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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—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700685X/bh2081sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700685X/bh2081Isup2.hkl
Contains datablock I

CCDC reference: 641504

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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
C15H11BrO2SZ = 2
Mr = 335.21F(000) = 336
Triclinic, P1Dx = 1.686 Mg m3
Hall symbol: -P 1Melting point = 448–449 K
a = 8.1546 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1745 (6) ÅCell parameters from 4454 reflections
c = 10.8077 (8) Åθ = 2.7–28.3°
α = 91.988 (1)°µ = 3.26 mm1
β = 94.726 (1)°T = 173 K
γ = 112.746 (1)°Block, colourless
V = 660.41 (8) Å30.62 × 0.40 × 0.40 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2690 independent reflections
Radiation source: fine-focus sealed tube2547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 10.00 pixels mm-1θmax = 26.5°, θmin = 1.9°
φ and ω scansh = 1010
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1999)
k = 1010
Tmin = 0.230, Tmax = 0.274l = 1313
5395 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-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 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.37 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br0.30437 (2)0.61010 (2)0.523987 (15)0.02864 (7)
S0.28975 (5)0.18885 (5)0.10006 (4)0.02206 (10)
O10.31624 (17)0.32448 (17)0.18225 (13)0.0311 (3)
O20.19654 (15)0.34740 (16)0.01039 (11)0.0218 (2)
C10.2733 (2)0.5333 (2)0.35242 (15)0.0222 (3)
C20.1027 (2)0.4332 (2)0.29761 (15)0.0210 (3)
H20.00350.40560.34200.025*
C30.0862 (2)0.3753 (2)0.17219 (15)0.0194 (3)
C40.0590 (2)0.2685 (2)0.08098 (15)0.0197 (3)
C50.0136 (2)0.2563 (2)0.02655 (15)0.0201 (3)
C60.2395 (2)0.4211 (2)0.11054 (15)0.0203 (3)
C70.4099 (2)0.5223 (2)0.16444 (16)0.0237 (3)
H70.50890.55080.11990.028*
C80.4255 (2)0.5792 (2)0.28857 (16)0.0238 (3)
H80.53730.64810.32960.029*
C90.0587 (2)0.1669 (2)0.14974 (15)0.0205 (3)
C100.2106 (2)0.0087 (2)0.16563 (17)0.0252 (4)
H100.26710.04110.09670.030*
C110.2778 (3)0.0747 (2)0.28328 (18)0.0294 (4)
H110.37960.17960.29330.035*
C120.1933 (3)0.0019 (3)0.38588 (17)0.0311 (4)
H120.23870.05790.46490.037*
C130.0412 (3)0.1540 (3)0.37140 (17)0.0296 (4)
H130.01540.20170.44070.035*
C140.0269 (2)0.2394 (2)0.25434 (16)0.0238 (3)
H140.12890.34420.24510.029*
C150.3001 (3)0.0115 (3)0.1963 (2)0.0362 (4)
H15A0.21350.05770.26770.054*
H15B0.27480.07660.14960.054*
H15C0.41750.04170.22290.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02637 (11)0.03803 (12)0.01949 (10)0.01168 (8)0.00169 (7)0.00377 (7)
S0.01494 (19)0.0234 (2)0.0268 (2)0.00619 (16)0.00323 (16)0.00212 (16)
O10.0262 (7)0.0284 (6)0.0408 (8)0.0117 (5)0.0117 (6)0.0003 (6)
O20.0170 (6)0.0268 (6)0.0192 (6)0.0057 (5)0.0033 (5)0.0001 (4)
C10.0248 (8)0.0246 (8)0.0178 (8)0.0107 (7)0.0006 (6)0.0003 (6)
C20.0185 (8)0.0248 (8)0.0206 (8)0.0094 (6)0.0028 (6)0.0016 (6)
C30.0164 (7)0.0197 (7)0.0217 (8)0.0067 (6)0.0023 (6)0.0023 (6)
C40.0159 (7)0.0211 (8)0.0218 (8)0.0066 (6)0.0024 (6)0.0020 (6)
C50.0167 (8)0.0195 (7)0.0230 (8)0.0057 (6)0.0018 (6)0.0030 (6)
C60.0203 (8)0.0220 (8)0.0189 (8)0.0085 (6)0.0023 (6)0.0012 (6)
C70.0178 (8)0.0265 (8)0.0252 (8)0.0062 (7)0.0054 (7)0.0036 (7)
C80.0188 (8)0.0249 (8)0.0246 (8)0.0059 (6)0.0013 (7)0.0007 (6)
C90.0208 (8)0.0213 (8)0.0211 (8)0.0101 (6)0.0017 (6)0.0003 (6)
C100.0249 (9)0.0248 (8)0.0247 (9)0.0083 (7)0.0040 (7)0.0011 (7)
C110.0279 (9)0.0249 (9)0.0306 (9)0.0067 (7)0.0015 (8)0.0050 (7)
C120.0361 (10)0.0338 (10)0.0232 (9)0.0152 (8)0.0025 (8)0.0070 (7)
C130.0357 (10)0.0347 (10)0.0217 (8)0.0169 (8)0.0054 (7)0.0031 (7)
C140.0234 (8)0.0248 (8)0.0245 (8)0.0105 (7)0.0035 (7)0.0021 (7)
C150.0309 (10)0.0297 (10)0.0513 (12)0.0120 (8)0.0166 (9)0.0160 (9)
Geometric parameters (Å, º) top
Br—C11.901 (2)C7—H70.9300
S—O11.488 (1)C8—H80.9300
S—C41.770 (2)C9—C101.395 (2)
S—C151.793 (2)C9—C141.405 (2)
O2—C51.378 (2)C10—C111.385 (3)
O2—C61.379 (2)C10—H100.9300
C1—C21.381 (2)C11—C121.383 (3)
C1—C81.399 (2)C11—H110.9300
C2—C31.399 (2)C12—C131.385 (3)
C2—H20.9300C12—H120.9300
C3—C61.393 (2)C13—C141.385 (3)
C3—C41.443 (2)C13—H130.9300
C4—C51.364 (2)C14—H140.9300
C5—C91.458 (2)C15—H15A0.9600
C6—C71.378 (2)C15—H15B0.9600
C7—C81.384 (2)C15—H15C0.9600
O1—S—C4107.08 (8)C7—C8—H8119.9
O1—S—C15105.69 (9)C1—C8—H8119.9
C4—S—C1597.91 (8)C10—C9—C14119.21 (16)
C5—O2—C6106.77 (12)C10—C9—C5121.12 (15)
C2—C1—C8123.32 (15)C14—C9—C5119.67 (15)
C2—C1—Br118.60 (12)C11—C10—C9120.47 (17)
C8—C1—Br118.08 (13)C11—C10—H10119.8
C1—C2—C3116.78 (15)C9—C10—H10119.8
C1—C2—H2121.6C12—C11—C10119.95 (17)
C3—C2—H2121.6C12—C11—H11120.0
C6—C3—C2119.02 (15)C10—C11—H11120.0
C6—C3—C4105.21 (14)C11—C12—C13120.22 (17)
C2—C3—C4135.76 (15)C11—C12—H12119.9
C5—C4—C3107.20 (14)C13—C12—H12119.9
C5—C4—S126.24 (13)C12—C13—C14120.43 (17)
C3—C4—S126.24 (12)C12—C13—H13119.8
C4—C5—O2110.47 (14)C14—C13—H13119.8
C4—C5—C9134.34 (15)C13—C14—C9119.71 (16)
O2—C5—C9115.17 (14)C13—C14—H14120.1
C7—C6—O2125.19 (15)C9—C14—H14120.1
C7—C6—C3124.45 (15)S—C15—H15A109.5
O2—C6—C3110.34 (14)S—C15—H15B109.5
C6—C7—C8116.29 (15)H15A—C15—H15B109.5
C6—C7—H7121.9S—C15—H15C109.5
C8—C7—H7121.9H15A—C15—H15C109.5
C7—C8—C1120.13 (16)H15B—C15—H15C109.5
C8—C1—C2—C30.8 (2)C4—C3—C6—C7179.38 (16)
Br—C1—C2—C3178.31 (12)C2—C3—C6—O2178.12 (14)
C1—C2—C3—C60.2 (2)C4—C3—C6—O20.80 (18)
C1—C2—C3—C4178.34 (17)O2—C6—C7—C8177.89 (15)
C6—C3—C4—C50.25 (18)C3—C6—C7—C80.5 (3)
C2—C3—C4—C5178.40 (18)C6—C7—C8—C10.1 (2)
C6—C3—C4—S173.54 (12)C2—C1—C8—C70.7 (3)
C2—C3—C4—S7.8 (3)Br—C1—C8—C7178.32 (13)
O1—S—C4—C5139.86 (15)C4—C5—C9—C1030.3 (3)
C15—S—C4—C5110.96 (16)O2—C5—C9—C10148.05 (15)
O1—S—C4—C332.77 (16)C4—C5—C9—C14150.65 (18)
C15—S—C4—C376.40 (16)O2—C5—C9—C1431.0 (2)
C3—C4—C5—O20.39 (18)C14—C9—C10—C110.9 (3)
S—C4—C5—O2174.18 (11)C5—C9—C10—C11180.00 (16)
C3—C4—C5—C9178.76 (17)C9—C10—C11—C120.5 (3)
S—C4—C5—C97.5 (3)C10—C11—C12—C130.2 (3)
C6—O2—C5—C40.88 (17)C11—C12—C13—C140.5 (3)
C6—O2—C5—C9179.59 (13)C12—C13—C14—C90.1 (3)
C5—O2—C6—C7179.61 (16)C10—C9—C14—C130.6 (3)
C5—O2—C6—C31.05 (17)C5—C9—C14—C13179.68 (16)
C2—C3—C6—C70.5 (3)
 

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