Literature DB >> 23634113

1,3-Bis(2,3,5,6-tetra-fluoro-4-iodo-phen-oxy)-2,2-bis-[(2,3,5,6-tetra-fluoro-4-iodo-phen-oxy)meth-yl]propane.

Gabriella Cavallo1, Pierangelo Metrangolo, Tullio Pilati, Giuseppe Resnati, Giancarlo Terraneo, Maurizio Ursini.   

Abstract

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 inter-molecular inter-actions, consistent with the presence of I and F atoms, and the absence of H atoms, at the periphery of the mol-ecule. In addition, π-π stacking inter-actions between tetra-fluoro-iodo-phenyl (TFIP) groups and five short F⋯F inter-actions are present.

Entities:  

Year:  2013        PMID： 23634113      PMCID： PMC3629626          DOI： 10.1107/S1600536813007605

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 ▶, 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

Crystal data

C29H8F16I4O4 M = 1231.95 Monoclinic, 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 ▶) T min = 0.742, T max = 1.000 39668 measured reflections 9728 independent reflections 7975 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 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 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007605/lh5584sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007605/lh5584Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813007605/lh5584Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C29H8F16I4O4F(000) = 2280
Mr = 1231.95Dx = 2.463 Mg m−3
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 mm−1
β = 92.745 (12)°T = 90 K
V = 3322.8 (9) Å3Neddle, colourless
Z = 40.34 × 0.06 × 0.04 mm
Bruker APEX 2000 CCD area-detector diffractometer9728 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 = −11→11
Tmin = 0.742, Tmax = 1.000k = −29→25
39668 measured reflectionsl = −28→28
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 = 1.04w = 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 Å−3
28 restraintsΔρmin = −0.54 e Å−3
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.
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)
F14−0.0017 (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)
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)
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—O1−62.5 (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—O3−64.1 (4)
C0—C1—O1—C2120.9 (3)C0—C15—O3—C16118.0 (3)
C1—O1—C2—C3−126.0 (3)C15—O3—C16—C1750.0 (5)
C1—O1—C2—C757.3 (4)C15—O3—C16—C21−134.8 (3)
O1—C2—C3—F11.0 (5)O3—C16—C17—F9−2.1 (5)
C7—C2—C3—F1177.8 (3)C21—C16—C17—F9−177.3 (3)
O1—C2—C3—C4−179.0 (3)O3—C16—C17—C18174.9 (3)
C7—C2—C3—C4−2.1 (5)C21—C16—C17—C18−0.3 (5)
F1—C3—C4—F21.0 (5)F9—C17—C18—F10−2.4 (5)
C2—C3—C4—F2−179.1 (3)C16—C17—C18—F10−179.3 (3)
F1—C3—C4—C5−179.5 (3)F9—C17—C18—C19177.7 (3)
C2—C3—C4—C50.4 (6)C16—C17—C18—C190.8 (5)
F2—C4—C5—C6−179.5 (3)F10—C18—C19—C20178.9 (3)
C3—C4—C5—C61.0 (6)C17—C18—C19—C20−1.2 (5)
F2—C4—C5—I12.5 (5)F10—C18—C19—I3−4.0 (5)
C3—C4—C5—I1−177.0 (3)C17—C18—C19—I3175.8 (3)
C4—C5—C6—F3179.1 (3)C18—C19—C20—F11178.6 (3)
I1—C5—C6—F3−2.9 (5)I3—C19—C20—F111.5 (5)
C4—C5—C6—C7−0.7 (6)C18—C19—C20—C211.2 (5)
I1—C5—C6—C7177.4 (3)I3—C19—C20—C21−175.9 (3)
F3—C6—C7—F4−0.8 (5)F11—C20—C21—F123.0 (5)
C5—C6—C7—F4179.0 (3)C19—C20—C21—F12−179.5 (3)
F3—C6—C7—C2179.1 (3)F11—C20—C21—C16−178.2 (3)
C5—C6—C7—C2−1.1 (6)C19—C20—C21—C16−0.8 (6)
O1—C2—C7—F4−0.9 (5)O3—C16—C21—F123.5 (5)
C3—C2—C7—F4−177.6 (3)C17—C16—C21—F12179.1 (3)
O1—C2—C7—C6179.2 (3)O3—C16—C21—C20−175.3 (3)
C3—C2—C7—C62.4 (5)C17—C16—C21—C200.3 (5)
C1—C0—C8—O2−54.2 (4)C1—C0—C22—O4−175.0 (3)
C15—C0—C8—O2−176.0 (3)C8—C0—C22—O463.6 (3)
C22—C0—C8—O263.8 (3)C15—C0—C22—O4−53.6 (4)
O2—C9—C10—F5−2.1 (5)C0—C22—O4—C23−164.4 (3)
C14—C9—C10—F5−178.7 (3)C22—O4—C23—C24−68.8 (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—F6−178.9 (3)O4—C23—C24—C25−179.3 (3)
F5—C10—C11—C12178.9 (3)C28—C23—C24—C25−1.1 (5)
C9—C10—C11—C12−0.2 (5)F13—C24—C25—F140.4 (5)
F6—C11—C12—C13178.6 (3)C23—C24—C25—F14−179.8 (3)
C10—C11—C12—C13−0.1 (5)F13—C24—C25—C26−179.8 (3)
F6—C11—C12—I2−0.8 (5)C23—C24—C25—C260.0 (5)
C10—C11—C12—I2−179.5 (3)F14—C25—C26—C27−179.4 (3)
C11—C12—C13—F7179.9 (3)C24—C25—C26—C270.8 (5)
I2—C12—C13—F7−0.6 (5)F14—C25—C26—I42.8 (5)
C11—C12—C13—C140.1 (5)C24—C25—C26—I4−177.0 (3)
I2—C12—C13—C14179.5 (3)C25—C26—C27—F15179.0 (3)
F7—C13—C14—F81.3 (5)I4—C26—C27—F15−3.2 (5)
C12—C13—C14—F8−178.9 (3)C25—C26—C27—C28−0.6 (5)
F7—C13—C14—C9−179.7 (3)I4—C26—C27—C28177.2 (3)
C12—C13—C14—C90.1 (6)F15—C27—C28—F16−0.5 (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—C13−176.8 (3)C26—C27—C28—C23−0.5 (5)
C10—C9—C14—C13−0.4 (5)O4—C23—C28—F160.0 (5)
C10—C9—O2—C8115.1 (4)C24—C23—C28—F16−178.3 (3)
C14—C9—O2—C8−68.6 (4)O4—C23—C28—C27179.5 (3)
C0—C8—O2—C9−162.0 (3)C24—C23—C28—C271.3 (5)
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)
Table 1

Halogen bonds and C—F⋯F—C and π–π short inter­actions (Å, °)

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

C—X⋯Y(—C) X⋯Y C—X⋯Y X⋯Y—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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  4 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Highly interpenetrated supramolecular networks supported by N...I halogen bonding.

Authors:  Pierangelo Metrangolo; Franck Meyer; Tullio Pilati; Davide M Proserpio; Giuseppe Resnati
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

4.  Halogen bonding and pi...pi stacking control reactivity in the solid state.

Authors:  Tullio Caronna; Rosalba Liantonio; Thomas A Logothetis; Pierangelo Metrangolo; Tullio Pilati; Giuseppe Resnati
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419
  4 in total

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