8)	0.0370 (7)	0.0323 (8)	−0.0016 (6)	0.0111 (6)	0.0050 (6)
C21	0.0304 (7)	0.0328 (6)	0.0244 (6)	0.0019 (5)	0.0067 (5)	−0.0017 (5)
C22	0.0352 (7)	0.0328 (6)	0.0337 (8)	0.0032 (5)	0.0030 (6)	−0.0018 (6)
C23	0.0407 (8)	0.0322 (6)	0.0395 (9)	0.0000 (6)	0.0019 (7)	−0.0037 (6)
Cl23	0.0612 (3)	0.03293 (19)	0.0907 (4)	−0.00307 (17)	−0.0140 (3)	−0.0025 (2)
S24	0.03210 (18)	0.03865 (18)	0.0385 (2)	−0.00359 (13)	0.00378 (15)	−0.00760 (15)
C25	0.0312 (7)	0.0356 (7)	0.0282 (7)	0.0008 (5)	0.0067 (6)	−0.0044 (5)
C26	0.0300 (7)	0.0420 (7)	0.0433 (10)	0.0053 (6)	−0.0028 (7)	−0.0076 (7)

Geometric parameters (Å, º)

C1—C2	1.349 (2)	C13—S14	1.7239 (16)
C1—C11	1.466 (2)	S14—C15	1.7329 (15)
C1—C5	1.5113 (19)	C15—C16	1.5021 (19)
C2—C21	1.4688 (19)	C16—H16A	0.9800
C2—C3	1.510 (2)	C16—H16B	0.9800
C3—C4	1.530 (2)	C16—H16C	0.9800
C3—H3A	0.9900	C21—C25	1.373 (2)
C3—H3B	0.9900	C21—C22	1.4391 (19)
C4—C5	1.527 (2)	C22—C23	1.349 (2)
C4—H4A	0.9900	C22—H22	0.9500
C4—H4B	0.9900	C23—S24	1.7111 (16)
C5—H5A	0.9900	C23—Cl23	1.7175 (15)
C5—H5B	0.9900	S24—C25	1.7301 (15)
C11—C15	1.370 (2)	C25—C26	1.517 (2)
C11—C12	1.4384 (18)	C26—H26A	0.9800
C12—C13	1.347 (2)	C26—H26B	0.9800
C12—H12	0.9500	C26—H26C	0.9800
C13—Cl13	1.7165 (15)
C2—C1—C11	128.50 (13)	C12—C13—S14	112.62 (11)
C2—C1—C5	111.61 (13)	Cl13—C13—S14	120.83 (10)
C11—C1—C5	119.89 (12)	C13—S14—C15	91.29 (7)
C1—C2—C21	128.88 (13)	C11—C15—C16	129.35 (13)
C1—C2—C3	111.56 (12)	C11—C15—S14	111.37 (10)
C21—C2—C3	119.51 (12)	C16—C15—S14	119.28 (11)
C2—C3—C4	103.90 (13)	C15—C16—H16A	109.5
C2—C3—H3A	111.0	C15—C16—H16B	109.5
C4—C3—H3A	111.0	H16A—C16—H16B	109.5
C2—C3—H3B	111.0	C15—C16—H16C	109.5
C4—C3—H3B	111.0	H16A—C16—H16C	109.5
H3A—C3—H3B	109.0	H16B—C16—H16C	109.5
C5—C4—C3	107.24 (13)	C25—C21—C22	111.92 (12)
C5—C4—H4A	110.3	C25—C21—C2	126.45 (12)
C3—C4—H4A	110.3	C22—C21—C2	121.57 (12)
C5—C4—H4B	110.3	C23—C22—C21	112.34 (13)
C3—C4—H4B	110.3	C23—C22—H22	123.8
H4A—C4—H4B	108.5	C21—C22—H22	123.8
C1—C5—C4	103.60 (12)	C22—C23—S24	112.84 (11)
C1—C5—H5A	111.0	C22—C23—Cl23	127.29 (12)
C4—C5—H5A	111.0	S24—C23—Cl23	119.86 (9)
C1—C5—H5B	111.0	C23—S24—C25	91.47 (7)
C4—C5—H5B	111.0	C21—C25—C26	130.23 (13)
H5A—C5—H5B	109.0	C21—C25—S24	111.41 (10)
C15—C11—C12	112.32 (13)	C26—C25—S24	118.32 (11)
C15—C11—C1	125.76 (12)	C25—C26—H26A	109.5
C12—C11—C1	121.89 (13)	C25—C26—H26B	109.5
C13—C12—C11	112.36 (13)	H26A—C26—H26B	109.5
C13—C12—H12	123.8	C25—C26—H26C	109.5
C11—C12—H12	123.8	H26A—C26—H26C	109.5
C12—C13—Cl13	126.55 (12)	H26B—C26—H26C	109.5
C11—C1—C2—C21	−6.2 (3)	C1—C11—C15—C16	0.0 (2)
C5—C1—C2—C21	173.75 (14)	C12—C11—C15—S14	−1.53 (16)
C11—C1—C2—C3	176.31 (14)	C1—C11—C15—S14	−179.65 (11)
C5—C1—C2—C3	−3.76 (18)	C13—S14—C15—C11	0.49 (11)
C1—C2—C3—C4	−5.63 (18)	C13—S14—C15—C16	−179.20 (12)
C21—C2—C3—C4	176.60 (14)	C1—C2—C21—C25	−42.6 (2)
C2—C3—C4—C5	12.51 (19)	C3—C2—C21—C25	134.70 (16)
C2—C1—C5—C4	11.48 (19)	C1—C2—C21—C22	140.41 (16)
C11—C1—C5—C4	−168.58 (15)	C3—C2—C21—C22	−42.2 (2)
C3—C4—C5—C1	−14.5 (2)	C25—C21—C22—C23	1.2 (2)
C2—C1—C11—C15	−49.2 (2)	C2—C21—C22—C23	178.51 (14)
C5—C1—C11—C15	130.91 (16)	C21—C22—C23—S24	−0.60 (19)
C2—C1—C11—C12	132.89 (16)	C21—C22—C23—Cl23	178.51 (13)
C5—C1—C11—C12	−47.0 (2)	C22—C23—S24—C25	−0.06 (14)
C15—C11—C12—C13	2.13 (18)	Cl23—C23—S24—C25	−179.24 (12)
C1—C11—C12—C13	−179.67 (13)	C22—C21—C25—C26	176.34 (16)
C11—C12—C13—Cl13	178.61 (11)	C2—C21—C25—C26	−0.9 (3)
C11—C12—C13—S14	−1.75 (17)	C22—C21—C25—S24	−1.18 (17)
C12—C13—S14—C15	0.75 (12)	C2—C21—C25—S24	−178.38 (12)
Cl13—C13—S14—C15	−179.58 (10)	C23—S24—C25—C21	0.73 (13)
C12—C11—C15—C16	178.11 (14)	C23—S24—C25—C26	−177.12 (13)