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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 4| April 2013| Pages o579-o580

1,3-Bis(2,3,5,6-tetra­fluoro-4-iodo­phen­­oxy)-2,2-bis­­[(2,3,5,6-tetra­fluoro-4-iodo­phen­­oxy)meth­yl]propane

aNFMLab, Department of Chemistry, Materials and Chemical Engineering, "G. Natta", Politecnico di Milano, Via Mancinelli, 7, I-20131 Milano, Italy
*Correspondence e-mail: giancarlo.terraneo@polimi.it

(Received 4 February 2013; accepted 19 March 2013; online 23 March 2013)

In the crystal structure of the title compound, C29H8F16I4O4, short I⋯I and I⋯F contacts, which can be understood as halogen bonds (XBs), represent the strongest inter­molecular inter­actions, consistent with the presence of I and F atoms, and the absence of H atoms, at the periphery of the mol­ecule. In addition, ππ stacking inter­actions between tetra­fluoro­iodo­phenyl (TFIP) groups and five short F⋯F inter­actions are present.

Related literature

The title compound is a robust halogen-bonding (XB) donor tecton in supra­molecular chemistry. For background to XB-based crystal engeneering, see: Guido et al. (2004[Guido, E., Metrangolo, P., Pilati, T. & Resnati, G. (2004). Acta Cryst. E60, o788-o790.], 2005[Guido, E., Metrangolo, P., Panzeri, W., Pilati, T., Resnati, G., Ursini, M. & Logothetis, T. A. (2005). J. Fluorine Chem. 126, 197-207.]); Lucassen et al. (2007[Lucassen, A. C. B., Karton, A., Leitus, G., Shimon, L. J. W., Martin, J. M. L. & van der Boom, M. E. (2007). Cryst. Growth Des. 7, 376-392.]); Metrangolo et al. (2007[Metrangolo, P., Meyer, F., Pilati, T., Proserpio, D. & Resnati, G. (2007). Chem. Eur. J. 13, 5765-5772.]). For the synthesis, see: Caronna et al. (2004[Caronna, T., Liantonio, R., Logothetis, T. A., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Am. Chem. Soc. 126, 4500-4501.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C29H8F16I4O4

  • Mr = 1231.95

  • Monoclinic, P 21 /n

  • a = 7.9716 (9) Å

  • b = 20.665 (3) Å

  • c = 20.194 (4) Å

  • β = 92.745 (12)°

  • V = 3322.8 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.88 mm−1

  • T = 90 K

  • 0.34 × 0.06 × 0.04 mm

Data collection
  • Bruker APEX 2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.742, Tmax = 1.000

  • 39668 measured reflections

  • 9728 independent reflections

  • 7975 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.093

  • S = 1.04

  • 9728 reflections

  • 510 parameters

  • 28 restraints

  • All H-atom parameters refined

  • Δρmax = 2.08 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Halogen bonds and C—F⋯F—C and ππ short inter­actions (Å, °)

The distances between the CNTRn of the four TFIP groups showing ππ inter­actions are also reported (CNTRn is the centroid of the benzene group linking the In iodine atom).

C—XY(—C) XY C—XY XY—C
C5—I1⋯I3i 3.7838 (6) 169.59 (11)  
C12—I2⋯F15ii 3.323 (3) 174.72 (11)  
C19—I3⋯F2iii 3.176 (3) 162.73 (11)  
C26—I4⋯F6iv 3.240 (3) 136.47 (11)  
C3—F1⋯(F12—C21)v 2.610 (3) 162.3 (2) 165.1 (3)
C4—F2⋯(F4—C7)v 2.790 (4) 150.2 (2) 149.5 (3)
C17—F9⋯(F11—C20)v 2.771 (4) 151.1 (2) 150.6 (3)
C10—F5⋯(F7—C13)v 2.679 (3) 158.8 (2) 157.2 (3)
C25—F14⋯(F16—C28)vi 2.821 (3) 147.6 (2) 149.2 (3)
CNTR1⋯CNTR4i 3.643 (6)    
C3⋯C27i 3.334 (5)    
C16⋯C11vii 3.317 (5)    
C18⋯C9vii 3.307 (5)    
F9⋯C13vii 3.156 (5)    
CNTR2⋯CNTR3vii 3.648 (6)    
Symmetry codes: (i) [{3\over 2}-x, -{1\over 2}+y, {3\over 2}-z]; (ii) 2-x, 2-y, 2-z; (iii) [-{3\over 2}+x, {3\over 2}-y, -{1\over 2}+z]; (iv) 1-x, 2-y, 2-z; (v) x+1, y, z; (vi) x-1, y, z; (vii) [-{1\over 2}+x, {3\over 2}-y, -{1\over 2}+z].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL2012.

Supporting information


Comment top

The title compound is a flexible molecule synthesized and utilized for halogen bonding (XB) based crystal engeneering (Guido et al., 2004, 2005; Metrangolo et al., 2007). Here we present the structure of the pure compound which is characterized by the presence of I···I and I···F XBs, short F···F contacts and ππ stacking interactions between couples of TFIP pendants. The C—I···F short contancts are particularly interesting as they show C—I···F angles consistent with bona fide XBs. The shortest C—I···F contanct is 3.176 (3) Å (see Table 1) and only few shorter distances are found in the Cambridge Structural Database (Version 5.33; Allen, 2002), the shortest being in WEXVUR (2.962 Å, Lucassen et al., 2007). The molecular symmetry is approximately C2; the torsion angles C0—C1—O1—C2, C0—C8—O2—C9, C0—C15—O3—C16, C0—C22—O4—C23 are 120.9 (3), -162.0 (3), 118.0 (4) and -164.4 (3) °, respectively. Pertinent geometric data are listed in Table 1. The TFIP1 and TFIP3, the phenyl rings bearing I1 and I3, are nearly coplanar and anti-parallel; TFIP2 and TFIP4, the phenyl rings bearing I2 and I4, are not coplanar, but nearly parallel. This conformation favours the formation of π···π interactions between the couples TFIP1/TFIP4 and TFIP2/TFIP3. Supplementary Table A reports the main interactions of the structure. Figure 2 shows the crystal packing.

Related literature top

The title compound is a robust halogen-bonding (XB) donor tecton in supramolecular chemistry. For background to XB-based crystal engeneering, see: Guido et al. (2004, 2005); Lucassen et al. (2007); Metrangolo et al. (2007). For the synthesis, see: Caronna et al. (2004). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The synthesis of the compound was reported by Caronna et al., (2004). Crystals for X-ray analysis were obtained via isothermal evaporation of a chloroform solution.

Refinement top

H atoms were obtained by difference map. They were refined independently with isotropic displacement parameters but restrained to have approximately the same C—H distances.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing viewed along the a axis highlighting the ππ interactions between benzene rings.
1,3-Bis(2,3,5,6-tetrafluoro-4-iodophenoxy)-2,2-bis[(2,3,5,6-tetrafluoro-4-iodophenoxy)methyl]propane top
Crystal data top
C29H8F16I4O4F(000) = 2280
Mr = 1231.95Dx = 2.463 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.9716 (9) ÅCell parameters from 8992 reflections
b = 20.665 (3) Åθ = 2.2–30.0°
c = 20.194 (4) ŵ = 3.88 mm1
β = 92.745 (12)°T = 90 K
V = 3322.8 (9) Å3Neddle, colourless
Z = 40.34 × 0.06 × 0.04 mm
Data collection top
Bruker APEX 2000 CCD area-detector
diffractometer
9728 independent reflections
Radiation source: fine-focus sealed tube7975 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1111
Tmin = 0.742, Tmax = 1.000k = 2925
39668 measured reflectionsl = 2828
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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.093All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0456P)2 + 4.8626P]
where P = (Fo2 + 2Fc2)/3
9728 reflections(Δ/σ)max = 0.004
510 parametersΔρmax = 2.08 e Å3
28 restraintsΔρmin = 0.54 e Å3
Crystal data top
C29H8F16I4O4V = 3322.8 (9) Å3
Mr = 1231.95Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.9716 (9) ŵ = 3.88 mm1
b = 20.665 (3) ÅT = 90 K
c = 20.194 (4) Å0.34 × 0.06 × 0.04 mm
β = 92.745 (12)°
Data collection top
Bruker APEX 2000 CCD area-detector
diffractometer
9728 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
7975 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 1.000Rint = 0.042
39668 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03828 restraints
wR(F2) = 0.093All H-atom parameters refined
S = 1.04Δρmax = 2.08 e Å3
9728 reflectionsΔρmin = 0.54 e Å3
510 parameters
Special details top

Experimental. OXFORD low temperature device.

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. H atoms were restrained to have similar C—H distances.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C00.6874 (4)0.72962 (16)0.72029 (16)0.0128 (6)
C10.6616 (4)0.65897 (17)0.73747 (18)0.0154 (7)
H1A0.662 (5)0.6502 (19)0.7821 (10)0.011 (10)*
H1B0.566 (4)0.644 (2)0.716 (2)0.026 (12)*
O10.7997 (3)0.62098 (12)0.71393 (12)0.0184 (5)
C20.8909 (5)0.58713 (16)0.76047 (17)0.0152 (7)
C31.0636 (5)0.59535 (18)0.76558 (17)0.0183 (7)
C41.1616 (5)0.56147 (19)0.81117 (18)0.0201 (7)
C51.0932 (5)0.51753 (19)0.85359 (17)0.0198 (7)
C60.9202 (5)0.50767 (18)0.84804 (18)0.0207 (7)
C70.8215 (5)0.54139 (18)0.80207 (18)0.0175 (7)
F11.1365 (3)0.63721 (11)0.72512 (11)0.0240 (5)
F21.3281 (3)0.57269 (12)0.81383 (12)0.0256 (5)
F30.8473 (3)0.46500 (12)0.88729 (12)0.0293 (5)
F40.6556 (3)0.53013 (11)0.79721 (12)0.0224 (5)
I11.24282 (4)0.47021 (2)0.92510 (2)0.03126 (8)
C80.8473 (4)0.75684 (17)0.75458 (16)0.0135 (6)
H8A0.940 (4)0.7406 (19)0.7350 (18)0.013 (10)*
H8B0.857 (5)0.8008 (10)0.7508 (19)0.012 (10)*
C90.9445 (4)0.78098 (18)0.86461 (16)0.0157 (7)
C100.8797 (4)0.82522 (18)0.90826 (17)0.0171 (7)
C110.9831 (5)0.86081 (18)0.95143 (17)0.0176 (7)
C121.1559 (5)0.85353 (17)0.95290 (16)0.0170 (7)
C131.2210 (5)0.80928 (18)0.90966 (17)0.0173 (7)
C141.1183 (5)0.77370 (18)0.86650 (17)0.0168 (7)
O20.8390 (3)0.74463 (13)0.82499 (12)0.0192 (5)
F50.7123 (3)0.83272 (12)0.90892 (11)0.0241 (5)
F60.9105 (3)0.90175 (12)0.99275 (12)0.0279 (5)
F71.3870 (3)0.80009 (12)0.90866 (11)0.0249 (5)
F81.1877 (3)0.73036 (12)0.82613 (11)0.0239 (5)
I21.31029 (4)0.90660 (2)1.01837 (2)0.02597 (7)
C150.7072 (5)0.73904 (19)0.64589 (17)0.0161 (7)
H15A0.714 (5)0.7818 (10)0.6374 (19)0.010 (9)*
H15B0.803 (4)0.721 (2)0.633 (2)0.024 (12)*
O30.5646 (3)0.70967 (12)0.60950 (12)0.0186 (5)
C160.4631 (4)0.74785 (18)0.57170 (16)0.0157 (7)
C170.5163 (4)0.79214 (18)0.52491 (17)0.0164 (7)
C180.4019 (5)0.82563 (18)0.48473 (16)0.0166 (7)
C190.2301 (5)0.81733 (18)0.48965 (17)0.0175 (7)
C200.1772 (4)0.77314 (19)0.53568 (18)0.0179 (7)
C210.2898 (5)0.73955 (18)0.57590 (17)0.0182 (7)
F90.6814 (3)0.80003 (12)0.51691 (11)0.0226 (5)
F100.4615 (3)0.86711 (12)0.44021 (11)0.0256 (5)
F110.0129 (3)0.76437 (13)0.54335 (12)0.0295 (5)
F120.2283 (3)0.69714 (12)0.61902 (11)0.0278 (5)
I30.05865 (3)0.87228 (2)0.43353 (2)0.02431 (7)
I40.07305 (3)1.02190 (2)0.86697 (2)0.02284 (7)
C220.5324 (4)0.76548 (17)0.74305 (17)0.0145 (6)
H22A0.436 (3)0.7464 (17)0.7253 (18)0.009 (9)*
H22B0.530 (5)0.7641 (19)0.7882 (10)0.011 (10)*
O40.5447 (3)0.83249 (12)0.72219 (13)0.0195 (5)
C230.4392 (5)0.87347 (17)0.75274 (18)0.0163 (7)
C240.2667 (5)0.87194 (16)0.74154 (18)0.0161 (7)
C250.1639 (4)0.91486 (17)0.77298 (18)0.0161 (7)
C260.2294 (5)0.96073 (16)0.81658 (17)0.0156 (7)
C270.4023 (5)0.96312 (17)0.82737 (18)0.0177 (7)
C280.5057 (5)0.92034 (18)0.79581 (18)0.0181 (7)
F130.1975 (3)0.82806 (10)0.69915 (11)0.0214 (5)
F140.0017 (3)0.91053 (11)0.76005 (12)0.0223 (5)
F150.4729 (3)1.00702 (11)0.86817 (11)0.0243 (5)
F160.6725 (3)0.92467 (12)0.80682 (12)0.0250 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C00.0116 (16)0.0115 (15)0.0148 (14)0.0032 (12)0.0027 (12)0.0006 (12)
C10.0133 (17)0.0122 (16)0.0205 (16)0.0006 (13)0.0013 (13)0.0027 (12)
O10.0207 (13)0.0171 (13)0.0174 (12)0.0100 (10)0.0006 (10)0.0018 (9)
C20.0187 (17)0.0102 (15)0.0167 (15)0.0028 (13)0.0003 (13)0.0027 (12)
C30.0203 (18)0.0180 (18)0.0168 (15)0.0021 (14)0.0032 (13)0.0026 (13)
C40.0168 (18)0.0224 (19)0.0208 (17)0.0005 (15)0.0022 (14)0.0037 (14)
C50.0202 (19)0.0208 (19)0.0176 (16)0.0060 (15)0.0059 (14)0.0017 (13)
C60.028 (2)0.0130 (17)0.0214 (17)0.0007 (15)0.0034 (15)0.0003 (13)
C70.0169 (17)0.0145 (16)0.0210 (16)0.0040 (13)0.0009 (13)0.0038 (13)
F10.0238 (12)0.0220 (12)0.0269 (11)0.0029 (9)0.0090 (9)0.0019 (9)
F20.0147 (11)0.0311 (13)0.0305 (12)0.0014 (9)0.0038 (9)0.0026 (10)
F30.0316 (14)0.0233 (12)0.0329 (13)0.0021 (10)0.0005 (10)0.0100 (10)
F40.0168 (11)0.0186 (11)0.0312 (12)0.0034 (9)0.0031 (9)0.0004 (9)
I10.03263 (16)0.02794 (15)0.03187 (14)0.00387 (11)0.01244 (11)0.00821 (11)
C80.0131 (16)0.0148 (16)0.0125 (14)0.0018 (13)0.0006 (12)0.0000 (12)
C90.0155 (17)0.0180 (17)0.0133 (14)0.0061 (13)0.0038 (12)0.0021 (12)
C100.0129 (17)0.0216 (18)0.0167 (15)0.0009 (14)0.0011 (12)0.0056 (13)
C110.0226 (19)0.0170 (17)0.0131 (14)0.0009 (14)0.0006 (13)0.0003 (12)
C120.0221 (18)0.0147 (16)0.0139 (15)0.0053 (14)0.0041 (13)0.0009 (12)
C130.0143 (17)0.0223 (18)0.0150 (15)0.0040 (14)0.0028 (12)0.0011 (13)
C140.0186 (18)0.0164 (17)0.0154 (15)0.0024 (14)0.0002 (13)0.0005 (12)
O20.0203 (13)0.0232 (14)0.0136 (11)0.0096 (11)0.0045 (9)0.0005 (10)
F50.0120 (10)0.0334 (13)0.0269 (11)0.0013 (9)0.0000 (9)0.0007 (10)
F60.0315 (14)0.0274 (13)0.0248 (11)0.0041 (10)0.0015 (10)0.0110 (10)
F70.0136 (11)0.0354 (14)0.0254 (11)0.0012 (10)0.0026 (9)0.0015 (10)
F80.0204 (12)0.0301 (13)0.0213 (10)0.0025 (10)0.0017 (9)0.0077 (9)
I20.03197 (15)0.02485 (14)0.02000 (12)0.01119 (11)0.01007 (10)0.00024 (9)
C150.0126 (16)0.0210 (18)0.0142 (15)0.0009 (14)0.0030 (12)0.0007 (13)
O30.0176 (13)0.0178 (13)0.0195 (12)0.0019 (10)0.0090 (10)0.0009 (10)
C160.0159 (17)0.0174 (17)0.0135 (14)0.0017 (13)0.0031 (12)0.0017 (12)
C170.0142 (17)0.0191 (17)0.0157 (15)0.0009 (13)0.0006 (12)0.0040 (13)
C180.0190 (18)0.0176 (17)0.0133 (14)0.0002 (14)0.0006 (13)0.0009 (12)
C190.0176 (17)0.0168 (17)0.0179 (15)0.0031 (14)0.0018 (13)0.0022 (13)
C200.0113 (16)0.0228 (19)0.0197 (16)0.0003 (14)0.0007 (13)0.0005 (14)
C210.0210 (18)0.0195 (18)0.0139 (15)0.0001 (14)0.0002 (13)0.0036 (13)
F90.0127 (10)0.0333 (13)0.0217 (10)0.0002 (9)0.0018 (8)0.0030 (9)
F100.0238 (12)0.0287 (13)0.0243 (11)0.0037 (10)0.0005 (9)0.0107 (9)
F110.0133 (11)0.0420 (15)0.0328 (13)0.0044 (10)0.0010 (9)0.0077 (11)
F120.0380 (14)0.0234 (12)0.0228 (11)0.0044 (10)0.0108 (10)0.0116 (9)
I30.02068 (13)0.02714 (14)0.02442 (12)0.00478 (10)0.00593 (9)0.00477 (10)
I40.03133 (15)0.01636 (12)0.02106 (12)0.00833 (10)0.00373 (10)0.00080 (9)
C220.0116 (16)0.0122 (16)0.0196 (16)0.0016 (12)0.0002 (12)0.0007 (12)
O40.0197 (13)0.0116 (12)0.0280 (13)0.0049 (10)0.0093 (11)0.0035 (10)
C230.0158 (17)0.0118 (16)0.0217 (16)0.0030 (13)0.0033 (13)0.0030 (13)
C240.0168 (17)0.0092 (15)0.0222 (16)0.0006 (13)0.0007 (13)0.0015 (12)
C250.0131 (16)0.0116 (16)0.0237 (17)0.0017 (13)0.0008 (13)0.0024 (13)
C260.0195 (18)0.0105 (15)0.0170 (15)0.0018 (13)0.0025 (13)0.0018 (12)
C270.0209 (18)0.0138 (16)0.0181 (16)0.0034 (14)0.0021 (13)0.0018 (13)
C280.0157 (17)0.0134 (16)0.0247 (17)0.0003 (13)0.0035 (14)0.0049 (13)
F130.0207 (11)0.0154 (11)0.0277 (11)0.0003 (9)0.0019 (9)0.0069 (9)
F140.0136 (11)0.0179 (11)0.0352 (12)0.0022 (9)0.0002 (9)0.0023 (9)
F150.0289 (13)0.0201 (11)0.0229 (11)0.0039 (10)0.0082 (9)0.0039 (9)
F160.0112 (11)0.0255 (12)0.0377 (13)0.0007 (9)0.0045 (9)0.0058 (10)
Geometric parameters (Å, º) top
C0—C11.517 (5)C13—C141.379 (5)
C0—C81.528 (5)C14—F81.348 (4)
C0—C151.531 (5)C15—O31.456 (4)
C0—C221.531 (5)C15—H15A0.903 (19)
C1—O11.451 (4)C15—H15B0.91 (2)
C1—H1A0.919 (19)O3—C161.342 (4)
C1—H1B0.91 (2)C16—C171.396 (5)
O1—C21.355 (4)C16—C211.399 (5)
C2—C31.386 (5)C17—F91.344 (4)
C2—C71.396 (5)C17—C181.378 (5)
C3—F11.341 (4)C18—F101.345 (4)
C3—C41.371 (5)C18—C191.389 (5)
C4—F21.346 (4)C19—C201.383 (5)
C4—C51.379 (5)C19—I32.072 (4)
C5—C61.393 (6)C20—F111.339 (4)
C5—I12.073 (4)C20—C211.370 (5)
C6—F31.337 (4)C21—F121.345 (4)
C6—C71.377 (5)I4—C262.076 (3)
C7—F41.341 (4)C22—O41.452 (4)
C8—O21.449 (4)C22—H22A0.920 (19)
C8—H8A0.920 (19)C22—H22B0.913 (19)
C8—H8B0.915 (19)O4—C231.362 (4)
C9—O21.359 (4)C23—C241.383 (5)
C9—C101.387 (5)C23—C281.390 (5)
C9—C141.392 (5)C24—F131.347 (4)
C10—F51.344 (4)C24—C251.383 (5)
C10—C111.382 (5)C25—F141.337 (4)
C11—F61.339 (4)C25—C261.379 (5)
C11—C121.385 (5)C26—C271.385 (5)
C12—C131.382 (5)C27—F151.332 (4)
C12—I22.076 (3)C27—C281.385 (5)
C13—F71.338 (4)C28—F161.340 (4)
C1—C0—C8111.7 (3)F8—C14—C9119.5 (3)
C1—C0—C15111.6 (3)C13—C14—C9121.3 (3)
C8—C0—C15106.0 (3)C9—O2—C8115.2 (3)
C1—C0—C22106.1 (3)O3—C15—C0109.1 (3)
C8—C0—C22110.7 (3)O3—C15—H15A112 (3)
C15—C0—C22110.8 (3)C0—C15—H15A109 (2)
O1—C1—C0109.4 (3)O3—C15—H15B109 (3)
O1—C1—H1A104 (3)C0—C15—H15B111 (3)
C0—C1—H1A115 (3)H15A—C15—H15B107 (4)
O1—C1—H1B107 (3)C16—O3—C15118.5 (3)
C0—C1—H1B109 (3)O3—C16—C17125.2 (3)
H1A—C1—H1B112 (4)O3—C16—C21117.6 (3)
C2—O1—C1116.3 (3)C17—C16—C21117.0 (3)
O1—C2—C3119.1 (3)F9—C17—C18119.5 (3)
O1—C2—C7123.5 (3)F9—C17—C16119.5 (3)
C3—C2—C7117.3 (3)C18—C17—C16120.9 (3)
F1—C3—C4119.2 (3)F10—C18—C17118.0 (3)
F1—C3—C2119.5 (3)F10—C18—C19120.5 (3)
C4—C3—C2121.3 (3)C17—C18—C19121.5 (3)
F2—C4—C3117.9 (3)C20—C19—C18117.6 (3)
F2—C4—C5120.5 (3)C20—C19—I3121.0 (3)
C3—C4—C5121.6 (4)C18—C19—I3121.3 (3)
C4—C5—C6117.8 (3)F11—C20—C21118.7 (3)
C4—C5—I1120.8 (3)F11—C20—C19119.9 (3)
C6—C5—I1121.4 (3)C21—C20—C19121.4 (3)
F3—C6—C7118.9 (4)F12—C21—C20117.7 (3)
F3—C6—C5120.3 (3)F12—C21—C16120.8 (3)
C7—C6—C5120.8 (3)C20—C21—C16121.5 (3)
F4—C7—C6119.4 (3)O4—C22—C0107.9 (3)
F4—C7—C2119.4 (3)O4—C22—H22A111 (2)
C6—C7—C2121.2 (4)C0—C22—H22A110 (2)
O2—C8—C0107.7 (3)O4—C22—H22B109 (3)
O2—C8—H8A116 (3)C0—C22—H22B110 (3)
C0—C8—H8A110 (3)H22A—C22—H22B108 (3)
O2—C8—H8B105 (2)C23—O4—C22114.2 (3)
C0—C8—H8B113 (3)O4—C23—C24122.8 (3)
H8A—C8—H8B105 (4)O4—C23—C28119.5 (3)
O2—C9—C10120.0 (3)C24—C23—C28117.7 (3)
O2—C9—C14122.9 (3)F13—C24—C25119.3 (3)
C10—C9—C14117.0 (3)F13—C24—C23119.6 (3)
F5—C10—C11119.6 (3)C25—C24—C23121.1 (3)
F5—C10—C9118.9 (3)F14—C25—C26120.7 (3)
C11—C10—C9121.5 (3)F14—C25—C24118.0 (3)
F6—C11—C10117.8 (3)C26—C25—C24121.3 (3)
F6—C11—C12121.0 (3)C25—C26—C27117.9 (3)
C10—C11—C12121.2 (3)C25—C26—I4120.9 (3)
C13—C12—C11117.5 (3)C27—C26—I4121.2 (3)
C13—C12—I2121.5 (3)F15—C27—C28118.4 (3)
C11—C12—I2121.0 (3)F15—C27—C26120.6 (3)
F7—C13—C14118.2 (3)C28—C27—C26121.0 (3)
F7—C13—C12120.3 (3)F16—C28—C27119.3 (3)
C14—C13—C12121.5 (3)F16—C28—C23119.7 (3)
F8—C14—C13119.2 (3)C27—C28—C23121.0 (3)
C8—C0—C1—O162.5 (3)C1—C0—C15—O353.9 (4)
C15—C0—C1—O156.0 (4)C8—C0—C15—O3175.7 (3)
C22—C0—C1—O1176.8 (3)C22—C0—C15—O364.1 (4)
C0—C1—O1—C2120.9 (3)C0—C15—O3—C16118.0 (3)
C1—O1—C2—C3126.0 (3)C15—O3—C16—C1750.0 (5)
C1—O1—C2—C757.3 (4)C15—O3—C16—C21134.8 (3)
O1—C2—C3—F11.0 (5)O3—C16—C17—F92.1 (5)
C7—C2—C3—F1177.8 (3)C21—C16—C17—F9177.3 (3)
O1—C2—C3—C4179.0 (3)O3—C16—C17—C18174.9 (3)
C7—C2—C3—C42.1 (5)C21—C16—C17—C180.3 (5)
F1—C3—C4—F21.0 (5)F9—C17—C18—F102.4 (5)
C2—C3—C4—F2179.1 (3)C16—C17—C18—F10179.3 (3)
F1—C3—C4—C5179.5 (3)F9—C17—C18—C19177.7 (3)
C2—C3—C4—C50.4 (6)C16—C17—C18—C190.8 (5)
F2—C4—C5—C6179.5 (3)F10—C18—C19—C20178.9 (3)
C3—C4—C5—C61.0 (6)C17—C18—C19—C201.2 (5)
F2—C4—C5—I12.5 (5)F10—C18—C19—I34.0 (5)
C3—C4—C5—I1177.0 (3)C17—C18—C19—I3175.8 (3)
C4—C5—C6—F3179.1 (3)C18—C19—C20—F11178.6 (3)
I1—C5—C6—F32.9 (5)I3—C19—C20—F111.5 (5)
C4—C5—C6—C70.7 (6)C18—C19—C20—C211.2 (5)
I1—C5—C6—C7177.4 (3)I3—C19—C20—C21175.9 (3)
F3—C6—C7—F40.8 (5)F11—C20—C21—F123.0 (5)
C5—C6—C7—F4179.0 (3)C19—C20—C21—F12179.5 (3)
F3—C6—C7—C2179.1 (3)F11—C20—C21—C16178.2 (3)
C5—C6—C7—C21.1 (6)C19—C20—C21—C160.8 (6)
O1—C2—C7—F40.9 (5)O3—C16—C21—F123.5 (5)
C3—C2—C7—F4177.6 (3)C17—C16—C21—F12179.1 (3)
O1—C2—C7—C6179.2 (3)O3—C16—C21—C20175.3 (3)
C3—C2—C7—C62.4 (5)C17—C16—C21—C200.3 (5)
C1—C0—C8—O254.2 (4)C1—C0—C22—O4175.0 (3)
C15—C0—C8—O2176.0 (3)C8—C0—C22—O463.6 (3)
C22—C0—C8—O263.8 (3)C15—C0—C22—O453.6 (4)
O2—C9—C10—F52.1 (5)C0—C22—O4—C23164.4 (3)
C14—C9—C10—F5178.7 (3)C22—O4—C23—C2468.8 (4)
O2—C9—C10—C11177.0 (3)C22—O4—C23—C28113.0 (4)
C14—C9—C10—C110.4 (5)O4—C23—C24—F130.5 (5)
F5—C10—C11—F60.1 (5)C28—C23—C24—F13178.7 (3)
C9—C10—C11—F6178.9 (3)O4—C23—C24—C25179.3 (3)
F5—C10—C11—C12178.9 (3)C28—C23—C24—C251.1 (5)
C9—C10—C11—C120.2 (5)F13—C24—C25—F140.4 (5)
F6—C11—C12—C13178.6 (3)C23—C24—C25—F14179.8 (3)
C10—C11—C12—C130.1 (5)F13—C24—C25—C26179.8 (3)
F6—C11—C12—I20.8 (5)C23—C24—C25—C260.0 (5)
C10—C11—C12—I2179.5 (3)F14—C25—C26—C27179.4 (3)
C11—C12—C13—F7179.9 (3)C24—C25—C26—C270.8 (5)
I2—C12—C13—F70.6 (5)F14—C25—C26—I42.8 (5)
C11—C12—C13—C140.1 (5)C24—C25—C26—I4177.0 (3)
I2—C12—C13—C14179.5 (3)C25—C26—C27—F15179.0 (3)
F7—C13—C14—F81.3 (5)I4—C26—C27—F153.2 (5)
C12—C13—C14—F8178.9 (3)C25—C26—C27—C280.6 (5)
F7—C13—C14—C9179.7 (3)I4—C26—C27—C28177.2 (3)
C12—C13—C14—C90.1 (6)F15—C27—C28—F160.5 (5)
O2—C9—C14—F82.2 (5)C26—C27—C28—F16179.1 (3)
C10—C9—C14—F8178.6 (3)F15—C27—C28—C23180.0 (3)
O2—C9—C14—C13176.8 (3)C26—C27—C28—C230.5 (5)
C10—C9—C14—C130.4 (5)O4—C23—C28—F160.0 (5)
C10—C9—O2—C8115.1 (4)C24—C23—C28—F16178.3 (3)
C14—C9—O2—C868.6 (4)O4—C23—C28—C27179.5 (3)
C0—C8—O2—C9162.0 (3)C24—C23—C28—C271.3 (5)

Experimental details

Crystal data
Chemical formulaC29H8F16I4O4
Mr1231.95
Crystal system, space groupMonoclinic, P21/n
Temperature (K)90
a, b, c (Å)7.9716 (9), 20.665 (3), 20.194 (4)
β (°) 92.745 (12)
V3)3322.8 (9)
Z4
Radiation typeMo Kα
µ (mm1)3.88
Crystal size (mm)0.34 × 0.06 × 0.04
Data collection
DiffractometerBruker APEX 2000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.742, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
39668, 9728, 7975
Rint0.042
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.093, 1.04
No. of reflections9728
No. of parameters510
No. of restraints28
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)2.08, 0.54

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SIR2002 (Burla et al., 2003), SHELXL2012 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006).

Halogen bonds and C—F···F—C and ππ short interactions (Å, °) top
The distances between the CNTRn of the four TFIP groups showing ππ interactions are also reported (CNTRn is the centroid of the benzene group linking the In iodine atom).
C—X···Y(—C)X···YC—X···YX···Y—C
C5—I1···I3i3.7838 (6)169.59 (11)
C12—I2···F15ii3.323 (3)174.72 (11)
C19—I3···F2iii3.176 (3)162.73 (11)
C26—I4···F6iv3.240 (3)136.47 (11)
C3—F1···(F12—C21)v2.610 (3)162.3 (2)165.1 (3)
C4—F2···(F4—C7)v2.790 (4)150.2 (2)149.5 (3)
C17—F9···(F11—C20)v2.771 (4)151.1 (2)150.6 (3)
C10—F5···(F7—C13)v2.679 (3)158.8 (2)157.2 (3)
C25—F14···(F16—C28)vi2.821 (3)147.6 (2)149.2 (3)
CNTR1···CNTR4i3.643 (6)
C3···C27i3.334 (5)
C16···C11vii3.317 (5)
C18···C9vii3.307 (5)
F9···C13vii3.156 (5)
CNTR2···CNTR3vii3.648 (6)
Symmetry codes: (i) 3/2-x, -1/2+y, 3/2-z; (ii) 2-x, 2-y,2-z; (iii) -3/2+x, 3/2-y, -1/2+z; (iv) 1-x, 2-y, 2-z; (v) x+1,y,z; (vi) x-1,y,z; (vii) -1/2+x, 3/2-y, -1/2+z.
 

Acknowledgements

GC, PM, GR and GT thank the Fondazione Cariplo (projects 2009–2550 and 2010–1351) for financial support.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals
First citationBruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBurla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  CrossRef IUCr Journals
First citationCaronna, T., Liantonio, R., Logothetis, T. A., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Am. Chem. Soc. 126, 4500–4501.  Web of Science CSD CrossRef PubMed CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationGuido, E., Metrangolo, P., Pilati, T. & Resnati, G. (2004). Acta Cryst. E60, o788–o790.  Web of Science CSD CrossRef IUCr Journals
First citationGuido, E., Metrangolo, P., Panzeri, W., Pilati, T., Resnati, G., Ursini, M. & Logothetis, T. A. (2005). J. Fluorine Chem. 126, 197–207.  Web of Science CSD CrossRef CAS
First citationLucassen, A. C. B., Karton, A., Leitus, G., Shimon, L. J. W., Martin, J. M. L. & van der Boom, M. E. (2007). Cryst. Growth Des. 7, 376–392.  Web of Science CSD CrossRef
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationMetrangolo, P., Meyer, F., Pilati, T., Proserpio, D. & Resnati, G. (2007). Chem. Eur. J. 13, 5765–5772.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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Volume 69| Part 4| April 2013| Pages o579-o580
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