The title compound, C
11H
10O
4S, was prepared by oxidation of 2-methyl-5,6-methylenedioxy-3-methylsulfanyl-1-benzofuran using 3-chloroperbenzoic acid. The 5,6-methylenedioxybenzofuran ring system is almost planar. The crystal structure contains aromatic π—π stacking and CH
2—H
π interactions.
Supporting information
CCDC reference: 646769
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.006 Å
- R factor = 0.095
- wR factor = 0.202
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C11 H10 O4 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Crystal data top
C11H10O4S | F(000) = 496 |
Mr = 238.25 | Dx = 1.510 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p_2yn | Cell parameters from 3245 reflections |
a = 5.0453 (5) Å | θ = 2.5–27.9° |
b = 12.642 (1) Å | µ = 0.30 mm−1 |
c = 16.508 (2) Å | T = 173 K |
β = 95.556 (2)° | Needle, colorless |
V = 1047.98 (18) Å3 | 0.65 × 0.10 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 2023 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
Detector resolution: 10.00 pixels mm-1 | h = −6→6 |
φ and ω scans | k = −11→15 |
6212 measured reflections | l = −21→20 |
2261 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.095 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.35 | w = 1/[σ2(Fo2) + (0.0344P)2 + 3.5071P] where P = (Fo2 + 2Fc2)/3 |
2261 reflections | (Δ/σ)max < 0.001 |
146 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S | −0.0088 (2) | 0.68631 (9) | 0.43950 (6) | 0.0228 (3) | |
O1 | 0.2102 (6) | 0.7178 (3) | 0.67368 (16) | 0.0234 (7) | |
O2 | −0.4040 (8) | 0.9863 (3) | 0.7567 (2) | 0.0423 (10) | |
O3 | −0.5856 (7) | 1.0046 (3) | 0.62387 (18) | 0.0323 (8) | |
O4 | −0.3039 (7) | 0.6888 (3) | 0.41868 (19) | 0.0339 (9) | |
C1 | 0.0492 (8) | 0.7245 (4) | 0.5427 (2) | 0.0184 (9) | |
C2 | −0.0948 (8) | 0.8015 (3) | 0.5854 (2) | 0.0194 (9) | |
C3 | −0.3026 (9) | 0.8740 (4) | 0.5638 (2) | 0.0217 (9) | |
H3 | −0.3773 | 0.8827 | 0.5104 | 0.026* | |
C4 | −0.3858 (9) | 0.9306 (4) | 0.6274 (2) | 0.0221 (9) | |
C5 | −0.5898 (10) | 1.0449 (4) | 0.7045 (3) | 0.0282 (10) | |
H5A | −0.5420 | 1.1192 | 0.7059 | 0.034* | |
H5B | −0.7669 | 1.0378 | 0.7220 | 0.034* | |
C6 | −0.2749 (9) | 0.9190 (4) | 0.7078 (2) | 0.0251 (10) | |
C7 | −0.0718 (9) | 0.8511 (4) | 0.7310 (2) | 0.0254 (10) | |
H7 | 0.0027 | 0.8441 | 0.7845 | 0.030* | |
C8 | 0.0127 (8) | 0.7931 (3) | 0.6663 (2) | 0.0197 (9) | |
C9 | 0.2279 (9) | 0.6754 (4) | 0.5977 (2) | 0.0230 (9) | |
C10 | 0.4201 (10) | 0.5895 (4) | 0.5914 (3) | 0.0307 (11) | |
H10A | 0.3769 | 0.5316 | 0.6255 | 0.037* | |
H10B | 0.5961 | 0.6146 | 0.6087 | 0.037* | |
H10C | 0.4130 | 0.5660 | 0.5359 | 0.037* | |
C11 | 0.1156 (10) | 0.8016 (4) | 0.3941 (3) | 0.0308 (11) | |
H11A | 0.0721 | 0.7989 | 0.3362 | 0.046* | |
H11B | 0.3055 | 0.8048 | 0.4060 | 0.046* | |
H11C | 0.0362 | 0.8633 | 0.4155 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0259 (6) | 0.0285 (6) | 0.0131 (5) | 0.0007 (5) | −0.0022 (4) | −0.0053 (4) |
O1 | 0.0268 (16) | 0.0288 (18) | 0.0134 (13) | 0.0006 (13) | −0.0036 (11) | 0.0068 (12) |
O2 | 0.054 (2) | 0.053 (2) | 0.0193 (16) | 0.017 (2) | −0.0041 (15) | −0.0172 (16) |
O3 | 0.043 (2) | 0.035 (2) | 0.0184 (15) | 0.0111 (16) | −0.0044 (14) | −0.0067 (14) |
O4 | 0.0323 (18) | 0.050 (2) | 0.0185 (15) | −0.0066 (17) | −0.0011 (13) | −0.0051 (15) |
C1 | 0.022 (2) | 0.022 (2) | 0.0110 (17) | −0.0060 (17) | −0.0008 (15) | −0.0010 (15) |
C2 | 0.023 (2) | 0.021 (2) | 0.0130 (18) | −0.0077 (18) | −0.0009 (15) | 0.0005 (16) |
C3 | 0.028 (2) | 0.026 (2) | 0.0097 (17) | −0.0011 (19) | −0.0024 (15) | 0.0006 (16) |
C4 | 0.023 (2) | 0.023 (2) | 0.019 (2) | −0.0013 (18) | −0.0041 (16) | 0.0016 (17) |
C5 | 0.034 (3) | 0.030 (3) | 0.022 (2) | −0.002 (2) | 0.0056 (18) | −0.0044 (19) |
C6 | 0.033 (2) | 0.029 (3) | 0.0125 (19) | −0.009 (2) | 0.0005 (17) | −0.0029 (17) |
C7 | 0.034 (3) | 0.031 (3) | 0.0101 (18) | −0.010 (2) | −0.0050 (17) | 0.0021 (17) |
C8 | 0.021 (2) | 0.023 (2) | 0.0134 (18) | −0.0057 (17) | −0.0042 (15) | 0.0043 (16) |
C9 | 0.025 (2) | 0.024 (2) | 0.0185 (19) | −0.0072 (19) | −0.0014 (16) | 0.0045 (17) |
C10 | 0.033 (3) | 0.033 (3) | 0.025 (2) | 0.005 (2) | −0.0027 (19) | 0.004 (2) |
C11 | 0.031 (2) | 0.040 (3) | 0.022 (2) | −0.003 (2) | 0.0034 (18) | 0.006 (2) |
Geometric parameters (Å, º) top
S—O4 | 1.495 (4) | C3—H3 | 0.9300 |
S—C1 | 1.767 (4) | C4—C6 | 1.397 (6) |
S—C11 | 1.781 (5) | C5—H5A | 0.9700 |
O1—C9 | 1.375 (5) | C5—H5B | 0.9700 |
O1—C8 | 1.375 (5) | C6—C7 | 1.363 (7) |
O2—C6 | 1.379 (6) | C7—C8 | 1.396 (6) |
O2—C5 | 1.420 (6) | C7—H7 | 0.9300 |
O3—C4 | 1.372 (6) | C9—C10 | 1.466 (7) |
O3—C5 | 1.427 (5) | C10—H10A | 0.9600 |
C1—C9 | 1.366 (6) | C10—H10B | 0.9600 |
C1—C2 | 1.439 (6) | C10—H10C | 0.9600 |
C2—C8 | 1.397 (5) | C11—H11A | 0.9600 |
C2—C3 | 1.412 (6) | C11—H11B | 0.9600 |
C3—C4 | 1.370 (6) | C11—H11C | 0.9600 |
| | | |
O4—S—C1 | 106.5 (2) | C7—C6—O2 | 127.5 (4) |
O4—S—C11 | 105.6 (2) | C7—C6—C4 | 123.6 (4) |
C1—S—C11 | 98.6 (2) | O2—C6—C4 | 108.9 (4) |
C9—O1—C8 | 107.4 (3) | C6—C7—C8 | 113.1 (4) |
C6—O2—C5 | 106.7 (3) | C6—C7—H7 | 123.4 |
C4—O3—C5 | 106.3 (3) | C8—C7—H7 | 123.4 |
C9—C1—C2 | 108.3 (4) | O1—C8—C7 | 124.6 (4) |
C9—C1—S | 123.6 (4) | O1—C8—C2 | 110.4 (4) |
C2—C1—S | 127.8 (3) | C7—C8—C2 | 125.0 (4) |
C8—C2—C3 | 120.0 (4) | C1—C9—O1 | 109.4 (4) |
C8—C2—C1 | 104.5 (4) | C1—C9—C10 | 133.5 (4) |
C3—C2—C1 | 135.5 (4) | O1—C9—C10 | 117.1 (4) |
C4—C3—C2 | 114.9 (4) | C9—C10—H10A | 109.5 |
C4—C3—H3 | 122.6 | C9—C10—H10B | 109.5 |
C2—C3—H3 | 122.6 | H10A—C10—H10B | 109.5 |
C3—C4—O3 | 127.0 (4) | C9—C10—H10C | 109.5 |
C3—C4—C6 | 123.3 (4) | H10A—C10—H10C | 109.5 |
O3—C4—C6 | 109.7 (4) | H10B—C10—H10C | 109.5 |
O2—C5—O3 | 108.2 (4) | S—C11—H11A | 109.5 |
O2—C5—H5A | 110.1 | S—C11—H11B | 109.5 |
O3—C5—H5A | 110.1 | H11A—C11—H11B | 109.5 |
O2—C5—H5B | 110.1 | S—C11—H11C | 109.5 |
O3—C5—H5B | 110.1 | H11A—C11—H11C | 109.5 |
H5A—C5—H5B | 108.4 | H11B—C11—H11C | 109.5 |
| | | |
O4—S—C1—C9 | 136.9 (4) | O3—C4—C6—C7 | 179.9 (4) |
C11—S—C1—C9 | −113.8 (4) | C3—C4—C6—O2 | −179.5 (4) |
O4—S—C1—C2 | −35.9 (4) | O3—C4—C6—O2 | 0.0 (5) |
C11—S—C1—C2 | 73.4 (4) | O2—C6—C7—C8 | 179.3 (4) |
C9—C1—C2—C8 | 0.2 (5) | C4—C6—C7—C8 | −0.6 (7) |
S—C1—C2—C8 | 173.9 (3) | C9—O1—C8—C7 | 177.4 (4) |
C9—C1—C2—C3 | −178.5 (5) | C9—O1—C8—C2 | −1.3 (5) |
S—C1—C2—C3 | −4.8 (8) | C6—C7—C8—O1 | −178.6 (4) |
C8—C2—C3—C4 | −1.0 (6) | C6—C7—C8—C2 | −0.1 (7) |
C1—C2—C3—C4 | 177.6 (5) | C3—C2—C8—O1 | 179.6 (4) |
C2—C3—C4—O3 | −179.0 (4) | C1—C2—C8—O1 | 0.6 (5) |
C2—C3—C4—C6 | 0.4 (7) | C3—C2—C8—C7 | 0.9 (7) |
C5—O3—C4—C3 | −177.4 (5) | C1—C2—C8—C7 | −178.0 (4) |
C5—O3—C4—C6 | 3.2 (5) | C2—C1—C9—O1 | −1.0 (5) |
C6—O2—C5—O3 | 5.1 (5) | S—C1—C9—O1 | −175.0 (3) |
C4—O3—C5—O2 | −5.1 (5) | C2—C1—C9—C10 | 177.7 (5) |
C5—O2—C6—C7 | 176.9 (5) | S—C1—C9—C10 | 3.7 (8) |
C5—O2—C6—C4 | −3.2 (5) | C8—O1—C9—C1 | 1.4 (5) |
C3—C4—C6—C7 | 0.5 (8) | C8—O1—C9—C10 | −177.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···Cg1i | 0.96 | 2.93 | 3.841 (6) | 160 |
Symmetry code: (i) x−1, y, z. |