Bis(4-chloro­methyl-2,5-di­methyl-3-thienyl)­methane

In the title compound, C₁₅H₁₈Cl₂S₂, the mol­ecule has a crystallographic twofold axis. The dihedral angle between the symmetry-related thio­phene rings is 85.54 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.102
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RADNW01_ALERT_1_C  The radiation wavelength lies outside the expected range
            for the supplied radiation type. Expected range 1.54175-1.54180
            Wavelength given =    1.54190
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B    ..  CG1     ..       3.16 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C8     ..  CG1     ..       4.06 Ang.

Alert level G
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.50
            Tmin and Tmax reported:      0.431     0.475
            Tmin and Tmax expected:      0.224     0.475
            RR =      1.922
            Please check that your absorption correction is appropriate.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Bis(4-chloromethyl-2,5-dimethyl-3-thienyl)methane

Crystal data

C15H18Cl2S2	F(000) = 696.00
Mr = 333.33	Dx = 1.443 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5419 Å
Hall symbol: -C 2yc	Cell parameters from 8753 reflections
a = 20.797 (4) Å	θ = 3.0–68.2°
b = 5.068 (1) Å	µ = 6.20 mm^−1
c = 16.253 (3) Å	T = 123 K
β = 116.42 (1)°	Prism, colorless
V = 1534.1 (5) Å^3	0.30 × 0.30 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1278 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.048
ω scans	θmax = 68.2°
Absorption correction: numerical (ABSCOR; Higashi, 1999)	h = −24→24
Tmin = 0.431, Tmax = 0.475	k = −5→5
9291 measured reflections	l = −19→18
1382 independent reflections

Refinement

Refinement on F^2	w = 1/[0.001Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.030	(Δ/σ)max < 0.001
wR(F^2) = 0.102	Δρmax = 0.36 e Å^−3
S = 1.00	Δρmin = −0.43 e Å^−3
1382 reflections	Extinction correction: Larson (1970)
99 parameters	Extinction coefficient: 44 (4)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.41765 (2)	0.32981 (9)	0.91105 (3)	0.0212 (2)
S1	0.31083 (2)	0.50041 (9)	0.57996 (3)	0.0172 (2)
C1	0.38518 (9)	0.3001 (4)	0.6110 (1)	0.0149 (5)
C2	0.43116 (9)	0.3300 (3)	0.7021 (1)	0.0128 (5)
C3	0.40509 (9)	0.5166 (4)	0.7469 (1)	0.0129 (5)
C4	0.3404 (1)	0.6271 (4)	0.6889 (1)	0.0163 (5)
C5	0.3917 (1)	0.1255 (4)	0.5404 (1)	0.0201 (5)
C6	0.50000 (1)	0.1725 (5)	0.75000 (1)	0.0146 (7)
C7	0.44152 (9)	0.5762 (4)	0.8471 (1)	0.0152 (5)
C8	0.2968 (1)	0.8294 (4)	0.7095 (1)	0.0223 (5)
H5A	0.3928	−0.0539	0.5579	0.025*
H5B	0.4345	0.1674	0.5359	0.024*
H5C	0.3515	0.1537	0.4826	0.025*
H6	0.4952	0.0643	0.7947	0.017*
H7A	0.4269	0.7456	0.8573	0.019*
H7B	0.4920	0.5750	0.8679	0.018*
H8A	0.2472	0.7946	0.6729	0.028*
H8B	0.3079	1.0008	0.6960	0.028*
H8C	0.3074	0.8197	0.7727	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0241 (3)	0.0235 (4)	0.0172 (3)	−0.0048 (2)	0.0102 (2)	0.0009 (2)
S1	0.0112 (3)	0.0202 (4)	0.0152 (3)	−0.0003 (2)	0.0013 (2)	0.0007 (2)
C1	0.0117 (9)	0.016 (1)	0.0156 (9)	−0.0027 (7)	0.0051 (7)	−0.0008 (7)
C2	0.0100 (9)	0.014 (1)	0.0143 (9)	−0.0029 (6)	0.0052 (7)	−0.0003 (7)
C3	0.0108 (8)	0.012 (1)	0.0150 (9)	−0.0026 (6)	0.0053 (7)	0.0008 (7)
C4	0.0140 (9)	0.016 (1)	0.018 (1)	−0.0036 (7)	0.0066 (8)	−0.0011 (7)
C5	0.0190 (9)	0.022 (1)	0.018 (1)	−0.0066 (8)	0.0075 (8)	−0.0062 (8)
C6	0.013 (1)	0.014 (1)	0.017 (1)	0.0000	0.006 (1)	0.0000
C7	0.0156 (9)	0.015 (1)	0.0159 (9)	−0.0030 (8)	0.0077 (7)	−0.0014 (8)
C8	0.0157 (9)	0.021 (1)	0.030 (1)	0.0024 (7)	0.0103 (9)	−0.0006 (8)

Geometric parameters (Å, º)

Cl1—C7	1.828 (2)	C6—C2	1.517 (2)
S1—C1	1.727 (2)	C5—H5A	0.9500
S1—C4	1.719 (2)	C5—H5B	0.9500
C1—C2	1.366 (2)	C5—H5C	0.9500
C1—C5	1.503 (3)	C6—H6	0.9501
C2—C3	1.439 (3)	C7—H7A	0.9500
C2—C6	1.517 (2)	C7—H7B	0.9500
C3—C4	1.372 (2)	C8—H8A	0.9500
C3—C7	1.491 (3)	C8—H8B	0.9501
C4—C8	1.504 (3)	C8—H8C	0.9500
Cl1···C2	3.530 (2)	C2···H7A	3.3179
Cl1···C3	2.732 (2)	C2···H7B	2.7158
Cl1···C4	3.567 (2)	C2···H8B^iv	3.0227
Cl1···C5^i	3.324 (2)	C3···H6	2.8421
S1···C2	2.555 (2)	C3···H6^v	3.2442
S1···C3	2.545 (2)	C3···H7A	2.0121
S1···C5	2.795 (2)	C3···H7B	2.0158
S1···C8	2.801 (2)	C3···H8A	3.2713
C1···C3	2.331 (3)	C3···H8B	3.0500
C1···C4	2.502 (3)	C3···H8B^iv	3.1802
C1···C6	2.534 (2)	C3···H8C	2.7243
C2···C4	2.348 (3)	C4···H5A^v	3.2244
C2···C5	2.595 (3)	C4···H7A	2.5893
C2···C7	2.590 (3)	C4···H7B	3.2116
C3···C6	2.617 (3)	C4···H8A	2.0254
C3···C8	2.596 (3)	C4···H8B	2.0321
C4···C7	2.508 (2)	C4···H8B^iv	3.2579
C5···C6	3.148 (2)	C4···H8C	2.0282
C6···C1	2.534 (2)	C6···H5A	3.1365
C6···C3	2.617 (3)	C6···H5B	3.1221
C6···C5	3.148 (2)	C6···H7A^iv	3.5203
C6···C7	3.141 (3)	C6···H7B	2.8539
C7···C6	3.141 (3)	C7···H5B^ii	3.3941
C7···C8	3.118 (2)	C7···H6	3.0905
Cl1···H5C^i	3.2672	C7···H6^v	2.9900
Cl1···H5C^ii	3.3941	C7···H8B	3.5086
Cl1···H8A^iii	3.0794	C7···H8C	2.7867
Cl1···H8C^iv	3.5231	C8···H7A	2.7360
Cl1···H8C	3.4484	C8···H8A^vii	3.4061
Cl1···H7A^iv	3.1170	C8···H8B^iii	3.5834
Cl1···H7A	2.3219	C8···H8C^iii	3.4647
Cl1···H7B	2.3224	C8···H8C^vii	3.3922
Cl1···H5A^i	3.0025	H5A···S1^iv	2.9469
Cl1···H5B^i	3.1555	H5A···C1^iv	3.4075
Cl1···H5B^ii	3.1780	H5A···C4^iv	3.2244
Cl1···H6	3.2719	H5A···C6	3.1365
S1···H5A	3.3872	H5B···C6	3.1221
S1···H5A^v	2.9469	H5C···S1^vi	3.1597
S1···H5B	3.4083	H6···C3^iv	3.2442
S1···H5C	2.7381	H6···C7^iv	2.9900
S1···H5C^vi	3.1597	H7A···Cl1^v	3.1170
S1···H8A	2.8346	H7A···C5^ii	3.4289
S1···H8B	3.1775	H7A···C6^v	3.5203
S1···H8B^iv	3.1741	H7B···C6	2.8539
S1···H8C	3.5542	H8A···Cl1^vii	3.0794
C1···H5A	2.0280	H8A···C8^iii	3.4061
C1···H5A^v	3.4075	H8B···S1^v	3.1741
C1···H5B	2.0277	H8B···C1^v	2.9607
C1···H5C	2.0247	H8B···C2^v	3.0227
C1···H6	3.0819	H8B···C3^v	3.1802
C1···H8B^iv	2.9607	H8B···C4^v	3.2579
C2···H5A	2.8718	H8B···C8^vii	3.5834
C2···H5B	2.8540	H8C···Cl1^v	3.5231
C2···H5C	3.3182	H8C···C8^iii	3.3922
C2···H6	2.0175	H8C···C8^vii	3.4647
Cl1—C7—C3	110.4 (1)	C1—C5—H5A	109.4713
S1—C1—C2	110.9 (2)	C1—C5—H5B	109.4480
C4—S1—C1	93.11 (9)	C2—C6—H6	107.4986
S1—C1—C5	119.7 (1)	C3—C7—H7A	109.0512
S1—C4—C3	110.4 (2)	C3—C7—H7B	109.3703
S1—C4—C8	120.6 (1)	C4—C8—H8C	109.4328
C1—C2—C3	112.4 (2)	C4—C8—H8A	109.1926
C5—C1—C2	129.4 (2)	C4—C8—H8B	109.7638
C1—C2—C6	122.9 (2)	H5A—C5—H5C	109.5758
C2—C3—C4	113.3 (2)	H5B—C5—H5C	109.4664
C2—C3—C7	124.3 (1)	H5B—C5—H5A	109.6815
C6—C2—C3	124.6 (1)	H7B—C7—H7A	109.4621
C7—C3—C4	122.3 (2)	H8C—C8—H8A	109.4846
C3—C4—C8	129.0 (2)	H8B—C8—H8A	109.4812
Cl1—C7—H7A	109.2511	H8B—C8—H8C	109.4718
Cl1—C7—H7B	109.2955	C2—C6—C2^viii	116.5 (2)
C1—C5—H5C	109.1831
C4—S1—C1—C2	−0.0 (1)	C1—C2—C3—C7	175.9 (2)
C4—S1—C1—C5	180.0 (1)	C6—C2—C3—C4	−178.1 (2)
C1—S1—C4—C3	−0.4 (2)	C6—C2—C3—C7	−1.4 (3)
C1—S1—C4—C8	179.8 (2)	C2—C3—C4—S1	0.7 (2)
S1—C1—C2—C3	0.4 (2)	C2—C3—C4—C8	−179.5 (2)
S1—C1—C2—C6	177.8 (2)	C7—C3—C4—S1	−176.0 (2)
C5—C1—C2—C3	−179.5 (2)	C7—C3—C4—C8	3.8 (4)
C5—C1—C2—C6	−2.1 (3)	C2—C3—C7—Cl1	−82.6 (2)
C1—C2—C3—C4	−0.8 (3)	C4—C3—C7—Cl1	93.8 (2)

Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y+1, z+1/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) x, y−1, z; (v) x, y+1, z; (vi) −x+1/2, −y+1/2, −z+1; (vii) −x+1/2, y+1/2, −z+3/2; (viii) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1^v	0.95	2.84	3.767 (2)	166
C8—H8B···Cg1^iv	0.95	3.16	4.060 (2)	158

Symmetry codes: (iv) x, y−1, z; (v) x, y+1, z.