2,4,7-Trimethyl-3,8-bis­(methyl­sulfan­yl)benzo[1,2-b:5,6-b']difuran

The title compound, C₁₅H₁₆O₂S₂, was prepared by the Lewis acid-catalysed reaction of 5-methyl­resorcinol with α-chloro-α-(methyl­sulfan­yl)acetone. In the crystal structure, aromatic π–π stacking inter­actions are not observed between adjacent mol­ecules, because of steric hindrance induced by the five methyl groups in the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.167
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   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

   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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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.

2,4,7-Trimethyl-3,8-bis(methylsulfanyl)benzo[1,2 - b:5,6 - b']difuran

Crystal data

C15H16O2S2	Z = 2
Mr = 292.40	F(000) = 308
Triclinic, P1	Dx = 1.342 Mg m^−3
Hall symbol: -P 1	Melting point = 375–377 K
a = 7.7512 (6) Å	Mo Kα radiation, λ = 0.71069 Å
b = 9.8886 (8) Å	Cell parameters from 36 reflections
c = 10.6471 (9) Å	θ = 8.7–14.0°
α = 72.280 (8)°	µ = 0.36 mm^−1
β = 71.435 (8)°	T = 298 K
γ = 74.554 (7)°	Block, colourless
V = 723.8 (1) Å^3	0.32 × 0.25 × 0.23 mm

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.1°
Graphite monochromator	h = −9→10
ω/2θ scans	k = −11→12
3302 measured reflections	l = 0→13
3302 independent reflections	3 standard reflections every 60 min
2226 reflections with I > 2σ(I)	intensity decay: 2.4%

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 0.6399P] where P = (Fo^2 + 2Fc^2)/3
3302 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.26936 (15)	0.03713 (12)	1.20429 (10)	0.0603 (3)
S2	0.25350 (16)	0.24649 (12)	0.47260 (10)	0.0610 (3)
O1	0.2492 (3)	0.0872 (2)	0.8271 (2)	0.0454 (6)
O2	0.2396 (4)	0.5819 (3)	0.6067 (2)	0.0533 (6)
C1	0.2538 (5)	0.0115 (4)	0.9594 (3)	0.0457 (8)
C2	0.2548 (5)	0.1000 (4)	1.0343 (3)	0.0452 (8)
C3	0.2508 (4)	0.2452 (4)	0.9452 (3)	0.0421 (7)
C4	0.2500 (5)	0.3831 (4)	0.9608 (3)	0.0456 (8)
C5	0.2445 (5)	0.4987 (4)	0.8479 (4)	0.0496 (8)
H5	0.2426	0.5911	0.8536	0.060*
C6	0.2419 (5)	0.4757 (4)	0.7265 (3)	0.0458 (8)
C7	0.2442 (5)	0.5141 (4)	0.5094 (4)	0.0501 (9)
C8	0.2478 (5)	0.3710 (4)	0.5627 (3)	0.0472 (8)
C9	0.2456 (4)	0.3435 (4)	0.7058 (3)	0.0413 (7)
C10	0.2481 (4)	0.2286 (4)	0.8201 (3)	0.0408 (7)
C11	0.2545 (6)	−0.1454 (4)	0.9912 (4)	0.0596 (10)
H11A	0.2826	−0.1916	1.0776	0.089*
H11B	0.3465	−0.1867	0.9213	0.089*
H11C	0.1348	−0.1595	0.9954	0.089*
C12	0.0290 (7)	0.0804 (6)	1.2948 (4)	0.0790 (14)
H12A	−0.0191	0.1805	1.2606	0.118*
H12B	0.0192	0.0623	1.3904	0.118*
H12C	−0.0409	0.0214	1.2814	0.118*
C13	0.2546 (6)	0.4082 (4)	1.0926 (4)	0.0583 (10)
H13A	0.2434	0.5098	1.0827	0.087*
H13B	0.3698	0.3573	1.1139	0.087*
H13C	0.1536	0.3736	1.1649	0.087*
C14	0.2479 (6)	0.6085 (5)	0.3708 (4)	0.0627 (11)
H14A	0.3598	0.6472	0.3347	0.094*
H14B	0.1428	0.6863	0.3756	0.094*
H14C	0.2434	0.5531	0.3122	0.094*
C15	0.4977 (7)	0.1847 (6)	0.4163 (6)	0.1006 (19)
H15A	0.5560	0.2653	0.3615	0.151*
H15B	0.5205	0.1159	0.3632	0.151*
H15C	0.5476	0.1398	0.4941	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0710 (7)	0.0648 (6)	0.0474 (5)	−0.0144 (5)	−0.0272 (5)	−0.0027 (4)
S2	0.0747 (7)	0.0744 (7)	0.0467 (5)	−0.0288 (5)	−0.0154 (5)	−0.0202 (5)
O1	0.0522 (14)	0.0439 (13)	0.0439 (13)	−0.0121 (11)	−0.0130 (11)	−0.0129 (10)
O2	0.0650 (17)	0.0475 (14)	0.0475 (14)	−0.0157 (12)	−0.0140 (12)	−0.0080 (11)
C1	0.0412 (19)	0.046 (2)	0.0464 (19)	−0.0076 (15)	−0.0106 (15)	−0.0070 (15)
C2	0.0462 (19)	0.049 (2)	0.0417 (18)	−0.0078 (15)	−0.0143 (15)	−0.0099 (15)
C3	0.0410 (18)	0.0457 (19)	0.0406 (17)	−0.0091 (14)	−0.0106 (14)	−0.0111 (14)
C4	0.0453 (19)	0.051 (2)	0.0434 (19)	−0.0081 (16)	−0.0098 (15)	−0.0188 (16)
C5	0.055 (2)	0.045 (2)	0.053 (2)	−0.0107 (16)	−0.0125 (17)	−0.0183 (16)
C6	0.050 (2)	0.0423 (19)	0.0445 (18)	−0.0094 (15)	−0.0119 (15)	−0.0088 (15)
C7	0.053 (2)	0.058 (2)	0.0418 (19)	−0.0141 (17)	−0.0129 (16)	−0.0113 (16)
C8	0.049 (2)	0.057 (2)	0.0388 (18)	−0.0146 (16)	−0.0105 (15)	−0.0126 (15)
C9	0.0416 (18)	0.0452 (19)	0.0389 (16)	−0.0108 (14)	−0.0104 (14)	−0.0105 (14)
C10	0.0400 (18)	0.0425 (18)	0.0414 (17)	−0.0106 (14)	−0.0077 (14)	−0.0127 (14)
C11	0.065 (3)	0.046 (2)	0.067 (2)	−0.0103 (18)	−0.018 (2)	−0.0112 (18)
C12	0.089 (3)	0.104 (4)	0.043 (2)	−0.037 (3)	−0.006 (2)	−0.012 (2)
C13	0.074 (3)	0.060 (2)	0.049 (2)	−0.014 (2)	−0.0190 (19)	−0.0202 (18)
C14	0.070 (3)	0.065 (3)	0.048 (2)	−0.019 (2)	−0.0178 (19)	0.0002 (18)
C15	0.083 (4)	0.106 (4)	0.126 (5)	−0.032 (3)	0.008 (3)	−0.070 (4)

Geometric parameters (Å, º)

S1—C2	1.755 (3)	C7—C14	1.483 (5)
S1—C12	1.807 (5)	C8—C9	1.459 (5)
S2—C8	1.761 (4)	C9—C10	1.391 (4)
S2—C15	1.789 (5)	C11—H11A	0.9600
O1—C10	1.375 (4)	C11—H11B	0.9600
O1—C1	1.386 (4)	C11—H11C	0.9600
O2—C7	1.382 (4)	C12—H12A	0.9600
O2—C6	1.386 (4)	C12—H12B	0.9600
C1—C2	1.355 (5)	C12—H12C	0.9600
C1—C11	1.482 (5)	C13—H13A	0.9600
C2—C3	1.459 (5)	C13—H13B	0.9600
C3—C10	1.399 (4)	C13—H13C	0.9600
C3—C4	1.420 (5)	C14—H14A	0.9600
C4—C5	1.387 (5)	C14—H14B	0.9600
C4—C13	1.511 (5)	C14—H14C	0.9600
C5—C6	1.385 (5)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C9	1.382 (5)	C15—H15C	0.9600
C7—C8	1.351 (5)
C2—S1—C12	100.96 (19)	O1—C10—C3	111.2 (3)
C8—S2—C15	101.0 (2)	C9—C10—C3	122.5 (3)
C10—O1—C1	106.0 (3)	C1—C11—H11A	109.5
C7—O2—C6	106.7 (3)	C1—C11—H11B	109.5
C2—C1—O1	111.3 (3)	H11A—C11—H11B	109.5
C2—C1—C11	133.1 (3)	C1—C11—H11C	109.5
O1—C1—C11	115.6 (3)	H11A—C11—H11C	109.5
C1—C2—C3	107.1 (3)	H11B—C11—H11C	109.5
C1—C2—S1	122.9 (3)	S1—C12—H12A	109.5
C3—C2—S1	130.0 (3)	S1—C12—H12B	109.5
C10—C3—C4	120.6 (3)	H12A—C12—H12B	109.5
C10—C3—C2	104.4 (3)	S1—C12—H12C	109.5
C4—C3—C2	135.0 (3)	H12A—C12—H12C	109.5
C5—C4—C3	117.3 (3)	H12B—C12—H12C	109.5
C5—C4—C13	119.5 (3)	C4—C13—H13A	109.5
C3—C4—C13	123.3 (3)	C4—C13—H13B	109.5
C6—C5—C4	119.6 (3)	H13A—C13—H13B	109.5
C6—C5—H5	120.2	C4—C13—H13C	109.5
C4—C5—H5	120.2	H13A—C13—H13C	109.5
C9—C6—C5	125.3 (3)	H13B—C13—H13C	109.5
C9—C6—O2	109.9 (3)	C7—C14—H14A	109.5
C5—C6—O2	124.8 (3)	C7—C14—H14B	109.5
C8—C7—O2	111.1 (3)	H14A—C14—H14B	109.5
C8—C7—C14	133.3 (3)	C7—C14—H14C	109.5
O2—C7—C14	115.7 (3)	H14A—C14—H14C	109.5
C7—C8—C9	106.5 (3)	H14B—C14—H14C	109.5
C7—C8—S2	125.2 (3)	S2—C15—H15A	109.5
C9—C8—S2	128.2 (3)	S2—C15—H15B	109.5
C6—C9—C10	114.8 (3)	H15A—C15—H15B	109.5
C6—C9—C8	105.8 (3)	S2—C15—H15C	109.5
C10—C9—C8	139.4 (3)	H15A—C15—H15C	109.5
O1—C10—C9	126.3 (3)	H15B—C15—H15C	109.5
C3—C10—O1—C1	−0.3 (3)	C9—C6—O2—C7	−0.7 (4)
C4—C2—C3—C10	179.8 (6)	C6—C9—C8—C7	−0.4 (4)
C10—O1—C1—C2	0.2 (4)	C6—O2—C7—C8	0.5 (4)
C2—C3—C10—O1	0.3 (4)	C8—C9—C6—O2	0.7 (4)
O1—C1—C2—C3	−0.1 (4)	O2—C7—C8—C9	−0.1 (4)