organic compounds
The title compound, C15H11BrO2S, was prepared by oxidation of 5-bromo-3-methylsulfanyl-2-phenyl-1-benzofuran using 3-chloroperbenzoic acid. The crystal structure is stabilized by aromatic π–π stacking and CH2—Hπ interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700685X/bh2081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700685X/bh2081Isup2.hkl |
CCDC reference: 641504
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.021
- wR factor = 0.056
- 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 ....... 0.62 mm PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT431_ALERT_2_C Short Inter HL..A Contact Br .. O1 .. 3.19 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
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-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
5-Bromo-3-methylsulfinyl-2-phenyl-1-benzofuran top
Crystal data top
C15H11BrO2S | Z = 2 |
Mr = 335.21 | F(000) = 336 |
Triclinic, P1 | Dx = 1.686 Mg m−3 |
Hall symbol: -P 1 | Melting point = 448–449 K |
a = 8.1546 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1745 (6) Å | Cell parameters from 4454 reflections |
c = 10.8077 (8) Å | θ = 2.7–28.3° |
α = 91.988 (1)° | µ = 3.26 mm−1 |
β = 94.726 (1)° | T = 173 K |
γ = 112.746 (1)° | Block, colourless |
V = 660.41 (8) Å3 | 0.62 × 0.40 × 0.40 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2690 independent reflections |
Radiation source: fine-focus sealed tube | 2547 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 10.00 pixels mm-1 | θmax = 26.5°, θmin = 1.9° |
φ and ω scans | h = −10→10 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999) | k = −10→10 |
Tmin = 0.230, Tmax = 0.274 | l = −13→13 |
5395 measured 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)] = 0.021 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0307P)2 + 0.234P] where P = (Fo2 + 2Fc2)/3 |
2690 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br | 0.30437 (2) | 0.61010 (2) | 0.523987 (15) | 0.02864 (7) | |
S | −0.28975 (5) | 0.18885 (5) | 0.10006 (4) | 0.02206 (10) | |
O1 | −0.31624 (17) | 0.32448 (17) | 0.18225 (13) | 0.0311 (3) | |
O2 | 0.19654 (15) | 0.34740 (16) | −0.01039 (11) | 0.0218 (2) | |
C1 | 0.2733 (2) | 0.5333 (2) | 0.35242 (15) | 0.0222 (3) | |
C2 | 0.1027 (2) | 0.4332 (2) | 0.29761 (15) | 0.0210 (3) | |
H2 | 0.0035 | 0.4056 | 0.3420 | 0.025* | |
C3 | 0.0862 (2) | 0.3753 (2) | 0.17219 (15) | 0.0194 (3) | |
C4 | −0.0590 (2) | 0.2685 (2) | 0.08098 (15) | 0.0197 (3) | |
C5 | 0.0136 (2) | 0.2563 (2) | −0.02655 (15) | 0.0201 (3) | |
C6 | 0.2395 (2) | 0.4211 (2) | 0.11054 (15) | 0.0203 (3) | |
C7 | 0.4099 (2) | 0.5223 (2) | 0.16444 (16) | 0.0237 (3) | |
H7 | 0.5089 | 0.5508 | 0.1199 | 0.028* | |
C8 | 0.4255 (2) | 0.5792 (2) | 0.28857 (16) | 0.0238 (3) | |
H8 | 0.5373 | 0.6481 | 0.3296 | 0.029* | |
C9 | −0.0587 (2) | 0.1669 (2) | −0.14974 (15) | 0.0205 (3) | |
C10 | −0.2106 (2) | 0.0087 (2) | −0.16563 (17) | 0.0252 (4) | |
H10 | −0.2671 | −0.0411 | −0.0967 | 0.030* | |
C11 | −0.2778 (3) | −0.0747 (2) | −0.28328 (18) | 0.0294 (4) | |
H11 | −0.3796 | −0.1796 | −0.2933 | 0.035* | |
C12 | −0.1933 (3) | −0.0019 (3) | −0.38588 (17) | 0.0311 (4) | |
H12 | −0.2387 | −0.0579 | −0.4649 | 0.037* | |
C13 | −0.0412 (3) | 0.1540 (3) | −0.37140 (17) | 0.0296 (4) | |
H13 | 0.0154 | 0.2017 | −0.4407 | 0.035* | |
C14 | 0.0269 (2) | 0.2394 (2) | −0.25434 (16) | 0.0238 (3) | |
H14 | 0.1289 | 0.3442 | −0.2451 | 0.029* | |
C15 | −0.3001 (3) | 0.0115 (3) | 0.1963 (2) | 0.0362 (4) | |
H15A | −0.2135 | 0.0577 | 0.2677 | 0.054* | |
H15B | −0.2748 | −0.0766 | 0.1496 | 0.054* | |
H15C | −0.4175 | −0.0417 | 0.2229 | 0.054* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.02637 (11) | 0.03803 (12) | 0.01949 (10) | 0.01168 (8) | −0.00169 (7) | −0.00377 (7) |
S | 0.01494 (19) | 0.0234 (2) | 0.0268 (2) | 0.00619 (16) | 0.00323 (16) | 0.00212 (16) |
O1 | 0.0262 (7) | 0.0284 (6) | 0.0408 (8) | 0.0117 (5) | 0.0117 (6) | 0.0003 (6) |
O2 | 0.0170 (6) | 0.0268 (6) | 0.0192 (6) | 0.0057 (5) | 0.0033 (5) | −0.0001 (4) |
C1 | 0.0248 (8) | 0.0246 (8) | 0.0178 (8) | 0.0107 (7) | 0.0006 (6) | −0.0003 (6) |
C2 | 0.0185 (8) | 0.0248 (8) | 0.0206 (8) | 0.0094 (6) | 0.0028 (6) | 0.0016 (6) |
C3 | 0.0164 (7) | 0.0197 (7) | 0.0217 (8) | 0.0067 (6) | 0.0023 (6) | 0.0023 (6) |
C4 | 0.0159 (7) | 0.0211 (8) | 0.0218 (8) | 0.0066 (6) | 0.0024 (6) | 0.0020 (6) |
C5 | 0.0167 (8) | 0.0195 (7) | 0.0230 (8) | 0.0057 (6) | 0.0018 (6) | 0.0030 (6) |
C6 | 0.0203 (8) | 0.0220 (8) | 0.0189 (8) | 0.0085 (6) | 0.0023 (6) | 0.0012 (6) |
C7 | 0.0178 (8) | 0.0265 (8) | 0.0252 (8) | 0.0062 (7) | 0.0054 (7) | 0.0036 (7) |
C8 | 0.0188 (8) | 0.0249 (8) | 0.0246 (8) | 0.0059 (6) | −0.0013 (7) | 0.0007 (6) |
C9 | 0.0208 (8) | 0.0213 (8) | 0.0211 (8) | 0.0101 (6) | 0.0017 (6) | 0.0003 (6) |
C10 | 0.0249 (9) | 0.0248 (8) | 0.0247 (9) | 0.0083 (7) | 0.0040 (7) | 0.0011 (7) |
C11 | 0.0279 (9) | 0.0249 (9) | 0.0306 (9) | 0.0067 (7) | −0.0015 (8) | −0.0050 (7) |
C12 | 0.0361 (10) | 0.0338 (10) | 0.0232 (9) | 0.0152 (8) | −0.0025 (8) | −0.0070 (7) |
C13 | 0.0357 (10) | 0.0347 (10) | 0.0217 (8) | 0.0169 (8) | 0.0054 (7) | 0.0031 (7) |
C14 | 0.0234 (8) | 0.0248 (8) | 0.0245 (8) | 0.0105 (7) | 0.0035 (7) | 0.0021 (7) |
C15 | 0.0309 (10) | 0.0297 (10) | 0.0513 (12) | 0.0120 (8) | 0.0166 (9) | 0.0160 (9) |
Geometric parameters (Å, º) top
Br—C1 | 1.901 (2) | C7—H7 | 0.9300 |
S—O1 | 1.488 (1) | C8—H8 | 0.9300 |
S—C4 | 1.770 (2) | C9—C10 | 1.395 (2) |
S—C15 | 1.793 (2) | C9—C14 | 1.405 (2) |
O2—C5 | 1.378 (2) | C10—C11 | 1.385 (3) |
O2—C6 | 1.379 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.381 (2) | C11—C12 | 1.383 (3) |
C1—C8 | 1.399 (2) | C11—H11 | 0.9300 |
C2—C3 | 1.399 (2) | C12—C13 | 1.385 (3) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C6 | 1.393 (2) | C13—C14 | 1.385 (3) |
C3—C4 | 1.443 (2) | C13—H13 | 0.9300 |
C4—C5 | 1.364 (2) | C14—H14 | 0.9300 |
C5—C9 | 1.458 (2) | C15—H15A | 0.9600 |
C6—C7 | 1.378 (2) | C15—H15B | 0.9600 |
C7—C8 | 1.384 (2) | C15—H15C | 0.9600 |
O1—S—C4 | 107.08 (8) | C7—C8—H8 | 119.9 |
O1—S—C15 | 105.69 (9) | C1—C8—H8 | 119.9 |
C4—S—C15 | 97.91 (8) | C10—C9—C14 | 119.21 (16) |
C5—O2—C6 | 106.77 (12) | C10—C9—C5 | 121.12 (15) |
C2—C1—C8 | 123.32 (15) | C14—C9—C5 | 119.67 (15) |
C2—C1—Br | 118.60 (12) | C11—C10—C9 | 120.47 (17) |
C8—C1—Br | 118.08 (13) | C11—C10—H10 | 119.8 |
C1—C2—C3 | 116.78 (15) | C9—C10—H10 | 119.8 |
C1—C2—H2 | 121.6 | C12—C11—C10 | 119.95 (17) |
C3—C2—H2 | 121.6 | C12—C11—H11 | 120.0 |
C6—C3—C2 | 119.02 (15) | C10—C11—H11 | 120.0 |
C6—C3—C4 | 105.21 (14) | C11—C12—C13 | 120.22 (17) |
C2—C3—C4 | 135.76 (15) | C11—C12—H12 | 119.9 |
C5—C4—C3 | 107.20 (14) | C13—C12—H12 | 119.9 |
C5—C4—S | 126.24 (13) | C12—C13—C14 | 120.43 (17) |
C3—C4—S | 126.24 (12) | C12—C13—H13 | 119.8 |
C4—C5—O2 | 110.47 (14) | C14—C13—H13 | 119.8 |
C4—C5—C9 | 134.34 (15) | C13—C14—C9 | 119.71 (16) |
O2—C5—C9 | 115.17 (14) | C13—C14—H14 | 120.1 |
C7—C6—O2 | 125.19 (15) | C9—C14—H14 | 120.1 |
C7—C6—C3 | 124.45 (15) | S—C15—H15A | 109.5 |
O2—C6—C3 | 110.34 (14) | S—C15—H15B | 109.5 |
C6—C7—C8 | 116.29 (15) | H15A—C15—H15B | 109.5 |
C6—C7—H7 | 121.9 | S—C15—H15C | 109.5 |
C8—C7—H7 | 121.9 | H15A—C15—H15C | 109.5 |
C7—C8—C1 | 120.13 (16) | H15B—C15—H15C | 109.5 |
C8—C1—C2—C3 | 0.8 (2) | C4—C3—C6—C7 | −179.38 (16) |
Br—C1—C2—C3 | −178.31 (12) | C2—C3—C6—O2 | 178.12 (14) |
C1—C2—C3—C6 | −0.2 (2) | C4—C3—C6—O2 | −0.80 (18) |
C1—C2—C3—C4 | 178.34 (17) | O2—C6—C7—C8 | −177.89 (15) |
C6—C3—C4—C5 | 0.25 (18) | C3—C6—C7—C8 | 0.5 (3) |
C2—C3—C4—C5 | −178.40 (18) | C6—C7—C8—C1 | 0.1 (2) |
C6—C3—C4—S | −173.54 (12) | C2—C1—C8—C7 | −0.7 (3) |
C2—C3—C4—S | 7.8 (3) | Br—C1—C8—C7 | 178.32 (13) |
O1—S—C4—C5 | −139.86 (15) | C4—C5—C9—C10 | −30.3 (3) |
C15—S—C4—C5 | 110.96 (16) | O2—C5—C9—C10 | 148.05 (15) |
O1—S—C4—C3 | 32.77 (16) | C4—C5—C9—C14 | 150.65 (18) |
C15—S—C4—C3 | −76.40 (16) | O2—C5—C9—C14 | −31.0 (2) |
C3—C4—C5—O2 | 0.39 (18) | C14—C9—C10—C11 | −0.9 (3) |
S—C4—C5—O2 | 174.18 (11) | C5—C9—C10—C11 | 180.00 (16) |
C3—C4—C5—C9 | 178.76 (17) | C9—C10—C11—C12 | 0.5 (3) |
S—C4—C5—C9 | −7.5 (3) | C10—C11—C12—C13 | 0.2 (3) |
C6—O2—C5—C4 | −0.88 (17) | C11—C12—C13—C14 | −0.5 (3) |
C6—O2—C5—C9 | −179.59 (13) | C12—C13—C14—C9 | 0.1 (3) |
C5—O2—C6—C7 | 179.61 (16) | C10—C9—C14—C13 | 0.6 (3) |
C5—O2—C6—C3 | 1.05 (17) | C5—C9—C14—C13 | 179.68 (16) |
C2—C3—C6—C7 | −0.5 (3) |