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ISSN: 2056-9890

3-(4-Fluoro­phenyl­sulfon­yl)-5-iodo-2,7-di­methyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 6 December 2011; accepted 7 December 2011; online 10 December 2011)

In the title compound, C16H12FIO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, and by an I⋯I contact [3.7764 (3) Å]. The crystal structure also exhibits a weak C—I⋯π [3.901 (3) Å] inter­action and a slipped ππ inter­action between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.845 (3), inter­planar distance = 3.555 (3) and slippage = 1.465 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For related structures, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o930.], 2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1082.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12FIO3S

  • Mr = 430.22

  • Triclinic, [P \overline 1]

  • a = 7.5839 (2) Å

  • b = 10.2443 (3) Å

  • c = 10.4651 (3) Å

  • α = 79.424 (1)°

  • β = 75.652 (1)°

  • γ = 80.361 (1)°

  • V = 767.94 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.24 mm−1

  • T = 173 K

  • 0.32 × 0.30 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.534, Tmax = 0.689

  • 13962 measured reflections

  • 3785 independent reflections

  • 3585 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.022

  • wR(F2) = 0.057

  • S = 1.08

  • 3785 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O3i 0.95 2.54 3.253 (2) 132
C15—H15⋯O2ii 0.95 2.52 3.294 (3) 139
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Recently, benzofuran derivatives have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of benzofuran derivatives containing either 3-phenylsulfonyl (Choi et al., 2008) or 3-(4-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 72.31 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (see Table 1), and by an I···I contact at 3.7764 (3) Å. The crystal packing (Fig. 3) is further stabilized by a weak C—I···π interaction between the iodine and the benzene ring of an adjacent molecule, with a C4—I1···Cg2v [3.901 (3) Å] (Cg2 is the centroid of the C2···C7 benzene ring). The crystal packing (Fig. 3) is also exhibits a weak slipped ππ interaction between the furan and benzene rings of adjacent molecules, with a Cg1···Cg2iv distance of 3.845 (3) Å and an interplanar distance of 3.555 (3) Å resulting in a slippage of 1.465 (3) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2008, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 430–431 K; Rf = 0.53 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å fo the aryl and 0.98 Å for the methylene H atoms. Uiso(H) =1.2Ueq(C) for the aryl and 1.5Ueq(C) for the methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and I···I interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity [Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y, -z+2; (iii) -x+1, -y, -z+1].
[Figure 3] Fig. 3. A view of the C—I···π and ππ interactions (dotted lines) in the crystal structure of the title compound. H atoms were omitted for clarity [Symmetry codes: (iv) -x, -y+1, -z+1; (v) -x+1, -y+1, -z+1].
3-(4-Fluorophenylsulfonyl)-5-iodo-2,7-dimethyl-1-benzofuran top
Crystal data top
C16H12FIO3SZ = 2
Mr = 430.22F(000) = 420
Triclinic, P1Dx = 1.861 Mg m3
Hall symbol: -P 1Melting point: 430 K
a = 7.5839 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2443 (3) ÅCell parameters from 9929 reflections
c = 10.4651 (3) Åθ = 2.7–28.3°
α = 79.424 (1)°µ = 2.24 mm1
β = 75.652 (1)°T = 173 K
γ = 80.361 (1)°Block, colourless
V = 767.94 (4) Å30.32 × 0.30 × 0.18 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3785 independent reflections
Radiation source: rotating anode3585 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
ϕ and ω scansh = 910
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.534, Tmax = 0.689l = 1313
13962 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)] = 0.022Hydrogen site location: difference Fourier map
wR(F2) = 0.057H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.028P)2 + 0.3904P]
where P = (Fo2 + 2Fc2)/3
3785 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.72 e Å3
0 constraints
Crystal data top
C16H12FIO3Sγ = 80.361 (1)°
Mr = 430.22V = 767.94 (4) Å3
Triclinic, P1Z = 2
a = 7.5839 (2) ÅMo Kα radiation
b = 10.2443 (3) ŵ = 2.24 mm1
c = 10.4651 (3) ÅT = 173 K
α = 79.424 (1)°0.32 × 0.30 × 0.18 mm
β = 75.652 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3785 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3585 reflections with I > 2σ(I)
Tmin = 0.534, Tmax = 0.689Rint = 0.028
13962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.057H-atom parameters constrained
S = 1.08Δρmax = 0.47 e Å3
3785 reflectionsΔρmin = 0.72 e Å3
201 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.458085 (17)0.514608 (14)0.182660 (11)0.03682 (6)
S10.09268 (6)0.13784 (4)0.70600 (4)0.02423 (9)
F10.7392 (2)0.17671 (16)0.86383 (18)0.0602 (4)
O10.07637 (18)0.50285 (12)0.77645 (12)0.0243 (2)
O20.1076 (2)0.12200 (14)0.56993 (14)0.0337 (3)
O30.06489 (19)0.09921 (14)0.80627 (15)0.0332 (3)
C10.1071 (2)0.30519 (17)0.70547 (17)0.0227 (3)
C20.1812 (2)0.39985 (16)0.59204 (17)0.0219 (3)
C30.2651 (2)0.39515 (18)0.45767 (17)0.0242 (3)
H30.28280.31540.41950.029*
C40.3210 (2)0.51397 (19)0.38343 (17)0.0259 (3)
C50.2946 (3)0.63304 (18)0.43641 (19)0.0281 (4)
H50.33450.71140.38020.034*
C60.2110 (3)0.63949 (17)0.56963 (19)0.0261 (3)
C70.1583 (2)0.51938 (17)0.64268 (17)0.0226 (3)
C80.0489 (2)0.37130 (17)0.81325 (18)0.0242 (3)
C90.1834 (3)0.76435 (19)0.6319 (2)0.0358 (4)
H9A0.27860.75970.68170.054*
H9B0.06230.77230.69280.054*
H9C0.19140.84250.56200.054*
C100.0272 (3)0.3303 (2)0.95636 (18)0.0326 (4)
H10A0.05230.23730.97120.049*
H10B0.14140.38850.98530.049*
H10C0.06160.33791.00770.049*
C110.2897 (2)0.04748 (16)0.75598 (17)0.0239 (3)
C120.2733 (3)0.02336 (19)0.88349 (19)0.0318 (4)
H120.15800.01910.94530.038*
C130.4256 (3)0.1004 (2)0.9203 (2)0.0391 (5)
H130.41690.15141.00670.047*
C140.5908 (3)0.1011 (2)0.8280 (2)0.0380 (4)
C150.6120 (3)0.0298 (2)0.7025 (2)0.0368 (4)
H150.72880.03180.64250.044*
C160.4587 (3)0.0453 (2)0.66519 (19)0.0304 (4)
H160.46860.09510.57830.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03090 (8)0.05323 (10)0.02085 (7)0.00336 (6)0.00149 (5)0.00069 (5)
S10.0273 (2)0.02141 (18)0.0241 (2)0.00622 (16)0.00472 (16)0.00224 (15)
F10.0409 (8)0.0588 (9)0.0736 (11)0.0116 (7)0.0215 (7)0.0040 (8)
O10.0276 (6)0.0228 (6)0.0215 (6)0.0025 (5)0.0034 (5)0.0042 (4)
O20.0468 (8)0.0291 (7)0.0292 (7)0.0055 (6)0.0134 (6)0.0071 (5)
O30.0276 (7)0.0322 (7)0.0373 (8)0.0115 (5)0.0017 (6)0.0002 (6)
C10.0243 (8)0.0213 (7)0.0219 (8)0.0038 (6)0.0043 (6)0.0018 (6)
C20.0204 (8)0.0220 (7)0.0225 (8)0.0020 (6)0.0046 (6)0.0024 (6)
C30.0237 (8)0.0260 (8)0.0221 (8)0.0020 (6)0.0043 (6)0.0032 (6)
C40.0227 (8)0.0328 (9)0.0199 (8)0.0028 (7)0.0035 (6)0.0002 (7)
C50.0273 (9)0.0271 (8)0.0282 (9)0.0061 (7)0.0073 (7)0.0043 (7)
C60.0264 (9)0.0223 (8)0.0299 (9)0.0037 (6)0.0080 (7)0.0016 (7)
C70.0215 (8)0.0235 (8)0.0220 (8)0.0017 (6)0.0040 (6)0.0033 (6)
C80.0238 (8)0.0247 (8)0.0239 (8)0.0036 (6)0.0054 (6)0.0026 (6)
C90.0468 (12)0.0237 (8)0.0384 (11)0.0065 (8)0.0107 (9)0.0050 (8)
C100.0386 (11)0.0356 (10)0.0208 (8)0.0062 (8)0.0015 (7)0.0028 (7)
C110.0271 (9)0.0191 (7)0.0240 (8)0.0036 (6)0.0033 (6)0.0026 (6)
C120.0320 (10)0.0310 (9)0.0272 (9)0.0056 (7)0.0011 (7)0.0026 (7)
C130.0424 (12)0.0353 (10)0.0342 (10)0.0031 (9)0.0099 (9)0.0088 (8)
C140.0342 (11)0.0324 (10)0.0470 (12)0.0029 (8)0.0133 (9)0.0057 (9)
C150.0282 (10)0.0413 (11)0.0382 (11)0.0025 (8)0.0010 (8)0.0100 (9)
C160.0308 (10)0.0329 (9)0.0252 (8)0.0066 (7)0.0006 (7)0.0037 (7)
Geometric parameters (Å, º) top
I1—C42.1000 (17)C6—C91.501 (3)
I1—I1i3.7764 (3)C8—C101.475 (2)
S1—O21.4372 (14)C9—H9A0.9800
S1—O31.4388 (14)C9—H9B0.9800
S1—C11.7349 (17)C9—H9C0.9800
S1—C111.7633 (19)C10—H10A0.9800
F1—C141.348 (3)C10—H10B0.9800
O1—C81.368 (2)C10—H10C0.9800
O1—C71.375 (2)C11—C121.384 (3)
C1—C81.364 (2)C11—C161.393 (2)
C1—C21.447 (2)C12—C131.382 (3)
C2—C71.390 (2)C12—H120.9500
C2—C31.398 (2)C13—C141.379 (3)
C3—C41.388 (2)C13—H130.9500
C3—H30.9500C14—C151.367 (3)
C4—C51.395 (3)C15—C161.382 (3)
C5—C61.390 (3)C15—H150.9500
C5—H50.9500C16—H160.9500
C6—C71.388 (2)
C4—I1—I1i159.65 (5)O1—C8—C10115.71 (15)
O2—S1—O3119.47 (9)C6—C9—H9A109.5
O2—S1—C1106.66 (8)C6—C9—H9B109.5
O3—S1—C1108.80 (8)H9A—C9—H9B109.5
O2—S1—C11107.68 (9)C6—C9—H9C109.5
O3—S1—C11107.59 (9)H9A—C9—H9C109.5
C1—S1—C11105.89 (8)H9B—C9—H9C109.5
C8—O1—C7107.10 (13)C8—C10—H10A109.5
C8—C1—C2107.64 (15)C8—C10—H10B109.5
C8—C1—S1125.62 (13)H10A—C10—H10B109.5
C2—C1—S1126.74 (13)C8—C10—H10C109.5
C7—C2—C3119.58 (16)H10A—C10—H10C109.5
C7—C2—C1104.40 (14)H10B—C10—H10C109.5
C3—C2—C1136.01 (16)C12—C11—C16120.97 (18)
C4—C3—C2116.04 (16)C12—C11—S1119.54 (14)
C4—C3—H3122.0C16—C11—S1119.47 (14)
C2—C3—H3122.0C13—C12—C11119.60 (18)
C3—C4—C5123.23 (16)C13—C12—H12120.2
C3—C4—I1118.75 (13)C11—C12—H12120.2
C5—C4—I1118.01 (13)C14—C13—C12118.06 (19)
C6—C5—C4121.44 (16)C14—C13—H13121.0
C6—C5—H5119.3C12—C13—H13121.0
C4—C5—H5119.3F1—C14—C15118.3 (2)
C7—C6—C5114.51 (16)F1—C14—C13118.0 (2)
C7—C6—C9122.07 (17)C15—C14—C13123.6 (2)
C5—C6—C9123.40 (17)C14—C15—C16118.16 (19)
O1—C7—C6124.09 (15)C14—C15—H15120.9
O1—C7—C2110.72 (14)C16—C15—H15120.9
C6—C7—C2125.19 (16)C15—C16—C11119.55 (19)
C1—C8—O1110.13 (15)C15—C16—H16120.2
C1—C8—C10134.10 (16)C11—C16—H16120.2
O2—S1—C1—C8160.36 (16)C3—C2—C7—O1178.98 (15)
O3—S1—C1—C830.24 (19)C1—C2—C7—O10.15 (19)
C11—S1—C1—C885.14 (18)C3—C2—C7—C60.7 (3)
O2—S1—C1—C219.34 (19)C1—C2—C7—C6179.55 (17)
O3—S1—C1—C2149.46 (16)C2—C1—C8—O11.5 (2)
C11—S1—C1—C295.16 (17)S1—C1—C8—O1178.27 (13)
C8—C1—C2—C70.8 (2)C2—C1—C8—C10175.6 (2)
S1—C1—C2—C7178.95 (14)S1—C1—C8—C104.7 (3)
C8—C1—C2—C3177.7 (2)C7—O1—C8—C11.56 (19)
S1—C1—C2—C32.5 (3)C7—O1—C8—C10176.10 (16)
C7—C2—C3—C40.2 (3)O2—S1—C11—C12140.80 (15)
C1—C2—C3—C4178.18 (19)O3—S1—C11—C1210.81 (17)
C2—C3—C4—C50.9 (3)C1—S1—C11—C12105.39 (16)
C2—C3—C4—I1177.53 (12)O2—S1—C11—C1637.34 (17)
I1i—I1—C4—C363.4 (2)O3—S1—C11—C16167.33 (14)
I1i—I1—C4—C5118.06 (16)C1—S1—C11—C1676.46 (16)
C3—C4—C5—C60.8 (3)C16—C11—C12—C131.8 (3)
I1—C4—C5—C6177.66 (14)S1—C11—C12—C13176.32 (16)
C4—C5—C6—C70.1 (3)C11—C12—C13—C141.4 (3)
C4—C5—C6—C9178.53 (19)C12—C13—C14—F1179.7 (2)
C8—O1—C7—C6178.67 (17)C12—C13—C14—C150.1 (4)
C8—O1—C7—C21.04 (19)F1—C14—C15—C16178.6 (2)
C5—C6—C7—O1178.82 (16)C13—C14—C15—C161.2 (3)
C9—C6—C7—O10.4 (3)C14—C15—C16—C110.8 (3)
C5—C6—C7—C20.8 (3)C12—C11—C16—C150.7 (3)
C9—C6—C7—C2179.31 (18)S1—C11—C16—C15177.42 (15)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O3ii0.952.543.253 (2)132
C15—H15···O2iii0.952.523.294 (3)139
Symmetry codes: (ii) x, y, z+2; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC16H12FIO3S
Mr430.22
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.5839 (2), 10.2443 (3), 10.4651 (3)
α, β, γ (°)79.424 (1), 75.652 (1), 80.361 (1)
V3)767.94 (4)
Z2
Radiation typeMo Kα
µ (mm1)2.24
Crystal size (mm)0.32 × 0.30 × 0.18
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.534, 0.689
No. of measured, independent and
observed [I > 2σ(I)] reflections
13962, 3785, 3585
Rint0.028
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.057, 1.08
No. of reflections3785
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.72

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O3i0.952.543.253 (2)132.4
C15—H15···O2ii0.952.523.294 (3)139.0
Symmetry codes: (i) x, y, z+2; (ii) x+1, y, z+1.
 

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