Literature DB >> 24527019

The 1:1 co-crystal of triphen-yl(2,3,5,6-tetra-fluoro-benz-yl)phospho-nium bromide and 1,1,2,2-tetra-fluoro-1,2-di-iodo-ethane.

Gabriella Cavallo1, Pierangelo Metrangolo1, Franck Meyer2, Tullio Pilati1, Giuseppe Resnati1, Giancarlo Terraneo1.   

Abstract

The title compound, C25H18F4P(+)·Br(-)·C2F4I2, is a 1:1 co-crystal of triphen-yl(2,3,5,6-tetra-fluoro-benz-yl)phospho-nium (TTPB) bromide and 1,1,2,2-tetra-fluoro-1,2-di-iodo-ethane (TFDIE). The crystal structure consists of a framework of TTPB cations held together by C-H⋯Br inter-actions. In this framework, infinite channels along [100] are filled by TFDIE mol-ecules held together in infinite ribbons by short F⋯F [2.863 (2)-2.901 (2)Å] inter-actions. The structure contains halogen bonds (XB) and hydrogen bonds (HB) in the bromide coordination sphere. TFDIE functions as a monodentate XB donor as only one I atom is linked to the Br(-) anion and forms a short and directional inter-action [I⋯Br(-) 3.1798 (7) Å and C-I⋯Br(-) 177.76 (5)°]. The coordination sphere of the bromide anion is completed by two short HBs of about 2.8 Å (for H⋯Br) with the acidic methyl-ene H atoms and two longer HBs of about 3.0 Å with H atoms of the phenyl rings. Surprisingly neither the second iodine atom of TFDIE nor the H atom on the tetra-fluoro-phenyl group make any short contacts.

Entities:  

Year:  2013        PMID： 24527019      PMCID： PMC3914050          DOI： 10.1107/S1600536813032522

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


Related literature

For a general discussion on halogen bonds (XBs) involving anionic halogen-bonding acceptors, see: for oxyanions, Abate et al. (2011 ▶); for chloride and bromide, Abate et al. (2009 ▶); for iodide, Metrangolo et al. (2008 ▶). For examples of reliable XB donors in an ionic context, see: Cavallo et al. (2010 ▶); Metrangolo et al. (2009 ▶); Logothetis et al. (2004 ▶). For different supra­molecular structures of halogen-bonded (poly)anions, see for: discrete adducts, Gattuso et al. (2007 ▶); infinite chains, Gattuso et al. (2006 ▶); comb-like arrays, Biella et al. (2009 ▶); ’ring and stick’ one-dimensional chains, Gattuso et al. (2009 ▶); two-dimensional layers showing Borromean inter­penetration, Liantonio et al. (2006 ▶). For very short XBs in the presence of HBs, see: Cametti et al. (2012 ▶); Gattuso et al. (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For van der Waals radii, see Bondi (1964 ▶).

Experimental

Crystal data

C25H18F4P+·Br−·C2F4I2 M = 859.09 Triclinic, a = 9.6451 (10) Å b = 10.9491 (12) Å c = 13.8425 (15) Å α = 78.07 (2)° β = 79.08 (2)° γ = 76.76 (2)° V = 1376.7 (3) Å3 Z = 2 Mo Kα radiation μ = 3.87 mm−1 T = 90 K 0.26 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.795, T max = 1.000 21807 measured reflections 10912 independent reflections 9550 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.077 S = 1.04 10912 reflections 424 parameters 153 restraints All H-atom parameters refined Δρmax = 1.33 e Å−3 Δρmin = −0.82 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032522/qk2057sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032522/qk2057Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536813032522/qk2057Isup3.cml Additional supporting information: crystallographic information; 3D view; checkCIF report
C25H18F4P+·Br−·C2F4I2Z = 2
Mr = 859.09F(000) = 816
Triclinic, P1Dx = 2.072 Mg m−3
a = 9.6451 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9491 (12) ÅCell parameters from 11010 reflections
c = 13.8425 (15) Åθ = 2.3–34.3°
α = 78.07 (2)°µ = 3.87 mm−1
β = 79.08 (2)°T = 90 K
γ = 76.76 (2)°Prism, colourless
V = 1376.7 (3) Å30.26 × 0.14 × 0.10 mm
Bruker SMART APEX CCD diffractometer9550 reflections with I > 2σ(I)
ω and φ scansRint = 0.021
Absorption correction: multi-scan (SADABS; Bruker, 2005)θmax = 34.8°, θmin = 1.9°
Tmin = 0.795, Tmax = 1.000h = −15→15
21807 measured reflectionsk = −17→17
10912 independent reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077All H-atom parameters refined
S = 1.04w = 1/[σ2(Fo2) + (0.0439P)2 + 0.1396P] where P = (Fo2 + 2Fc2)/3
10912 reflections(Δ/σ)max = 0.002
424 parametersΔρmax = 1.33 e Å−3
153 restraintsΔρmin = −0.82 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 refined by imposing soft restraint (all C—H distances nearly equal, see _iucr_refine_instructions_details)
xyzUiso*/Ueq
P10.22061 (5)0.62628 (4)0.20374 (3)0.01039 (8)
C10.23578 (19)0.57972 (17)0.33387 (13)0.0118 (3)
C20.1283 (2)0.63023 (18)0.40614 (14)0.0158 (3)
H20.054 (2)0.6956 (19)0.3883 (19)0.024 (7)*
C30.1375 (2)0.5875 (2)0.50599 (15)0.0193 (4)
H30.065 (2)0.623 (2)0.5528 (16)0.020 (7)*
C40.2531 (2)0.4930 (2)0.53479 (16)0.0208 (4)
H40.264 (3)0.464 (3)0.5999 (12)0.036 (8)*
C50.3586 (2)0.4403 (2)0.46351 (16)0.0199 (4)
H50.435 (2)0.3789 (19)0.4843 (19)0.021 (7)*
C60.3510 (2)0.48281 (18)0.36277 (15)0.0158 (3)
H60.420 (2)0.446 (2)0.3162 (14)0.010 (5)*
C70.1505 (2)0.50892 (17)0.16526 (14)0.0134 (3)
C80.2253 (2)0.43955 (19)0.09166 (16)0.0194 (4)
H80.3168 (17)0.451 (2)0.0619 (18)0.019 (6)*
C90.1600 (3)0.3527 (2)0.06445 (18)0.0245 (4)
H90.208 (3)0.308 (2)0.0141 (16)0.029 (7)*
C100.0227 (3)0.3377 (2)0.10923 (17)0.0227 (4)
H10−0.029 (3)0.287 (2)0.090 (2)0.029 (7)*
C11−0.0530 (2)0.4085 (2)0.18308 (17)0.0225 (4)
H11−0.1430 (19)0.393 (3)0.215 (2)0.035 (8)*
C120.0113 (2)0.4928 (2)0.21135 (16)0.0188 (4)
H12−0.043 (3)0.542 (2)0.2572 (16)0.025 (7)*
C130.09467 (19)0.77405 (16)0.18385 (13)0.0116 (3)
C140.0966 (2)0.87510 (18)0.23130 (15)0.0157 (3)
H140.156 (2)0.867 (2)0.2793 (15)0.015 (6)*
C150.0025 (2)0.99060 (18)0.20884 (16)0.0170 (4)
H15−0.001 (3)1.0570 (19)0.2419 (18)0.023 (7)*
C16−0.0912 (2)1.00599 (18)0.14058 (16)0.0176 (4)
H16−0.161 (2)1.0804 (18)0.130 (2)0.027 (7)*
C17−0.0919 (2)0.90590 (19)0.09336 (15)0.0167 (4)
H17−0.151 (3)0.917 (3)0.0462 (18)0.038 (8)*
C180.0017 (2)0.79030 (18)0.11510 (14)0.0140 (3)
H180.001 (3)0.726 (2)0.081 (2)0.033 (8)*
C190.39365 (19)0.64217 (17)0.12875 (14)0.0124 (3)
H19A0.452 (2)0.5643 (16)0.1463 (18)0.019 (6)*
H19B0.374 (3)0.657 (2)0.0643 (12)0.021 (7)*
C200.44941 (18)0.75023 (17)0.14995 (13)0.0117 (3)
C210.40228 (19)0.87529 (18)0.10587 (14)0.0138 (3)
F10.31174 (12)0.90025 (11)0.03855 (9)0.0172 (2)
C220.4469 (2)0.97554 (18)0.12931 (15)0.0170 (4)
F20.39219 (14)1.09432 (11)0.08625 (10)0.0231 (3)
C230.5442 (2)0.9558 (2)0.19465 (16)0.0195 (4)
H230.577 (2)1.0179 (18)0.2150 (18)0.015 (6)*
C240.5952 (2)0.8316 (2)0.23629 (15)0.0188 (4)
F30.69239 (14)0.80545 (14)0.29958 (10)0.0262 (3)
C250.5492 (2)0.73121 (18)0.21507 (14)0.0151 (3)
F40.60278 (13)0.61239 (11)0.25752 (10)0.0202 (2)
I10.68637 (2)0.17750 (2)0.35932 (2)0.01447 (3)
C260.7339 (2)0.07462 (18)0.50522 (15)0.0153 (3)
F50.85788 (14)0.09688 (12)0.52343 (10)0.0218 (3)
F60.62843 (14)0.11632 (12)0.57682 (9)0.0215 (3)
C270.7486 (2)−0.06934 (19)0.51369 (15)0.0163 (3)
F70.86111 (13)−0.11245 (12)0.44721 (9)0.0208 (2)
F80.63051 (13)−0.09436 (12)0.49073 (10)0.0203 (2)
I20.78089 (2)−0.17193 (2)0.66122 (2)0.02326 (4)
Br10.61475 (2)0.31789 (2)0.14415 (2)0.01496 (4)
U11U22U33U12U13U23
P10.01231 (18)0.00947 (19)0.00968 (19)−0.00121 (14)−0.00371 (15)−0.00144 (15)
C10.0150 (7)0.0117 (7)0.0099 (7)−0.0031 (6)−0.0044 (6)−0.0022 (6)
C20.0180 (8)0.0153 (8)0.0128 (8)−0.0005 (6)−0.0035 (6)−0.0017 (6)
C30.0225 (9)0.0212 (9)0.0122 (8)−0.0002 (7)−0.0022 (7)−0.0031 (7)
C40.0246 (9)0.0262 (10)0.0105 (8)−0.0030 (8)−0.0049 (7)−0.0007 (7)
C50.0198 (9)0.0208 (9)0.0164 (9)0.0015 (7)−0.0064 (7)0.0002 (7)
C60.0160 (8)0.0152 (8)0.0154 (8)−0.0004 (6)−0.0047 (6)−0.0015 (7)
C70.0172 (8)0.0111 (7)0.0131 (8)−0.0030 (6)−0.0061 (6)−0.0009 (6)
C80.0193 (9)0.0180 (9)0.0234 (10)−0.0006 (7)−0.0064 (7)−0.0095 (8)
C90.0304 (11)0.0173 (9)0.0296 (12)−0.0007 (8)−0.0110 (9)−0.0116 (8)
C100.0351 (11)0.0161 (9)0.0223 (10)−0.0113 (8)−0.0147 (9)0.0006 (7)
C110.0286 (10)0.0239 (10)0.0193 (10)−0.0164 (8)−0.0057 (8)0.0014 (8)
C120.0229 (9)0.0200 (9)0.0160 (9)−0.0098 (7)−0.0017 (7)−0.0033 (7)
C130.0127 (7)0.0096 (7)0.0117 (8)−0.0003 (6)−0.0023 (6)−0.0011 (6)
C140.0161 (8)0.0136 (8)0.0167 (9)−0.0006 (6)−0.0033 (7)−0.0029 (7)
C150.0184 (8)0.0115 (8)0.0192 (9)−0.0016 (6)0.0012 (7)−0.0036 (7)
C160.0140 (8)0.0129 (8)0.0210 (9)0.0013 (6)0.0005 (7)0.0009 (7)
C170.0142 (8)0.0174 (9)0.0165 (9)−0.0002 (6)−0.0054 (7)0.0009 (7)
C180.0142 (7)0.0133 (8)0.0134 (8)−0.0003 (6)−0.0040 (6)−0.0011 (6)
C190.0149 (7)0.0116 (7)0.0104 (7)−0.0011 (6)−0.0039 (6)−0.0015 (6)
C200.0113 (7)0.0138 (8)0.0099 (7)−0.0019 (6)−0.0015 (6)−0.0022 (6)
C210.0121 (7)0.0165 (8)0.0117 (8)−0.0024 (6)−0.0011 (6)−0.0008 (6)
F10.0170 (5)0.0158 (5)0.0172 (6)−0.0012 (4)−0.0066 (4)0.0020 (4)
C220.0186 (8)0.0122 (8)0.0184 (9)−0.0043 (6)0.0027 (7)−0.0024 (7)
F20.0276 (6)0.0126 (5)0.0264 (7)−0.0040 (5)0.0006 (5)−0.0012 (5)
C230.0198 (9)0.0219 (10)0.0192 (9)−0.0099 (7)0.0036 (7)−0.0082 (8)
C240.0171 (8)0.0295 (11)0.0132 (8)−0.0098 (7)−0.0034 (7)−0.0047 (7)
F30.0260 (7)0.0381 (8)0.0212 (7)−0.0136 (6)−0.0116 (5)−0.0045 (6)
C250.0146 (8)0.0176 (8)0.0125 (8)−0.0028 (6)−0.0031 (6)−0.0002 (6)
F40.0214 (6)0.0188 (6)0.0208 (6)−0.0026 (4)−0.0123 (5)0.0029 (5)
I10.01472 (6)0.01475 (6)0.01311 (6)−0.00167 (4)−0.00179 (4)−0.00214 (4)
C260.0162 (8)0.0151 (8)0.0141 (8)−0.0015 (6)−0.0035 (6)−0.0020 (6)
F50.0232 (6)0.0217 (6)0.0248 (7)−0.0083 (5)−0.0109 (5)−0.0026 (5)
F60.0267 (6)0.0208 (6)0.0135 (6)0.0010 (5)0.0009 (5)−0.0046 (5)
C270.0141 (8)0.0183 (9)0.0162 (9)−0.0023 (6)−0.0024 (6)−0.0030 (7)
F70.0197 (6)0.0216 (6)0.0192 (6)0.0011 (5)−0.0004 (5)−0.0071 (5)
F80.0206 (6)0.0190 (6)0.0241 (6)−0.0073 (4)−0.0088 (5)−0.0010 (5)
I20.03227 (8)0.01838 (7)0.01800 (7)−0.00200 (5)−0.00925 (5)0.00110 (5)
Br10.01754 (8)0.01333 (8)0.01289 (8)0.00093 (6)−0.00445 (6)−0.00218 (6)
P1—C71.7917 (19)C14—H140.935 (14)
P1—C131.7920 (18)C15—C161.388 (3)
P1—C11.7922 (19)C15—H150.926 (14)
P1—C191.8153 (19)C16—C171.389 (3)
C1—C21.398 (3)C16—H160.936 (14)
C1—C61.405 (2)C17—C181.389 (3)
C2—C31.377 (3)C17—H170.920 (14)
C2—H20.920 (14)C18—H180.930 (14)
C3—C41.394 (3)C19—C201.507 (3)
C3—H30.932 (14)C19—H19A0.921 (13)
C4—C51.389 (3)C19—H19B0.920 (14)
C4—H40.909 (14)C20—C211.389 (2)
C5—C61.386 (3)C20—C251.394 (3)
C5—H50.924 (14)C21—F11.341 (2)
C6—H60.919 (13)C21—C221.383 (3)
C7—C81.388 (3)C22—F21.345 (2)
C7—C121.406 (3)C22—C231.376 (3)
C8—C91.399 (3)C23—C241.378 (3)
C8—H80.925 (14)C23—H230.922 (13)
C9—C101.382 (3)C24—F31.346 (2)
C9—H90.924 (14)C24—C251.378 (3)
C10—C111.402 (3)C25—F41.340 (2)
C10—H100.934 (14)I1—C262.175 (2)
C11—C121.375 (3)C26—F61.349 (2)
C11—H110.931 (14)C26—F51.351 (2)
C12—H120.921 (14)C26—C271.532 (3)
C13—C181.386 (3)C27—F81.338 (2)
C13—C141.404 (3)C27—F71.347 (2)
C14—C151.393 (3)C27—I22.159 (2)
C7—P1—C13107.23 (9)C16—C15—C14120.78 (19)
C7—P1—C1108.81 (9)C16—C15—H15119.1 (17)
C13—P1—C1109.90 (9)C14—C15—H15120.0 (17)
C7—P1—C19109.70 (9)C15—C16—C17120.20 (17)
C13—P1—C19109.68 (9)C15—C16—H16120.9 (17)
C1—P1—C19111.42 (9)C17—C16—H16118.6 (17)
C2—C1—C6120.18 (17)C16—C17—C18119.52 (18)
C2—C1—P1120.78 (14)C16—C17—H17120.2 (18)
C6—C1—P1118.78 (14)C18—C17—H17120.3 (18)
C3—C2—C1119.93 (17)C13—C18—C17120.53 (18)
C3—C2—H2118.9 (17)C13—C18—H18121.8 (18)
C1—C2—H2121.0 (17)C17—C18—H18117.7 (18)
C2—C3—C4119.94 (18)C20—C19—P1111.81 (12)
C2—C3—H3118.5 (16)C20—C19—H19A112.2 (16)
C4—C3—H3121.6 (16)P1—C19—H19A103.6 (16)
C5—C4—C3120.50 (19)C20—C19—H19B111.5 (16)
C5—C4—H4117 (2)P1—C19—H19B103.4 (17)
C3—C4—H4122 (2)H19A—C19—H19B114 (2)
C6—C5—C4120.15 (18)C21—C20—C25116.27 (17)
C6—C5—H5120.9 (16)C21—C20—C19121.35 (16)
C4—C5—H5119.0 (16)C25—C20—C19122.37 (16)
C5—C6—C1119.28 (18)F1—C21—C22118.80 (17)
C5—C6—H6119.5 (15)F1—C21—C20119.61 (17)
C1—C6—H6121.2 (15)C22—C21—C20121.59 (18)
C8—C7—C12120.72 (18)F2—C22—C23120.42 (18)
C8—C7—P1122.82 (15)F2—C22—C21118.00 (19)
C12—C7—P1116.43 (14)C23—C22—C21121.58 (18)
C7—C8—C9118.7 (2)C22—C23—C24117.24 (19)
C7—C8—H8120.0 (15)C22—C23—H23126.3 (15)
C9—C8—H8121.3 (15)C24—C23—H23116.5 (15)
C10—C9—C8120.5 (2)F3—C24—C25118.05 (19)
C10—C9—H9120.5 (18)F3—C24—C23120.27 (19)
C8—C9—H9119.0 (18)C25—C24—C23121.68 (19)
C9—C10—C11120.7 (2)F4—C25—C24119.11 (17)
C9—C10—H10123.8 (17)F4—C25—C20119.30 (17)
C11—C10—H10115.3 (17)C24—C25—C20121.58 (18)
C12—C11—C10119.2 (2)F6—C26—F5107.16 (16)
C12—C11—H11122.0 (17)F6—C26—C27109.03 (16)
C10—C11—H11118.6 (17)F5—C26—C27108.36 (15)
C11—C12—C7120.16 (19)F6—C26—I1109.67 (12)
C11—C12—H12117.5 (17)F5—C26—I1110.37 (13)
C7—C12—H12122.2 (17)C27—C26—I1112.11 (14)
C18—C13—C14120.25 (16)F8—C27—F7107.53 (16)
C18—C13—P1118.75 (14)F8—C27—C26109.93 (16)
C14—C13—P1120.84 (14)F7—C27—C26108.98 (16)
C15—C14—C13118.72 (18)F8—C27—I2108.64 (13)
C15—C14—H14118.8 (15)F7—C27—I2108.96 (12)
C13—C14—H14122.4 (15)C26—C27—I2112.67 (14)
C7—P1—C1—C2−97.32 (17)C15—C16—C17—C180.1 (3)
C13—P1—C1—C219.81 (18)C14—C13—C18—C17−0.9 (3)
C19—P1—C1—C2141.60 (16)P1—C13—C18—C17−176.34 (15)
C7—P1—C1—C676.88 (17)C16—C17—C18—C130.4 (3)
C13—P1—C1—C6−165.98 (15)C7—P1—C19—C20173.43 (12)
C19—P1—C1—C6−44.20 (18)C13—P1—C19—C2055.90 (15)
C6—C1—C2—C31.9 (3)C1—P1—C19—C20−66.02 (14)
P1—C1—C2—C3175.99 (16)P1—C19—C20—C21−81.71 (19)
C1—C2—C3—C4−0.7 (3)P1—C19—C20—C2597.62 (18)
C2—C3—C4—C5−0.7 (3)C25—C20—C21—F1176.67 (16)
C3—C4—C5—C61.0 (3)C19—C20—C21—F1−4.0 (3)
C4—C5—C6—C10.2 (3)C25—C20—C21—C22−3.0 (3)
C2—C1—C6—C5−1.6 (3)C19—C20—C21—C22176.32 (17)
P1—C1—C6—C5−175.86 (16)F1—C21—C22—F22.8 (3)
C13—P1—C7—C8121.66 (17)C20—C21—C22—F2−177.53 (16)
C1—P1—C7—C8−119.51 (17)F1—C21—C22—C23−177.31 (17)
C19—P1—C7—C82.62 (19)C20—C21—C22—C232.4 (3)
C13—P1—C7—C12−56.18 (17)F2—C22—C23—C24179.70 (17)
C1—P1—C7—C1262.64 (17)C21—C22—C23—C24−0.2 (3)
C19—P1—C7—C12−175.23 (14)C22—C23—C24—F3178.92 (18)
C12—C7—C8—C9−0.3 (3)C22—C23—C24—C25−1.1 (3)
P1—C7—C8—C9−178.07 (16)F3—C24—C25—F4−0.2 (3)
C7—C8—C9—C100.9 (3)C23—C24—C25—F4179.83 (18)
C8—C9—C10—C11−0.5 (3)F3—C24—C25—C20−179.67 (17)
C9—C10—C11—C12−0.5 (3)C23—C24—C25—C200.4 (3)
C10—C11—C12—C71.1 (3)C21—C20—C25—F4−177.76 (16)
C8—C7—C12—C11−0.7 (3)C19—C20—C25—F42.9 (3)
P1—C7—C12—C11177.23 (16)C21—C20—C25—C241.7 (3)
C7—P1—C13—C18−22.55 (18)C19—C20—C25—C24−177.67 (17)
C1—P1—C13—C18−140.67 (15)F6—C26—C27—F867.0 (2)
C19—P1—C13—C1896.51 (16)F5—C26—C27—F8−176.66 (14)
C7—P1—C13—C14162.02 (15)I1—C26—C27—F8−54.61 (18)
C1—P1—C13—C1443.91 (18)F6—C26—C27—F7−175.36 (14)
C19—P1—C13—C14−78.91 (17)F5—C26—C27—F7−59.0 (2)
C18—C13—C14—C150.8 (3)I1—C26—C27—F763.01 (18)
P1—C13—C14—C15176.16 (15)F6—C26—C27—I2−54.30 (18)
C13—C14—C15—C16−0.3 (3)F5—C26—C27—I262.02 (17)
C14—C15—C16—C17−0.2 (3)I1—C26—C27—I2−175.94 (7)
D—H···AD—HH···AD···AD—H···A
C19—H19A···Br10.92 (2)2.80 (2)3.6866 (19)163 (2)
C19—H19B···Br1i0.92 (2)2.83 (2)3.7263 (19)166 (2)
C16—H16···Br1ii0.94 (1)2.99 (2)3.910 (2)168 (2)
C11—H11···Br1iii0.93 (1)3.03 (2)3.725 (2)133 (2)
H···BrC—H···Br
C19—H19A···Br12.797 (15)163 (2)
C19—H19B···Br1i2.826 (15)167 (2)
C16—H16···Br1ii2.991 (15)168 (2)
C11—H11···Br1iii3.025 (15)133 (2)
F···ZC—F···Z
C26—F5···F7i2.863 (2)172.27 (12)
C26—F6···F8ii2.901 (2)102.90 (11)
C27—F7···F5i2.863 (2)117.40 (11)
C27—F8···F8ii2.875 (3)117.65 (12)
C27—F8···F8ii2.875 (3)117.65 (12)
C26—F6···C24iii3.099 (3)170.23 (12)
C27—F7···H2iv2.62 (2)148.9 (6)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C19—H19A⋯Br10.92 (2)2.80 (2)3.6866 (19)163 (2)
C19—H19B⋯Br1i 0.92 (2)2.83 (2)3.7263 (19)166 (2)
C16—H16⋯Br1ii 0.94 (1)2.99 (2)3.910 (2)168 (2)
C11—H11⋯Br1iii 0.93 (1)3.03 (2)3.725 (2)133 (2)

Symmetry codes: (i) ; (ii) ; (iii) .

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Journal:  Acta Crystallogr B       Date:  2002-05-29

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4.  A short history of SHELX.

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

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