2,6-Dimethyl-3,7-bis­(methyl­sulfan­yl)benzo[1,2-b:4,5-b′]difuran

In the centrosymmetric mol­ecule of the title compound, C₁₄H₁₄O₂S₂, the benzo[1,2-b:4,5-b′]difuran group is almost planar. The structure is stabilized by aromatic π–π stacking and —CH₂—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.147
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C6

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED32 (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

2,6-Dimethyl-3,7-bis(methylsulfanyl)benzo[1,2 - b:4,5 - b']difuran

Crystal data

C14H14O2S2	Z = 1
Mr = 278.37	F(000) = 146
Triclinic, P1	Dx = 1.384 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.2073 (5) Å	Cell parameters from 29 reflections
b = 8.2548 (6) Å	θ = 9.5–10.9°
c = 8.5234 (6) Å	µ = 0.39 mm^−1
α = 105.616 (6)°	T = 298 K
β = 98.690 (7)°	Prism, colorless
γ = 103.564 (6)°	0.50 × 0.31 × 0.29 mm
V = 333.91 (5) Å^3

Data collection

Stoe Stadi-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.6°
Graphite monochromator	h = −6→6
ω/2–θ scans	k = −10→10
1530 measured reflections	l = 0→11
1530 independent reflections	3 standard reflections every 60 min
1339 reflections with I > 2σ(I)	intensity decay: 1.6%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0799P)^2 + 0.3086P] where P = (Fo^2 + 2Fc^2)/3
1530 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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
S1	0.69578 (13)	0.44296 (8)	0.20744 (9)	0.0479 (3)
O1	0.3839 (3)	−0.0308 (2)	0.2344 (2)	0.0409 (4)
C1	−0.0568 (5)	−0.1670 (3)	0.0343 (3)	0.0378 (5)
H1	−0.0898	−0.2729	0.0573	0.045*
C2	0.1767 (5)	−0.0291 (3)	0.1131 (3)	0.0360 (5)
C3	0.2385 (5)	0.1336 (3)	0.0827 (3)	0.0354 (5)
C4	0.4998 (5)	0.2346 (3)	0.1951 (3)	0.0380 (5)
C5	0.5758 (5)	0.1314 (3)	0.2821 (3)	0.0396 (5)
C6	0.8191 (5)	0.1595 (4)	0.4122 (4)	0.0508 (6)
H6A	0.8040	0.0562	0.4459	0.061*
H6B	0.8333	0.2580	0.5072	0.061*
H6C	0.9780	0.1823	0.3680	0.061*
C7	0.4906 (7)	0.5804 (4)	0.2864 (4)	0.0602 (8)
H7A	0.5800	0.7003	0.2985	0.072*
H7B	0.4655	0.5711	0.3933	0.072*
H7C	0.3172	0.5429	0.2095	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0395 (4)	0.0336 (4)	0.0666 (5)	0.0045 (2)	0.0132 (3)	0.0144 (3)
O1	0.0454 (9)	0.0345 (8)	0.0432 (9)	0.0115 (7)	0.0057 (7)	0.0153 (7)
C1	0.0449 (13)	0.0269 (10)	0.0428 (12)	0.0086 (9)	0.0119 (10)	0.0132 (9)
C2	0.0413 (12)	0.0312 (11)	0.0369 (11)	0.0108 (9)	0.0107 (9)	0.0118 (9)
C3	0.0396 (11)	0.0274 (10)	0.0384 (11)	0.0077 (9)	0.0117 (9)	0.0093 (8)
C4	0.0392 (11)	0.0308 (11)	0.0424 (12)	0.0076 (9)	0.0120 (9)	0.0100 (9)
C5	0.0398 (12)	0.0360 (12)	0.0399 (12)	0.0109 (9)	0.0092 (9)	0.0069 (9)
C6	0.0462 (14)	0.0536 (15)	0.0510 (15)	0.0174 (12)	0.0060 (11)	0.0143 (12)
C7	0.0611 (18)	0.0392 (14)	0.078 (2)	0.0173 (13)	0.0151 (15)	0.0120 (13)

Geometric parameters (Å, º)

S1—C4	1.749 (2)	C3—C4	1.452 (3)
S1—C7	1.805 (3)	C4—C5	1.357 (3)
O1—C2	1.383 (3)	C5—C6	1.479 (3)
O1—C5	1.383 (3)	C6—H6A	0.9600
C1—C2	1.385 (3)	C6—H6B	0.9600
C1—C3^i	1.397 (3)	C6—H6C	0.9600
C1—H1	0.9300	C7—H7A	0.9600
C2—C3	1.408 (3)	C7—H7B	0.9600
C3—C1^i	1.397 (3)	C7—H7C	0.9600
C4—S1—C7	102.1 (1)	C4—C5—C6	132.6 (2)
C2—O1—C5	106.8 (2)	O1—C5—C6	116.3 (2)
C2—C1—C3^i	114.4 (2)	C5—C6—H6A	109.5
C2—C1—H1	122.8	C5—C6—H6B	109.5
C3^i—C1—H1	122.8	H6A—C6—H6B	109.5
O1—C2—C1	124.8 (2)	C5—C6—H6C	109.5
O1—C2—C3	109.8 (2)	H6A—C6—H6C	109.5
C1—C2—C3	125.4 (2)	H6B—C6—H6C	109.5
C1^i—C3—C2	120.3 (2)	S1—C7—H7A	109.5
C1^i—C3—C4	134.5 (2)	S1—C7—H7B	109.5
C2—C3—C4	105.2 (2)	H7A—C7—H7B	109.5
C5—C4—C3	107.0 (2)	S1—C7—H7C	109.5
C5—C4—S1	125.5 (2)	H7A—C7—H7C	109.5
C3—C4—S1	127.3 (2)	H7B—C7—H7C	109.5
C4—C5—O1	111.2 (2)
C3—C2—O1—C5	0.6 (2)	C5—C4—C3—C2	0.0 (3)
C2—O1—C5—C4	−0.6 (3)	C4—C3—C2—O1	−0.4 (2)
O1—C5—C4—C3	0.3 (2)

Symmetry code: (i) −x, −y, −z.