organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-(4-Fluoro­phen­yl)-5-iodo-3-iso­propyl­sulfonyl-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 15 October 2012; accepted 17 October 2012; online 20 October 2012)

There are two symmetry-independent mol­ecules, A and B, in the asymmetric unit of the title compound, C17H14FIO3S. The dihedral angle formed by the 4-fluoro­phenyl ring and the mean plane [r.m.s. deviation = 0.013 (2) Å in mol­ecule A and 0.016 (2) Å in mol­ecule B] of the benzofuran fragment is 57.71 (7)° in mol­ecule A and 44.95 (7)° in mol­ecule B. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and I⋯O contacts [I⋯O = 3.3646 (15) and 3.2354 (14) Å], forming a three--dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1043.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14FIO3S

  • Mr = 444.24

  • Triclinic, [P \overline 1]

  • a = 11.7419 (2) Å

  • b = 12.8226 (2) Å

  • c = 12.8474 (2) Å

  • α = 66.576 (1)°

  • β = 82.703 (1)°

  • γ = 67.769 (1)°

  • V = 1642.36 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.10 mm−1

  • T = 173 K

  • 0.31 × 0.22 × 0.22 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 = 0.594, Tmax = 0.746

  • 30779 measured reflections

  • 8149 independent reflections

  • 7224 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.060

  • S = 1.01

  • 8149 reflections

  • 419 parameters

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.88 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O1i 0.95 2.56 3.418 (2) 150
C15—H15⋯O2ii 1.00 2.52 3.520 (3) 177
C30—H30⋯O2iii 0.95 2.58 3.463 (3) 155
C31—H31⋯O3iii 0.95 2.58 3.260 (2) 129
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+1, -z+1; (iii) x-1, y, z.

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

As a part of our ongoing study of 2-(4-fluorophenyl)-5-iodo-1-benzofuran derivatives containing ethylsulfinyl (Choi et al., 2010a) and isopropylsulfinyl (Choi et al., 2010b) substituents in 3-position, we report herein the crystal structure of the title compound which crystallizes with two symmetrically independent molecules, A and B, in the asymmetric unit.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (2)and 0.016 (2) Å, for A and B, respectively, from the least-squares plane defined by its nine constituent atoms. The dihedral angles between the 4-fluorophenyl ring and the mean plane of the benzofuran fragment are 57.71 (7)° in molecule A and 44.95 (7)° in molecule B, respectively. In the crystal packing (Fig. 2), molecules are linked by weak C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also features I···O halogen-bondings between the iodine and the oxygen of the OSO unit [I1···O2iv = 3.3646 (15) Å , C4—I1···O2iv = 152.77 (6)° & I2···O3v = 3.2354 (14) Å, C21—I2···O3v = 170.66 (6)°] (Politzer et al., 2007).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-isopropylsulfanyl-1-benzofuran (330 mg, 0.8 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 72%, m.p. 422–423 K; Rf = 0.65 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine, and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

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 the atom numbering scheme. Displacement ellipsoids are drawn 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 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 + 2, - z; (ii) - x + 2, - y + 1, - z + 1; (iii) x - 1, y, z; (vi) x + 1, y, z.]
[Figure 3] Fig. 3. A view of the I···O interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (iv) - x + 1, - y + 1, - z + 1; (v) - x + 2, - y + 1, - z.]
2-(4-Fluorophenyl)-5-iodo-3-isopropylsulfonyl-1-benzofuran top
Crystal data top
C17H14FIO3SZ = 4
Mr = 444.24F(000) = 872
Triclinic, P1Dx = 1.797 Mg m3
Hall symbol: -P 1Melting point: 422.5 K
a = 11.7419 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.8226 (2) ÅCell parameters from 9874 reflections
c = 12.8474 (2) Åθ = 2.5–28.3°
α = 66.576 (1)°µ = 2.10 mm1
β = 82.703 (1)°T = 173 K
γ = 67.769 (1)°Block, colourless
V = 1642.36 (5) Å30.31 × 0.22 × 0.22 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
8149 independent reflections
Radiation source: rotating anode7224 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.031
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.7°
ϕ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1716
Tmin = 0.594, Tmax = 0.746l = 1717
30779 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)] = 0.025Hydrogen site location: difference Fourier map
wR(F2) = 0.060H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0258P)2 + 0.967P]
where P = (Fo2 + 2Fc2)/3
8149 reflections(Δ/σ)max = 0.001
419 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.88 e Å3
Crystal data top
C17H14FIO3Sγ = 67.769 (1)°
Mr = 444.24V = 1642.36 (5) Å3
Triclinic, P1Z = 4
a = 11.7419 (2) ÅMo Kα radiation
b = 12.8226 (2) ŵ = 2.10 mm1
c = 12.8474 (2) ÅT = 173 K
α = 66.576 (1)°0.31 × 0.22 × 0.22 mm
β = 82.703 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
8149 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7224 reflections with I > 2σ(I)
Tmin = 0.594, Tmax = 0.746Rint = 0.031
30779 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.01Δρmax = 0.65 e Å3
8149 reflectionsΔρmin = 0.88 e Å3
419 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
I10.326089 (13)0.662386 (14)0.466164 (12)0.03553 (5)
I20.737096 (13)0.416299 (14)0.189163 (12)0.03660 (5)
S10.88239 (4)0.60922 (4)0.32898 (4)0.02482 (10)
S20.54126 (4)0.09203 (4)0.24522 (4)0.02417 (10)
F11.12323 (18)0.8849 (3)0.18380 (15)0.0963 (8)
F20.06003 (14)0.13892 (15)0.42793 (13)0.0525 (4)
O10.64958 (12)0.85328 (12)0.07633 (11)0.0260 (3)
O20.84377 (14)0.51275 (13)0.40782 (13)0.0352 (3)
O30.99193 (13)0.57644 (13)0.26654 (13)0.0328 (3)
O40.26036 (12)0.35894 (13)0.04663 (12)0.0274 (3)
O50.64518 (14)0.04309 (14)0.18388 (13)0.0350 (3)
O60.48419 (14)0.01133 (14)0.32324 (13)0.0342 (3)
C10.75915 (17)0.70959 (17)0.23334 (16)0.0230 (4)
C20.62962 (17)0.73192 (16)0.25781 (16)0.0221 (4)
C30.56186 (18)0.68568 (17)0.35032 (17)0.0249 (4)
H30.60080.62550.42050.030*
C40.43510 (18)0.73193 (17)0.33472 (17)0.0253 (4)
C50.37556 (18)0.82104 (18)0.23277 (18)0.0280 (4)
H50.28840.84960.22600.034*
C60.44196 (18)0.86794 (18)0.14196 (17)0.0276 (4)
H60.40300.92920.07220.033*
C70.56748 (17)0.82128 (17)0.15782 (16)0.0236 (4)
C80.76507 (18)0.78429 (18)0.12401 (16)0.0243 (4)
C90.86352 (19)0.8079 (2)0.04658 (16)0.0293 (4)
C100.9528 (2)0.7157 (3)0.01943 (19)0.0390 (5)
H100.95410.63460.05390.047*
C111.0412 (2)0.7437 (3)0.0595 (2)0.0563 (8)
H111.10360.68190.07920.068*
C121.0364 (3)0.8610 (4)0.1074 (2)0.0602 (9)
C130.9495 (3)0.9538 (3)0.0828 (2)0.0540 (8)
H130.94901.03460.11840.065*
C140.8622 (2)0.9275 (2)0.00479 (18)0.0396 (5)
H140.80090.99050.01420.048*
C150.90404 (19)0.6917 (2)0.40407 (17)0.0312 (4)
H150.97390.63480.45980.037*
C160.7904 (2)0.7301 (2)0.47178 (19)0.0403 (5)
H16A0.80570.77050.51630.060*
H16B0.77250.65790.52290.060*
H16C0.71990.78650.41960.060*
C170.9410 (2)0.7973 (2)0.3244 (2)0.0382 (5)
H17A0.87140.85910.27320.057*
H17B1.01080.76790.27980.057*
H17C0.96480.83330.36870.057*
C180.43388 (17)0.21427 (17)0.14277 (16)0.0240 (4)
C190.46896 (18)0.29646 (17)0.04048 (16)0.0242 (4)
C200.57969 (18)0.30585 (19)0.00800 (17)0.0267 (4)
H200.65660.25010.02890.032*
C210.57303 (19)0.3995 (2)0.11194 (17)0.0292 (4)
C220.4612 (2)0.4823 (2)0.16880 (19)0.0336 (5)
H220.46090.54420.24100.040*
C230.3503 (2)0.4745 (2)0.12006 (18)0.0324 (4)
H230.27320.52950.15700.039*
C260.21380 (17)0.22260 (18)0.22001 (16)0.0249 (4)
C240.35885 (18)0.38246 (19)0.01535 (17)0.0266 (4)
C250.30780 (18)0.25643 (17)0.14309 (16)0.0245 (4)
C270.21988 (19)0.10232 (19)0.27135 (18)0.0292 (4)
H270.28790.03950.25820.035*
C280.1273 (2)0.0737 (2)0.34156 (18)0.0327 (4)
H280.13090.00820.37670.039*
C290.0304 (2)0.1664 (2)0.35910 (18)0.0334 (5)
C300.0208 (2)0.2862 (2)0.31029 (19)0.0343 (5)
H300.04740.34810.32460.041*
C310.11328 (19)0.31421 (19)0.23962 (18)0.0295 (4)
H310.10820.39650.20420.035*
C320.58508 (18)0.16381 (18)0.31956 (17)0.0265 (4)
H320.61350.22890.26330.032*
C330.6918 (2)0.0688 (2)0.40173 (19)0.0364 (5)
H33A0.72140.10840.43810.055*
H33B0.75880.03010.36010.055*
H33C0.66380.00690.45980.055*
C340.4752 (2)0.2221 (2)0.3806 (2)0.0370 (5)
H34A0.45040.15850.43990.055*
H34B0.40650.27780.32600.055*
H34C0.49780.26760.41510.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02965 (8)0.04227 (9)0.03667 (8)0.01834 (6)0.01302 (6)0.01549 (7)
I20.03260 (8)0.04483 (9)0.03496 (8)0.02140 (7)0.00914 (6)0.01315 (7)
S10.0195 (2)0.0205 (2)0.0256 (2)0.00292 (17)0.00131 (17)0.00429 (18)
S20.0218 (2)0.0233 (2)0.0259 (2)0.00656 (18)0.00033 (18)0.00919 (18)
F10.0640 (12)0.188 (3)0.0504 (10)0.0825 (15)0.0297 (9)0.0322 (13)
F20.0415 (8)0.0622 (10)0.0547 (9)0.0280 (7)0.0253 (7)0.0214 (8)
O10.0223 (7)0.0286 (7)0.0228 (6)0.0104 (6)0.0003 (5)0.0042 (6)
O20.0287 (8)0.0248 (7)0.0361 (8)0.0061 (6)0.0028 (6)0.0004 (6)
O30.0226 (7)0.0297 (8)0.0369 (8)0.0030 (6)0.0058 (6)0.0110 (6)
O40.0222 (7)0.0291 (7)0.0266 (7)0.0082 (6)0.0005 (5)0.0074 (6)
O50.0281 (8)0.0360 (8)0.0377 (8)0.0025 (6)0.0021 (6)0.0198 (7)
O60.0323 (8)0.0290 (8)0.0377 (8)0.0141 (6)0.0035 (6)0.0051 (6)
C10.0204 (9)0.0228 (9)0.0236 (9)0.0076 (7)0.0031 (7)0.0076 (7)
C20.0194 (9)0.0206 (9)0.0257 (9)0.0057 (7)0.0009 (7)0.0098 (7)
C30.0241 (9)0.0218 (9)0.0256 (9)0.0073 (7)0.0025 (7)0.0074 (7)
C40.0235 (9)0.0237 (9)0.0311 (10)0.0103 (8)0.0070 (8)0.0130 (8)
C50.0203 (9)0.0251 (9)0.0392 (11)0.0077 (8)0.0014 (8)0.0133 (9)
C60.0228 (9)0.0242 (9)0.0308 (10)0.0066 (8)0.0038 (8)0.0057 (8)
C70.0234 (9)0.0228 (9)0.0235 (9)0.0094 (7)0.0017 (7)0.0072 (7)
C80.0225 (9)0.0260 (9)0.0246 (9)0.0088 (8)0.0002 (7)0.0098 (8)
C90.0251 (10)0.0446 (12)0.0204 (9)0.0172 (9)0.0004 (7)0.0101 (9)
C100.0270 (11)0.0594 (15)0.0297 (11)0.0122 (11)0.0021 (9)0.0196 (11)
C110.0269 (12)0.107 (3)0.0342 (13)0.0167 (14)0.0046 (10)0.0342 (15)
C120.0439 (15)0.118 (3)0.0278 (12)0.0539 (18)0.0096 (11)0.0165 (15)
C130.0576 (17)0.084 (2)0.0306 (12)0.0534 (17)0.0019 (12)0.0057 (13)
C140.0442 (13)0.0530 (14)0.0263 (10)0.0310 (12)0.0024 (9)0.0061 (10)
C150.0256 (10)0.0328 (11)0.0277 (10)0.0045 (8)0.0064 (8)0.0077 (9)
C160.0403 (13)0.0501 (14)0.0318 (11)0.0132 (11)0.0049 (10)0.0209 (11)
C170.0351 (12)0.0357 (12)0.0466 (13)0.0147 (10)0.0017 (10)0.0168 (10)
C180.0217 (9)0.0266 (9)0.0241 (9)0.0081 (8)0.0007 (7)0.0107 (8)
C190.0257 (10)0.0256 (9)0.0222 (9)0.0090 (8)0.0003 (7)0.0097 (8)
C200.0239 (10)0.0301 (10)0.0268 (9)0.0098 (8)0.0012 (8)0.0116 (8)
C210.0291 (10)0.0344 (11)0.0280 (10)0.0155 (9)0.0049 (8)0.0130 (9)
C220.0369 (12)0.0332 (11)0.0279 (10)0.0162 (9)0.0020 (9)0.0060 (9)
C230.0299 (11)0.0317 (11)0.0303 (10)0.0092 (9)0.0027 (8)0.0072 (9)
C260.0209 (9)0.0305 (10)0.0252 (9)0.0088 (8)0.0009 (7)0.0129 (8)
C240.0241 (10)0.0310 (10)0.0265 (9)0.0125 (8)0.0030 (8)0.0110 (8)
C250.0261 (10)0.0233 (9)0.0244 (9)0.0075 (8)0.0011 (7)0.0103 (8)
C270.0233 (10)0.0288 (10)0.0364 (11)0.0084 (8)0.0025 (8)0.0147 (9)
C280.0308 (11)0.0320 (11)0.0343 (11)0.0148 (9)0.0009 (9)0.0084 (9)
C290.0275 (10)0.0467 (13)0.0303 (10)0.0199 (10)0.0089 (8)0.0151 (10)
C300.0273 (11)0.0399 (12)0.0364 (11)0.0087 (9)0.0072 (9)0.0201 (10)
C310.0268 (10)0.0286 (10)0.0339 (10)0.0090 (8)0.0027 (8)0.0144 (9)
C320.0272 (10)0.0282 (10)0.0266 (9)0.0119 (8)0.0005 (8)0.0110 (8)
C330.0315 (11)0.0394 (12)0.0364 (11)0.0100 (10)0.0066 (9)0.0129 (10)
C340.0345 (12)0.0410 (12)0.0374 (12)0.0066 (10)0.0015 (9)0.0236 (10)
Geometric parameters (Å, º) top
I1—C42.0982 (19)C15—C171.517 (3)
I1—O2i3.3646 (15)C15—C161.526 (3)
I2—C212.098 (2)C15—H151.0000
I2—O3ii3.2354 (14)C16—H16A0.9800
S1—O21.4399 (15)C16—H16B0.9800
S1—O31.4392 (14)C16—H16C0.9800
S1—C11.7450 (19)C17—H17A0.9800
S1—C151.787 (2)C17—H17B0.9800
S2—O61.4331 (16)C17—H17C0.9800
S2—O51.4400 (15)C18—C251.371 (3)
S2—C181.751 (2)C18—C191.448 (3)
S2—C321.791 (2)C19—C241.389 (3)
F1—C121.357 (3)C19—C201.395 (3)
F2—C291.354 (2)C20—C211.383 (3)
O1—C81.367 (2)C20—H200.9500
O1—C71.377 (2)C21—C221.399 (3)
O4—C251.378 (2)C22—C231.392 (3)
O4—C241.379 (2)C22—H220.9500
C1—C81.361 (3)C23—C241.377 (3)
C1—C21.454 (3)C23—H230.9500
C2—C71.390 (3)C26—C271.392 (3)
C2—C31.398 (3)C26—C311.395 (3)
C3—C41.386 (3)C26—C251.459 (3)
C3—H30.9500C27—C281.385 (3)
C4—C51.396 (3)C27—H270.9500
C5—C61.377 (3)C28—C291.373 (3)
C5—H50.9500C28—H280.9500
C6—C71.372 (3)C29—C301.373 (3)
C6—H60.9500C30—C311.385 (3)
C8—C91.467 (3)C30—H300.9500
C9—C101.384 (3)C31—H310.9500
C9—C141.402 (3)C32—C341.522 (3)
C10—C111.400 (3)C32—C331.526 (3)
C10—H100.9500C32—H321.0000
C11—C121.361 (5)C33—H33A0.9800
C11—H110.9500C33—H33B0.9800
C12—C131.362 (5)C33—H33C0.9800
C13—C141.379 (3)C34—H34A0.9800
C13—H130.9500C34—H34B0.9800
C14—H140.9500C34—H34C0.9800
C4—I1—O2i152.77 (6)H16A—C16—H16C109.5
C21—I2—O3ii170.66 (6)H16B—C16—H16C109.5
O2—S1—O3117.87 (9)C15—C17—H17A109.5
O2—S1—C1106.58 (9)C15—C17—H17B109.5
O3—S1—C1109.02 (9)H17A—C17—H17B109.5
O2—S1—C15108.55 (10)C15—C17—H17C109.5
O3—S1—C15107.76 (10)H17A—C17—H17C109.5
C1—S1—C15106.54 (9)H17B—C17—H17C109.5
O6—S2—O5118.36 (10)C25—C18—C19107.14 (17)
O6—S2—C18110.60 (9)C25—C18—S2129.91 (15)
O5—S2—C18106.18 (9)C19—C18—S2122.84 (14)
O6—S2—C32108.55 (9)C24—C19—C20119.06 (18)
O5—S2—C32108.78 (9)C24—C19—C18105.28 (17)
C18—S2—C32103.33 (9)C20—C19—C18135.65 (18)
C8—O1—C7107.10 (14)C21—C20—C19117.35 (19)
C25—O4—C24107.14 (15)C21—C20—H20121.3
C8—C1—C2107.13 (17)C19—C20—H20121.3
C8—C1—S1126.98 (15)C20—C21—C22122.63 (19)
C2—C1—S1125.85 (14)C20—C21—I2118.79 (15)
C7—C2—C3119.05 (17)C22—C21—I2118.57 (15)
C7—C2—C1104.66 (16)C23—C22—C21120.3 (2)
C3—C2—C1136.28 (18)C23—C22—H22119.9
C4—C3—C2116.79 (18)C21—C22—H22119.9
C4—C3—H3121.6C24—C23—C22116.2 (2)
C2—C3—H3121.6C24—C23—H23121.9
C3—C4—C5122.73 (18)C22—C23—H23121.9
C3—C4—I1119.58 (15)C27—C26—C31119.35 (18)
C5—C4—I1117.65 (14)C27—C26—C25121.84 (17)
C6—C5—C4120.62 (18)C31—C26—C25118.78 (18)
C6—C5—H5119.7C23—C24—O4125.19 (18)
C4—C5—H5119.7C23—C24—C19124.40 (19)
C7—C6—C5116.33 (18)O4—C24—C19110.35 (17)
C7—C6—H6121.8C18—C25—O4110.08 (17)
C5—C6—H6121.8C18—C25—C26136.33 (18)
C6—C7—O1125.00 (17)O4—C25—C26113.56 (16)
C6—C7—C2124.48 (18)C28—C27—C26120.40 (19)
O1—C7—C2110.49 (16)C28—C27—H27119.8
C1—C8—O1110.61 (16)C26—C27—H27119.8
C1—C8—C9135.85 (18)C29—C28—C27118.4 (2)
O1—C8—C9113.54 (16)C29—C28—H28120.8
C10—C9—C14120.1 (2)C27—C28—H28120.8
C10—C9—C8121.0 (2)F2—C29—C30118.2 (2)
C14—C9—C8118.8 (2)F2—C29—C28118.6 (2)
C9—C10—C11119.1 (3)C30—C29—C28123.15 (19)
C9—C10—H10120.5C29—C30—C31118.14 (19)
C11—C10—H10120.5C29—C30—H30120.9
C12—C11—C10118.9 (3)C31—C30—H30120.9
C12—C11—H11120.6C30—C31—C26120.6 (2)
C10—C11—H11120.6C30—C31—H31119.7
C11—C12—F1117.2 (3)C26—C31—H31119.7
C11—C12—C13123.5 (2)C34—C32—C33111.88 (17)
F1—C12—C13119.3 (3)C34—C32—S2110.03 (15)
C12—C13—C14118.3 (3)C33—C32—S2108.70 (14)
C12—C13—H13120.8C34—C32—H32108.7
C14—C13—H13120.8C33—C32—H32108.7
C13—C14—C9120.2 (3)S2—C32—H32108.7
C13—C14—H14119.9C32—C33—H33A109.5
C9—C14—H14119.9C32—C33—H33B109.5
C17—C15—C16113.35 (19)H33A—C33—H33B109.5
C17—C15—S1110.96 (15)C32—C33—H33C109.5
C16—C15—S1110.46 (16)H33A—C33—H33C109.5
C17—C15—H15107.3H33B—C33—H33C109.5
C16—C15—H15107.3C32—C34—H34A109.5
S1—C15—H15107.3C32—C34—H34B109.5
C15—C16—H16A109.5H34A—C34—H34B109.5
C15—C16—H16B109.5C32—C34—H34C109.5
H16A—C16—H16B109.5H34A—C34—H34C109.5
C15—C16—H16C109.5H34B—C34—H34C109.5
O2—S1—C1—C8152.76 (18)O6—S2—C18—C2517.2 (2)
O3—S1—C1—C824.6 (2)O5—S2—C18—C25146.80 (18)
C15—S1—C1—C891.48 (19)C32—S2—C18—C2598.80 (19)
O2—S1—C1—C229.66 (19)O6—S2—C18—C19167.17 (15)
O3—S1—C1—C2157.87 (16)O5—S2—C18—C1937.57 (18)
C15—S1—C1—C286.10 (18)C32—S2—C18—C1976.83 (17)
C8—C1—C2—C70.2 (2)C25—C18—C19—C241.1 (2)
S1—C1—C2—C7177.74 (14)S2—C18—C19—C24177.63 (14)
C8—C1—C2—C3178.5 (2)C25—C18—C19—C20178.6 (2)
S1—C1—C2—C33.6 (3)S2—C18—C19—C202.1 (3)
C7—C2—C3—C41.0 (3)C24—C19—C20—C211.9 (3)
C1—C2—C3—C4177.6 (2)C18—C19—C20—C21178.4 (2)
C2—C3—C4—C50.5 (3)C19—C20—C21—C220.5 (3)
C2—C3—C4—I1177.18 (13)C19—C20—C21—I2179.34 (14)
O2i—I1—C4—C3102.08 (18)O3ii—I2—C21—C2030.8 (5)
O2i—I1—C4—C575.7 (2)O3ii—I2—C21—C22150.3 (3)
C3—C4—C5—C60.4 (3)C20—C21—C22—C231.5 (3)
I1—C4—C5—C6178.08 (15)I2—C21—C22—C23179.71 (16)
C4—C5—C6—C70.7 (3)C21—C22—C23—C240.1 (3)
C5—C6—C7—O1177.68 (18)C22—C23—C24—O4179.66 (19)
C5—C6—C7—C20.1 (3)C22—C23—C24—C192.7 (3)
C8—O1—C7—C6178.10 (19)C25—O4—C24—C23177.04 (19)
C8—O1—C7—C20.0 (2)C25—O4—C24—C190.2 (2)
C3—C2—C7—C60.7 (3)C20—C19—C24—C233.7 (3)
C1—C2—C7—C6178.25 (18)C18—C19—C24—C23176.46 (19)
C3—C2—C7—O1178.81 (16)C20—C19—C24—O4178.95 (16)
C1—C2—C7—O10.2 (2)C18—C19—C24—O40.8 (2)
C2—C1—C8—O10.2 (2)C19—C18—C25—O41.0 (2)
S1—C1—C8—O1177.71 (14)S2—C18—C25—O4177.20 (14)
C2—C1—C8—C9179.6 (2)C19—C18—C25—C26176.7 (2)
S1—C1—C8—C92.4 (3)S2—C18—C25—C260.5 (3)
C7—O1—C8—C10.1 (2)C24—O4—C25—C180.5 (2)
C7—O1—C8—C9179.75 (16)C24—O4—C25—C26177.77 (15)
C1—C8—C9—C1059.0 (3)C27—C26—C25—C1846.5 (3)
O1—C8—C9—C10120.9 (2)C31—C26—C25—C18135.5 (2)
C1—C8—C9—C14124.5 (3)C27—C26—C25—O4135.87 (19)
O1—C8—C9—C1455.7 (2)C31—C26—C25—O442.1 (2)
C14—C9—C10—C110.1 (3)C31—C26—C27—C280.2 (3)
C8—C9—C10—C11176.64 (19)C25—C26—C27—C28178.22 (19)
C9—C10—C11—C120.2 (3)C26—C27—C28—C290.1 (3)
C10—C11—C12—F1179.8 (2)C27—C28—C29—F2179.78 (19)
C10—C11—C12—C130.0 (4)C27—C28—C29—C300.1 (3)
C11—C12—C13—C140.3 (4)F2—C29—C30—C31179.8 (2)
F1—C12—C13—C14179.9 (2)C28—C29—C30—C310.3 (3)
C12—C13—C14—C90.4 (4)C29—C30—C31—C260.7 (3)
C10—C9—C14—C130.2 (3)C27—C26—C31—C300.7 (3)
C8—C9—C14—C13176.4 (2)C25—C26—C31—C30178.72 (19)
O2—S1—C15—C17178.23 (14)O6—S2—C32—C3452.80 (17)
O3—S1—C15—C1753.08 (17)O5—S2—C32—C34177.16 (15)
C1—S1—C15—C1763.79 (17)C18—S2—C32—C3464.64 (16)
O2—S1—C15—C1651.66 (17)O6—S2—C32—C3370.04 (16)
O3—S1—C15—C16179.65 (15)O5—S2—C32—C3360.00 (17)
C1—S1—C15—C1662.77 (17)C18—S2—C32—C33172.52 (15)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1iii0.952.563.418 (2)150
C15—H15···O2iv1.002.523.520 (3)177
C30—H30···O2v0.952.583.463 (3)155
C31—H31···O3v0.952.583.260 (2)129
Symmetry codes: (iii) x+1, y+2, z; (iv) x+2, y+1, z+1; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H14FIO3S
Mr444.24
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.7419 (2), 12.8226 (2), 12.8474 (2)
α, β, γ (°)66.576 (1), 82.703 (1), 67.769 (1)
V3)1642.36 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.10
Crystal size (mm)0.31 × 0.22 × 0.22
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.594, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
30779, 8149, 7224
Rint0.031
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.060, 1.01
No. of reflections8149
No. of parameters419
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.88

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
C6—H6···O1i0.952.563.418 (2)150.1
C15—H15···O2ii1.002.523.520 (3)176.9
C30—H30···O2iii0.952.583.463 (3)155.4
C31—H31···O3iii0.952.583.260 (2)129.2
Symmetry codes: (i) x+1, y+2, z; (ii) x+2, y+1, z+1; (iii) x1, y, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1043.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationPolitzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds