Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Halogen bonding (XB) is a highly-directional class of inter­molecular inter­actions that has been used as a powerful tool to drive the design of crystals in the solid phase. To date, the majority of XB donors have been iodine-containing compounds, with many fewer involving brominated analogues. We report the formation of adducts in the vapour phase from a series of di­bromo­perfluoro­alkyl compounds, BrCF2(CF2)nCF2Br (n = 2, 4, 6), and 1,4-di­aza­bicyclo­[2.2.2]octane (DABCO). Single-crystal X-ray diffraction studies of the colourless crystals identified 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,4-di­bromo­perfluoro­butane (1/1), C4Br2F8·C6H12N2, (I), 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,6-di­bromo­perfluoro­hex­ane (1/1), C6Br2F12·C6H12N2, (II), and 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,8-di­bromo­perfluoro­octane (1/1), C8Br2F16·C6H12N2, (III), each of which displays a one-dimensional halogen-bonded network. All three adducts exhibit N...Br distances less than the sum of the van der Waals radii, with butane analogue (I) showing the shortest N...Br halogen-bond distances yet reported between a bromo­perfluoro­carbon and a nitro­gen base [2.809 (3) and 2.818 (3) Å], which are 0.58 and 0.59 Å shorter than the sum of the van der Waals radii.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013663/uk3139sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013663/uk3139Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229617013663/uk3139Isup5.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013663/uk3139IIsup3.hkl
Contains datablock II

mol

MDL mol file https://doi.org/10.1107/S2053229617013663/uk3139IIsup6.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013663/uk3139IIIsup4.hkl
Contains datablock III

mol

MDL mol file https://doi.org/10.1107/S2053229617013663/uk3139IIIsup7.mol
Supplementary material

CCDC references: 1576136; 1576135; 1576134

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II); SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012) for (III). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (I), (II); SHELXL97 (Sheldrick, 2008) for (III). For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,4-Dibromoperfluorobutane–1,4-diazabicyclo[2.2.2]octane (1/1) (I) top
Crystal data top
C4Br2F8·C6H12N2F(000) = 912
Mr = 472.04Dx = 2.027 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.4659 (6) ÅCell parameters from 1842 reflections
b = 11.0854 (6) Åθ = 3.7–27.3°
c = 10.7955 (6) ŵ = 5.32 mm1
β = 106.271 (5)°T = 150 K
V = 1546.96 (15) Å3Block, colourless
Z = 40.2 × 0.2 × 0.15 mm
Data collection top
SuperNova, Single source at offset, Eos
diffractometer
3034 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source2260 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.046
Detector resolution: 8.0714 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = 1416
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1312
Tmin = 0.025, Tmax = 1.000l = 1313
6191 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0076P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3034 reflectionsΔρmax = 0.43 e Å3
199 parametersΔρmin = 0.52 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.47057 (3)0.36072 (4)0.13908 (5)0.02488 (13)
Br20.07338 (3)0.33779 (4)0.18506 (5)0.02532 (13)
C10.3492 (3)0.3537 (4)0.0077 (5)0.0282 (12)
C20.2501 (3)0.3426 (4)0.0330 (4)0.0202 (10)
C30.1478 (3)0.3489 (4)0.0796 (5)0.0208 (10)
C40.0488 (3)0.3080 (4)0.0446 (5)0.0240 (11)
F10.35763 (18)0.2579 (3)0.0792 (3)0.0613 (10)
F20.34425 (18)0.4521 (3)0.0793 (3)0.0598 (10)
F30.25256 (16)0.2386 (2)0.0954 (3)0.0434 (8)
F40.24725 (17)0.4318 (2)0.1146 (3)0.0456 (8)
F50.15754 (17)0.2775 (2)0.1749 (3)0.0408 (8)
F60.13500 (16)0.4625 (2)0.1215 (3)0.0398 (8)
F70.05584 (16)0.1913 (2)0.0158 (3)0.0429 (8)
F80.04251 (17)0.3683 (2)0.0599 (3)0.0387 (7)
C50.6632 (3)0.2423 (4)0.4059 (5)0.0264 (11)
H5A0.69970.19960.35100.032*
H5B0.59740.19960.39920.032*
C60.5907 (3)0.4310 (4)0.4455 (4)0.0297 (12)
H6A0.52390.39170.44150.036*
H6B0.57640.51530.41540.036*
C70.7404 (3)0.4287 (4)0.3691 (4)0.0255 (11)
H7A0.72680.51330.34000.031*
H7B0.77630.38810.31220.031*
C80.7308 (3)0.2414 (4)0.5477 (5)0.0291 (12)
H8A0.69290.20070.60230.035*
H8B0.79500.19530.55410.035*
C90.6604 (3)0.4305 (4)0.5864 (5)0.0317 (12)
H9A0.67630.51450.61660.038*
H9B0.62330.39120.64280.038*
C100.8092 (3)0.4258 (4)0.5097 (5)0.0309 (12)
H10A0.87450.38310.51320.037*
H10B0.82660.50940.54030.037*
N10.6416 (2)0.3667 (3)0.3606 (3)0.0222 (9)
N20.7574 (2)0.3650 (3)0.5949 (4)0.0219 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0157 (2)0.0345 (3)0.0208 (3)0.00078 (18)0.0007 (2)0.0013 (2)
Br20.0159 (2)0.0321 (3)0.0241 (3)0.00058 (18)0.0007 (2)0.0016 (2)
C10.018 (2)0.043 (3)0.020 (3)0.001 (2)0.000 (2)0.000 (3)
C20.022 (2)0.020 (2)0.015 (3)0.0026 (18)0.001 (2)0.004 (2)
C30.021 (2)0.022 (2)0.017 (3)0.0005 (19)0.001 (2)0.002 (2)
C40.020 (2)0.023 (2)0.025 (3)0.0026 (19)0.001 (2)0.002 (2)
F10.0250 (15)0.104 (3)0.049 (2)0.0131 (15)0.0010 (15)0.044 (2)
F20.0290 (15)0.093 (2)0.048 (2)0.0155 (15)0.0049 (15)0.051 (2)
F30.0267 (14)0.0503 (17)0.043 (2)0.0060 (12)0.0069 (14)0.0314 (17)
F40.0265 (14)0.0638 (19)0.040 (2)0.0065 (13)0.0023 (14)0.0322 (18)
F50.0251 (14)0.075 (2)0.0210 (18)0.0005 (13)0.0039 (13)0.0220 (17)
F60.0230 (13)0.0348 (15)0.052 (2)0.0015 (11)0.0045 (14)0.0251 (16)
F70.0246 (14)0.0327 (15)0.066 (3)0.0047 (12)0.0033 (15)0.0202 (16)
F80.0263 (14)0.070 (2)0.0196 (17)0.0058 (13)0.0058 (13)0.0084 (17)
C50.027 (2)0.028 (3)0.022 (3)0.001 (2)0.003 (2)0.003 (2)
C60.026 (2)0.041 (3)0.021 (3)0.008 (2)0.003 (2)0.003 (3)
C70.022 (2)0.031 (3)0.022 (3)0.004 (2)0.004 (2)0.000 (2)
C80.031 (2)0.027 (3)0.025 (3)0.002 (2)0.001 (2)0.003 (2)
C90.026 (2)0.046 (3)0.022 (3)0.010 (2)0.006 (2)0.002 (3)
C100.023 (2)0.036 (3)0.030 (3)0.005 (2)0.003 (2)0.004 (3)
N10.0214 (18)0.030 (2)0.014 (2)0.0003 (16)0.0032 (17)0.0002 (19)
N20.0183 (18)0.027 (2)0.019 (2)0.0008 (15)0.0032 (17)0.0009 (19)
Geometric parameters (Å, º) top
Br1—C11.933 (4)C6—H6A0.9900
Br2—C41.928 (4)C6—H6B0.9900
C1—C21.523 (5)C6—C91.547 (6)
C1—F11.336 (5)C6—N11.472 (5)
C1—F21.328 (5)C7—H7A0.9900
C2—C31.562 (5)C7—H7B0.9900
C2—F31.331 (4)C7—C101.541 (6)
C2—F41.333 (4)C7—N11.477 (4)
C3—C41.551 (5)C8—H8A0.9900
C3—F51.334 (5)C8—H8B0.9900
C3—F61.333 (4)C8—N21.471 (5)
C4—F71.328 (4)C9—H9A0.9900
C4—F81.334 (5)C9—H9B0.9900
C5—H5A0.9900C9—N21.475 (4)
C5—H5B0.9900C10—H10A0.9900
C5—C81.546 (6)C10—H10B0.9900
C5—N11.465 (5)C10—N21.465 (5)
C2—C1—Br1112.0 (3)N1—C6—H6A109.5
F1—C1—Br1108.5 (3)N1—C6—H6B109.5
F1—C1—C2109.0 (3)N1—C6—C9110.5 (3)
F2—C1—Br1109.7 (3)H7A—C7—H7B108.2
F2—C1—C2109.2 (3)C10—C7—H7A109.8
F2—C1—F1108.4 (4)C10—C7—H7B109.8
C1—C2—C3115.2 (4)N1—C7—H7A109.8
F3—C2—C1108.4 (3)N1—C7—H7B109.8
F3—C2—C3108.9 (3)N1—C7—C10109.5 (3)
F3—C2—F4108.0 (4)C5—C8—H8A109.5
F4—C2—C1108.7 (3)C5—C8—H8B109.5
F4—C2—C3107.4 (3)H8A—C8—H8B108.1
C4—C3—C2115.4 (4)N2—C8—C5110.8 (3)
F5—C3—C2108.5 (3)N2—C8—H8A109.5
F5—C3—C4107.0 (3)N2—C8—H8B109.5
F6—C3—C2107.9 (3)C6—C9—H9A109.6
F6—C3—C4108.7 (3)C6—C9—H9B109.6
F6—C3—F5109.3 (4)H9A—C9—H9B108.1
C3—C4—Br2111.2 (3)N2—C9—C6110.2 (4)
F7—C4—Br2109.9 (3)N2—C9—H9A109.6
F7—C4—C3109.4 (3)N2—C9—H9B109.6
F7—C4—F8107.9 (4)C7—C10—H10A109.3
F8—C4—Br2109.7 (3)C7—C10—H10B109.3
F8—C4—C3108.8 (3)H10A—C10—H10B108.0
H5A—C5—H5B108.2N2—C10—C7111.6 (3)
C8—C5—H5A109.6N2—C10—H10A109.3
C8—C5—H5B109.6N2—C10—H10B109.3
N1—C5—H5A109.6C5—N1—C6109.4 (3)
N1—C5—H5B109.6C5—N1—C7109.0 (3)
N1—C5—C8110.1 (3)C6—N1—C7107.7 (3)
H6A—C6—H6B108.1C8—N2—C9108.1 (3)
C9—C6—H6A109.5C10—N2—C8108.8 (3)
C9—C6—H6B109.5C10—N2—C9107.7 (3)
Br1—C1—C2—C3174.3 (3)F5—C3—C4—Br265.9 (4)
Br1—C1—C2—F363.4 (4)F5—C3—C4—F755.6 (5)
Br1—C1—C2—F453.8 (4)F5—C3—C4—F8173.2 (3)
C1—C2—C3—C4166.2 (4)F6—C3—C4—Br251.9 (4)
C1—C2—C3—F546.2 (5)F6—C3—C4—F7173.4 (4)
C1—C2—C3—F672.1 (4)F6—C3—C4—F869.0 (5)
C2—C3—C4—Br2173.3 (3)C5—C8—N2—C960.2 (4)
C2—C3—C4—F765.2 (5)C5—C8—N2—C1056.5 (4)
C2—C3—C4—F852.4 (5)C6—C9—N2—C858.5 (5)
F1—C1—C2—C365.6 (5)C6—C9—N2—C1059.0 (4)
F1—C1—C2—F356.7 (5)C7—C10—N2—C858.4 (4)
F1—C1—C2—F4173.9 (4)C7—C10—N2—C958.6 (4)
F2—C1—C2—C352.6 (5)C8—C5—N1—C657.3 (4)
F2—C1—C2—F3174.9 (4)C8—C5—N1—C760.3 (4)
F2—C1—C2—F467.9 (5)C9—C6—N1—C558.8 (4)
F3—C2—C3—C444.2 (5)C9—C6—N1—C759.5 (4)
F3—C2—C3—F575.8 (4)C10—C7—N1—C558.5 (4)
F3—C2—C3—F6165.9 (3)C10—C7—N1—C660.0 (4)
F4—C2—C3—C472.6 (4)N1—C5—C8—N22.2 (5)
F4—C2—C3—F5167.4 (3)N1—C6—C9—N20.3 (5)
F4—C2—C3—F649.1 (4)N1—C7—C10—N21.0 (5)
1,6-Dibromoperfluorohexane–1,4-diazabicyclo[2.2.2]octane (1/1) (II) top
Crystal data top
C6Br2F12·C6H12N2Z = 2
Mr = 572.06F(000) = 552
Triclinic, P1Dx = 2.121 Mg m3
a = 6.0096 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4941 (8) ÅCell parameters from 4386 reflections
c = 14.5016 (11) Åθ = 3.9–27.1°
α = 92.051 (6)°µ = 4.64 mm1
β = 101.375 (6)°T = 100 K
γ = 90.507 (6)°Block, colourless
V = 895.89 (11) Å30.18 × 0.16 × 0.12 mm
Data collection top
Xcalibur, Atlas
diffractometer
3504 independent reflections
Radiation source: Enhance (Mo) X-ray Source2686 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 5.1636 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1212
Tmin = 0.769, Tmax = 1.000l = 1717
12221 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.021P)2 + 2.803P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3504 reflectionsΔρmax = 0.94 e Å3
253 parametersΔρmin = 0.72 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.69172 (9)0.45860 (5)0.79186 (4)0.01867 (17)
Br20.13706 (9)0.04259 (5)0.20985 (4)0.01959 (17)
F10.7975 (6)0.4096 (5)0.6225 (3)0.0554 (14)
F20.7593 (7)0.2410 (4)0.6992 (3)0.0600 (15)
F30.3387 (6)0.4527 (4)0.6086 (3)0.0399 (10)
F40.3091 (7)0.2778 (4)0.6799 (2)0.0442 (11)
F50.5053 (6)0.3254 (4)0.4718 (2)0.0383 (10)
F60.4927 (6)0.1494 (3)0.5435 (3)0.0388 (10)
F70.0458 (6)0.3529 (3)0.4598 (3)0.0350 (10)
F80.0337 (6)0.1758 (4)0.5308 (2)0.0326 (9)
F90.2375 (7)0.2223 (4)0.3250 (3)0.0463 (12)
F100.2026 (6)0.0481 (4)0.3960 (3)0.0392 (10)
F110.2157 (8)0.2589 (4)0.3024 (3)0.0672 (16)
F120.2544 (6)0.0894 (5)0.3777 (3)0.0560 (14)
C10.6716 (10)0.3545 (6)0.6780 (4)0.0257 (15)
C20.4245 (9)0.3390 (5)0.6239 (4)0.0166 (12)
C30.3941 (10)0.2621 (6)0.5280 (4)0.0197 (13)
C40.1466 (9)0.2400 (6)0.4751 (4)0.0182 (13)
C50.1192 (9)0.1627 (6)0.3800 (4)0.0182 (13)
C60.1253 (10)0.1463 (6)0.3240 (4)0.0263 (15)
N10.7560 (7)0.6409 (4)0.9540 (3)0.0157 (10)
N20.8071 (7)0.8576 (4)1.0479 (3)0.0135 (10)
C70.9959 (8)0.6855 (5)0.9717 (4)0.0154 (12)
H7A1.04480.69260.91220.019*
H7B1.09100.62381.00840.019*
C81.0238 (9)0.8163 (6)1.0254 (4)0.0185 (13)
H8A1.13580.81031.08310.022*
H8B1.07790.87910.98710.022*
C90.6153 (9)0.7392 (5)0.9010 (4)0.0175 (13)
H9A0.45740.71160.88770.021*
H9B0.66230.75070.84150.021*
C100.6408 (9)0.8669 (5)0.9587 (4)0.0184 (13)
H10A0.68970.93320.92180.022*
H10B0.49470.89060.97240.022*
C110.6861 (9)0.6296 (5)1.0452 (4)0.0166 (12)
H11A0.77240.56331.08030.020*
H11B0.52650.60571.03460.020*
C120.7259 (9)0.7576 (5)1.1030 (4)0.0190 (13)
H12A0.58520.78411.12060.023*
H12B0.83720.74621.16020.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0226 (3)0.0185 (4)0.0139 (3)0.0010 (2)0.0020 (2)0.0039 (2)
Br20.0238 (3)0.0191 (4)0.0138 (3)0.0006 (2)0.0006 (2)0.0040 (2)
F10.029 (2)0.109 (4)0.030 (2)0.026 (2)0.0163 (19)0.030 (2)
F20.063 (3)0.039 (3)0.057 (3)0.034 (2)0.037 (2)0.027 (2)
F30.048 (2)0.027 (2)0.035 (2)0.0166 (18)0.0128 (19)0.0137 (18)
F40.047 (2)0.068 (3)0.018 (2)0.033 (2)0.0093 (18)0.006 (2)
F50.033 (2)0.067 (3)0.0161 (19)0.0233 (19)0.0109 (16)0.0084 (19)
F60.042 (2)0.023 (2)0.041 (2)0.0170 (17)0.0157 (18)0.0147 (18)
F70.038 (2)0.027 (2)0.032 (2)0.0178 (16)0.0109 (17)0.0101 (17)
F80.030 (2)0.053 (3)0.0147 (18)0.0173 (17)0.0070 (16)0.0038 (17)
F90.054 (3)0.067 (3)0.021 (2)0.036 (2)0.0193 (19)0.011 (2)
F100.048 (2)0.025 (2)0.034 (2)0.0192 (17)0.0139 (18)0.0131 (18)
F110.078 (3)0.043 (3)0.056 (3)0.043 (2)0.043 (3)0.032 (2)
F120.030 (2)0.107 (4)0.032 (2)0.023 (2)0.0144 (19)0.033 (2)
C10.030 (3)0.025 (4)0.021 (3)0.004 (3)0.003 (3)0.007 (3)
C20.020 (3)0.015 (3)0.015 (3)0.001 (2)0.004 (2)0.002 (2)
C30.024 (3)0.015 (3)0.022 (3)0.001 (2)0.010 (3)0.002 (3)
C40.019 (3)0.019 (3)0.017 (3)0.001 (2)0.003 (2)0.003 (3)
C50.017 (3)0.022 (4)0.016 (3)0.000 (2)0.004 (2)0.001 (3)
C60.024 (3)0.028 (4)0.025 (4)0.007 (3)0.001 (3)0.006 (3)
N10.016 (2)0.017 (3)0.013 (2)0.0002 (19)0.001 (2)0.004 (2)
N20.016 (2)0.008 (3)0.016 (2)0.0036 (18)0.0005 (19)0.0035 (19)
C70.012 (3)0.019 (3)0.014 (3)0.003 (2)0.001 (2)0.002 (2)
C80.017 (3)0.023 (4)0.014 (3)0.001 (2)0.001 (2)0.001 (2)
C90.020 (3)0.013 (3)0.016 (3)0.001 (2)0.003 (2)0.006 (2)
C100.022 (3)0.016 (3)0.016 (3)0.005 (2)0.001 (2)0.001 (2)
C110.019 (3)0.012 (3)0.019 (3)0.006 (2)0.006 (2)0.002 (2)
C120.017 (3)0.020 (3)0.020 (3)0.000 (2)0.004 (2)0.001 (3)
Geometric parameters (Å, º) top
Br1—C11.930 (6)N1—C91.479 (7)
Br2—C61.937 (6)N1—C111.472 (7)
F1—C11.349 (7)N2—C81.468 (7)
F2—C11.328 (7)N2—C101.476 (7)
F3—C21.313 (6)N2—C121.477 (7)
F4—C21.343 (6)C7—H7A0.9700
F5—C31.341 (7)C7—H7B0.9700
F6—C31.334 (7)C7—C81.545 (7)
F7—C41.341 (7)C8—H8A0.9700
F8—C41.346 (6)C8—H8B0.9700
F9—C51.337 (6)C9—H9A0.9700
F10—C51.318 (7)C9—H9B0.9700
F11—C61.327 (7)C9—C101.545 (7)
F12—C61.351 (8)C10—H10A0.9700
C1—C21.541 (8)C10—H10B0.9700
C2—C31.560 (8)C11—H11A0.9700
C3—C41.545 (8)C11—H11B0.9700
C4—C51.553 (8)C11—C121.549 (7)
C5—C61.537 (8)C12—H12A0.9700
N1—C71.482 (6)C12—H12B0.9700
F1—C1—Br1108.9 (4)C8—N2—C10108.2 (4)
F1—C1—C2109.2 (5)C8—N2—C12107.9 (4)
F2—C1—Br1109.5 (4)C10—N2—C12108.0 (4)
F2—C1—F1107.4 (5)N1—C7—H7A109.5
F2—C1—C2110.1 (5)N1—C7—H7B109.5
C2—C1—Br1111.6 (4)N1—C7—C8110.8 (4)
F3—C2—F4109.0 (5)H7A—C7—H7B108.1
F3—C2—C1108.7 (5)C8—C7—H7A109.5
F3—C2—C3108.7 (5)C8—C7—H7B109.5
F4—C2—C1107.0 (5)N2—C8—C7110.8 (4)
F4—C2—C3108.3 (4)N2—C8—H8A109.5
C1—C2—C3115.0 (5)N2—C8—H8B109.5
F5—C3—C2107.9 (4)C7—C8—H8A109.5
F5—C3—C4108.0 (5)C7—C8—H8B109.5
F6—C3—F5107.7 (5)H8A—C8—H8B108.1
F6—C3—C2108.4 (5)N1—C9—H9A109.6
F6—C3—C4108.9 (4)N1—C9—H9B109.6
C4—C3—C2115.7 (5)N1—C9—C10110.1 (4)
F7—C4—F8107.2 (5)H9A—C9—H9B108.1
F7—C4—C3109.3 (4)C10—C9—H9A109.6
F7—C4—C5109.0 (5)C10—C9—H9B109.6
F8—C4—C3108.4 (4)N2—C10—C9111.3 (4)
F8—C4—C5107.5 (4)N2—C10—H10A109.4
C3—C4—C5115.1 (5)N2—C10—H10B109.4
F9—C5—C4108.4 (5)C9—C10—H10A109.4
F9—C5—C6106.9 (5)C9—C10—H10B109.4
F10—C5—F9108.8 (5)H10A—C10—H10B108.0
F10—C5—C4109.1 (5)N1—C11—H11A109.5
F10—C5—C6107.8 (5)N1—C11—H11B109.5
C6—C5—C4115.6 (5)N1—C11—C12110.6 (4)
F11—C6—Br2109.5 (4)H11A—C11—H11B108.1
F11—C6—F12107.1 (5)C12—C11—H11A109.5
F11—C6—C5110.6 (5)C12—C11—H11B109.5
F12—C6—Br2108.7 (4)N2—C12—C11110.8 (4)
F12—C6—C5109.4 (5)N2—C12—H12A109.5
C5—C6—Br2111.5 (4)N2—C12—H12B109.5
C9—N1—C7108.0 (4)C11—C12—H12A109.5
C11—N1—C7108.5 (4)C11—C12—H12B109.5
C11—N1—C9108.1 (4)H12A—C12—H12B108.1
Br1—C1—C2—F354.7 (6)F10—C5—C6—Br255.4 (6)
Br1—C1—C2—F462.8 (5)F10—C5—C6—F11177.4 (5)
Br1—C1—C2—C3176.8 (4)F10—C5—C6—F1264.9 (6)
F1—C1—C2—F365.8 (6)C1—C2—C3—F561.8 (6)
F1—C1—C2—F4176.7 (5)C1—C2—C3—F654.6 (6)
F1—C1—C2—C356.3 (7)C1—C2—C3—C4177.2 (5)
F2—C1—C2—F3176.6 (5)C2—C3—C4—F757.3 (6)
F2—C1—C2—F459.1 (6)C2—C3—C4—F859.3 (6)
F2—C1—C2—C361.3 (7)C2—C3—C4—C5179.7 (5)
F3—C2—C3—F560.3 (6)C3—C4—C5—F956.7 (6)
F3—C2—C3—F6176.6 (4)C3—C4—C5—F1061.6 (6)
F3—C2—C3—C460.8 (6)C3—C4—C5—C6176.8 (5)
F4—C2—C3—F5178.6 (5)C4—C5—C6—Br2177.7 (4)
F4—C2—C3—F665.1 (6)C4—C5—C6—F1160.3 (7)
F4—C2—C3—C457.5 (6)C4—C5—C6—F1257.4 (7)
F5—C3—C4—F763.7 (6)N1—C7—C8—N22.6 (6)
F5—C3—C4—F8179.7 (5)N1—C9—C10—N23.2 (6)
F5—C3—C4—C559.3 (6)N1—C11—C12—N24.1 (6)
F6—C3—C4—F7179.6 (5)C7—N1—C9—C1060.1 (5)
F6—C3—C4—F863.0 (6)C7—N1—C11—C1255.6 (6)
F6—C3—C4—C557.4 (6)C8—N2—C10—C956.6 (6)
F7—C4—C5—F966.4 (6)C8—N2—C12—C1161.1 (5)
F7—C4—C5—F10175.2 (4)C9—N1—C7—C857.2 (5)
F7—C4—C5—C653.6 (7)C9—N1—C11—C1261.3 (5)
F8—C4—C5—F9177.6 (5)C10—N2—C8—C759.6 (6)
F8—C4—C5—F1059.3 (6)C10—N2—C12—C1155.7 (6)
F8—C4—C5—C662.3 (7)C11—N1—C7—C859.7 (6)
F9—C5—C6—Br261.5 (6)C11—N1—C9—C1057.1 (5)
F9—C5—C6—F1160.6 (7)C12—N2—C8—C757.0 (6)
F9—C5—C6—F12178.3 (5)C12—N2—C10—C960.0 (6)
1,8-Dibromoperfluorooctane–1,4-diazabicyclo[2.2.2]octane (1/1) (III) top
Crystal data top
C8Br2F16·C6H12N2Z = 2
Mr = 672.08F(000) = 648
Triclinic, P1Dx = 2.157 Mg m3
a = 6.03367 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4836 (5) ÅCell parameters from 4902 reflections
c = 16.4471 (9) Åθ = 3.7–28.5°
α = 88.785 (4)°µ = 4.07 mm1
β = 84.126 (3)°T = 150 K
γ = 89.724 (3)°Plate, colourless
V = 1034.65 (8) Å30.14 × 0.08 × 0.04 mm
Data collection top
SuperNova Single source at offset Eos
diffractometer
4680 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3723 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.042
Detector resolution: 8.0714 pixels mm-1θmax = 27.5°, θmin = 3.4°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1313
Tmin = 0.622, Tmax = 1.000l = 2021
14918 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0543P)2 + 1.8052P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4680 reflectionsΔρmax = 1.01 e Å3
307 parametersΔρmin = 0.69 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.23740 (7)0.52567 (4)0.18081 (3)0.02372 (14)
Br20.31570 (7)0.97270 (4)0.81774 (3)0.02532 (14)
F11.3167 (7)0.7383 (4)0.2593 (3)0.0833 (16)
F21.3831 (5)0.5669 (5)0.3265 (2)0.0725 (13)
F30.8768 (5)0.6934 (4)0.28024 (19)0.0543 (10)
F40.9322 (5)0.5136 (3)0.34060 (19)0.0451 (8)
F51.0979 (5)0.8127 (3)0.3973 (2)0.0527 (10)
F61.1252 (5)0.6296 (3)0.45864 (18)0.0488 (9)
F70.6478 (5)0.7905 (3)0.40831 (18)0.0478 (9)
F80.6682 (5)0.6037 (3)0.4658 (2)0.0432 (8)
F90.8583 (5)0.8949 (3)0.5291 (2)0.0516 (10)
F100.8853 (5)0.7085 (3)0.58647 (18)0.0528 (10)
F110.4022 (5)0.8649 (4)0.53924 (19)0.0505 (9)
F120.4369 (5)0.6839 (3)0.6011 (2)0.0546 (10)
F130.5997 (6)0.9860 (3)0.6536 (2)0.0494 (9)
F140.6676 (6)0.8086 (4)0.71488 (19)0.0603 (11)
F150.1540 (5)0.9307 (5)0.6751 (2)0.0803 (15)
F160.2275 (8)0.7598 (4)0.7402 (3)0.098 (2)
C71.2412 (8)0.6223 (5)0.2782 (3)0.0330 (11)
C81.0085 (6)0.6313 (4)0.3270 (3)0.0208 (9)
C91.0034 (7)0.6992 (4)0.4097 (3)0.0228 (9)
C100.7661 (7)0.7177 (4)0.4556 (3)0.0206 (9)
C110.7649 (7)0.7810 (4)0.5399 (3)0.0225 (9)
C120.5298 (7)0.7974 (4)0.5869 (3)0.0242 (9)
C130.5292 (7)0.8682 (4)0.6694 (3)0.0219 (9)
C140.3021 (8)0.8752 (5)0.7208 (3)0.0378 (13)
N10.7315 (5)0.6447 (3)0.0400 (2)0.0189 (7)
N20.7042 (5)0.8534 (3)0.0414 (2)0.0189 (7)
C10.8227 (7)0.6268 (4)0.0389 (3)0.0238 (9)
H1A0.97900.60370.02960.029*
H1B0.74480.55750.06960.029*
C20.4988 (6)0.6868 (4)0.0243 (3)0.0217 (9)
H2A0.41330.62160.00750.026*
H2B0.43560.69830.07590.026*
C30.8580 (7)0.7475 (4)0.0859 (3)0.0238 (9)
H3A0.79610.76400.13720.029*
H3B1.01190.72110.09810.029*
C40.8483 (7)0.8712 (4)0.0353 (3)0.0243 (9)
H4A0.99720.89350.02330.029*
H4B0.79140.94090.06700.029*
C50.4823 (6)0.8127 (4)0.0220 (3)0.0217 (9)
H5A0.41880.87830.01110.026*
H5B0.38450.80160.07230.026*
C60.7980 (7)0.7497 (4)0.0891 (3)0.0242 (9)
H6A0.70120.73360.13900.029*
H6B0.94270.77500.10400.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0275 (2)0.0276 (3)0.0159 (2)0.00098 (16)0.00033 (16)0.00486 (18)
Br20.0299 (2)0.0282 (3)0.0170 (3)0.00127 (17)0.00269 (17)0.00512 (18)
F10.106 (3)0.060 (2)0.071 (3)0.059 (2)0.064 (2)0.044 (2)
F20.0323 (17)0.149 (4)0.040 (2)0.029 (2)0.0150 (15)0.043 (2)
F30.059 (2)0.087 (3)0.0182 (17)0.0405 (18)0.0105 (14)0.0067 (16)
F40.064 (2)0.0318 (16)0.0356 (19)0.0178 (14)0.0164 (15)0.0122 (14)
F50.0584 (19)0.0421 (18)0.052 (2)0.0298 (15)0.0295 (16)0.0262 (16)
F60.0370 (16)0.093 (3)0.0180 (16)0.0294 (16)0.0096 (12)0.0065 (16)
F70.0454 (17)0.080 (2)0.0193 (16)0.0333 (16)0.0079 (13)0.0037 (15)
F80.0454 (17)0.0393 (17)0.0413 (19)0.0196 (13)0.0169 (14)0.0185 (14)
F90.0539 (18)0.0433 (18)0.052 (2)0.0283 (14)0.0289 (16)0.0260 (16)
F100.0505 (18)0.092 (3)0.0169 (16)0.0429 (18)0.0122 (13)0.0055 (16)
F110.0364 (16)0.093 (3)0.0236 (17)0.0310 (16)0.0106 (13)0.0121 (17)
F120.063 (2)0.0417 (18)0.052 (2)0.0320 (15)0.0318 (17)0.0249 (16)
F130.072 (2)0.0342 (17)0.0369 (19)0.0213 (15)0.0241 (16)0.0136 (14)
F140.062 (2)0.101 (3)0.0196 (17)0.049 (2)0.0153 (15)0.0143 (18)
F150.0312 (17)0.165 (4)0.049 (2)0.033 (2)0.0147 (16)0.055 (3)
F160.133 (4)0.071 (3)0.075 (3)0.073 (3)0.077 (3)0.050 (2)
C70.032 (2)0.046 (3)0.021 (3)0.009 (2)0.0049 (19)0.012 (2)
C80.021 (2)0.023 (2)0.018 (2)0.0001 (16)0.0047 (16)0.0028 (18)
C90.021 (2)0.029 (2)0.018 (2)0.0047 (17)0.0010 (16)0.0028 (18)
C100.023 (2)0.026 (2)0.013 (2)0.0003 (16)0.0043 (16)0.0019 (17)
C110.022 (2)0.027 (2)0.019 (2)0.0018 (16)0.0033 (17)0.0048 (19)
C120.025 (2)0.028 (2)0.019 (2)0.0044 (17)0.0010 (17)0.0046 (19)
C130.023 (2)0.024 (2)0.019 (2)0.0018 (16)0.0033 (16)0.0005 (18)
C140.035 (3)0.047 (3)0.029 (3)0.012 (2)0.012 (2)0.017 (2)
N10.0191 (16)0.0215 (18)0.0164 (19)0.0004 (13)0.0025 (13)0.0072 (15)
N20.0208 (17)0.0172 (17)0.018 (2)0.0011 (13)0.0004 (13)0.0043 (14)
C10.030 (2)0.021 (2)0.022 (2)0.0070 (17)0.0097 (18)0.0025 (18)
C20.0173 (19)0.025 (2)0.023 (2)0.0029 (15)0.0036 (16)0.0046 (18)
C30.026 (2)0.025 (2)0.019 (2)0.0050 (17)0.0036 (17)0.0069 (18)
C40.025 (2)0.022 (2)0.024 (3)0.0053 (16)0.0036 (17)0.0060 (18)
C50.0177 (19)0.027 (2)0.021 (2)0.0033 (16)0.0028 (16)0.0040 (18)
C60.031 (2)0.023 (2)0.020 (2)0.0058 (17)0.0081 (18)0.0033 (18)
Geometric parameters (Å, º) top
Br1—C71.915 (5)C12—C131.560 (6)
Br2—C141.921 (5)C13—C141.537 (6)
F1—C71.321 (6)N1—C11.469 (5)
F2—C71.347 (6)N1—C21.469 (5)
F3—C81.321 (5)N1—C31.472 (5)
F4—C81.326 (5)N2—C41.466 (5)
F5—C91.325 (5)N2—C51.474 (5)
F6—C91.346 (5)N2—C61.471 (5)
F7—C101.334 (5)C1—H1A0.9700
F8—C101.336 (5)C1—H1B0.9700
F9—C111.323 (5)C1—C61.543 (6)
F10—C111.333 (5)C2—H2A0.9700
F11—C121.343 (5)C2—H2B0.9700
F12—C121.323 (5)C2—C51.536 (5)
F13—C131.320 (5)C3—H3A0.9700
F14—C131.323 (5)C3—H3B0.9700
F15—C141.348 (7)C3—C41.554 (6)
F16—C141.314 (6)C4—H4A0.9700
C7—C81.547 (6)C4—H4B0.9700
C8—C91.547 (6)C5—H5A0.9700
C9—C101.562 (6)C5—H5B0.9700
C10—C111.549 (6)C6—H6A0.9700
C11—C121.555 (6)C6—H6B0.9700
F1—C7—Br1109.7 (3)F16—C14—F15106.7 (5)
F1—C7—F2107.2 (5)F16—C14—C13110.3 (4)
F1—C7—C8109.4 (4)C13—C14—Br2112.0 (3)
F2—C7—Br1109.2 (3)C1—N1—C3108.0 (3)
F2—C7—C8108.7 (4)C2—N1—C1108.3 (3)
C8—C7—Br1112.5 (3)C2—N1—C3108.0 (3)
F3—C8—F4108.8 (4)C4—N2—C5108.6 (3)
F3—C8—C7107.4 (4)C4—N2—C6108.2 (3)
F3—C8—C9108.9 (3)C6—N2—C5107.8 (3)
F4—C8—C7107.8 (3)N1—C1—H1A109.5
F4—C8—C9108.7 (4)N1—C1—H1B109.5
C9—C8—C7115.1 (3)N1—C1—C6110.9 (3)
F5—C9—F6108.2 (4)H1A—C1—H1B108.0
F5—C9—C8108.9 (4)C6—C1—H1A109.5
F5—C9—C10108.4 (3)C6—C1—H1B109.5
F6—C9—C8108.1 (3)N1—C2—H2A109.4
F6—C9—C10108.0 (4)N1—C2—H2B109.4
C8—C9—C10115.0 (3)N1—C2—C5111.1 (3)
F7—C10—F8108.4 (4)H2A—C2—H2B108.0
F7—C10—C9108.0 (4)C5—C2—H2A109.4
F7—C10—C11108.6 (3)C5—C2—H2B109.4
F8—C10—C9108.4 (3)N1—C3—H3A109.6
F8—C10—C11109.1 (4)N1—C3—H3B109.6
C11—C10—C9114.2 (3)N1—C3—C4110.4 (3)
F9—C11—F10109.2 (4)H3A—C3—H3B108.1
F9—C11—C10108.7 (4)C4—C3—H3A109.6
F9—C11—C12108.4 (3)C4—C3—H3B109.6
F10—C11—C10108.2 (3)N2—C4—C3110.6 (3)
F10—C11—C12107.6 (4)N2—C4—H4A109.5
C10—C11—C12114.7 (4)N2—C4—H4B109.5
F11—C12—C11108.5 (4)C3—C4—H4A109.5
F11—C12—C13107.7 (3)C3—C4—H4B109.5
F12—C12—F11107.7 (4)H4A—C4—H4B108.1
F12—C12—C11109.4 (3)N2—C5—C2110.6 (3)
F12—C12—C13109.1 (4)N2—C5—H5A109.5
C11—C12—C13114.2 (4)N2—C5—H5B109.5
F13—C13—F14109.1 (4)C2—C5—H5A109.5
F13—C13—C12108.6 (4)C2—C5—H5B109.5
F13—C13—C14108.0 (4)H5A—C5—H5B108.1
F14—C13—C12108.7 (4)N2—C6—C1110.5 (4)
F14—C13—C14107.0 (4)N2—C6—H6A109.5
C14—C13—C12115.4 (4)N2—C6—H6B109.5
F15—C14—Br2108.7 (3)C1—C6—H6A109.5
F15—C14—C13108.7 (4)C1—C6—H6B109.5
F16—C14—Br2110.2 (4)H6A—C6—H6B108.1
Br1—C7—C8—F363.1 (4)F13—C13—C14—Br255.0 (5)
Br1—C7—C8—F454.0 (5)F13—C13—C14—F1565.2 (5)
Br1—C7—C8—C9175.5 (3)F13—C13—C14—F16178.2 (5)
F1—C7—C8—F359.2 (5)F14—C13—C14—Br262.4 (5)
F1—C7—C8—F4176.2 (4)F14—C13—C14—F15177.5 (4)
F1—C7—C8—C962.3 (6)F14—C13—C14—F1660.8 (6)
F2—C7—C8—F3175.9 (4)C7—C8—C9—F553.5 (5)
F2—C7—C8—F467.0 (5)C7—C8—C9—F663.8 (5)
F2—C7—C8—C954.5 (5)C7—C8—C9—C10175.4 (4)
F3—C8—C9—F567.1 (5)C8—C9—C10—F761.4 (5)
F3—C8—C9—F6175.6 (4)C8—C9—C10—F855.9 (5)
F3—C8—C9—C1054.8 (5)C8—C9—C10—C11177.7 (4)
F4—C8—C9—F5174.5 (3)C9—C10—C11—F959.7 (5)
F4—C8—C9—F657.1 (4)C9—C10—C11—F1058.8 (5)
F4—C8—C9—C1063.6 (5)C9—C10—C11—C12178.8 (3)
F5—C9—C10—F760.8 (5)C10—C11—C12—F1156.5 (5)
F5—C9—C10—F8178.0 (4)C10—C11—C12—F1260.7 (5)
F5—C9—C10—C1160.1 (5)C10—C11—C12—C13176.7 (4)
F6—C9—C10—F7177.8 (4)C11—C12—C13—F1364.0 (5)
F6—C9—C10—F864.9 (4)C11—C12—C13—F1454.6 (5)
F6—C9—C10—C1156.9 (5)C11—C12—C13—C14174.8 (4)
F7—C10—C11—F960.9 (5)C12—C13—C14—Br2176.6 (3)
F7—C10—C11—F10179.4 (3)C12—C13—C14—F1556.4 (5)
F7—C10—C11—C1260.6 (5)C12—C13—C14—F1660.2 (6)
F8—C10—C11—F9178.8 (3)N1—C1—C6—N23.9 (5)
F8—C10—C11—F1062.7 (4)N1—C2—C5—N22.6 (5)
F8—C10—C11—C1257.3 (5)N1—C3—C4—N23.7 (5)
F9—C11—C12—F1165.1 (5)C1—N1—C2—C559.6 (4)
F9—C11—C12—F12177.6 (4)C1—N1—C3—C456.4 (4)
F9—C11—C12—C1355.0 (5)C2—N1—C1—C655.8 (4)
F10—C11—C12—F11176.9 (4)C2—N1—C3—C460.5 (4)
F10—C11—C12—F1259.6 (5)C3—N1—C1—C660.9 (4)
F10—C11—C12—C1362.9 (5)C3—N1—C2—C557.1 (4)
F11—C12—C13—F1356.6 (4)C4—N2—C5—C259.9 (4)
F11—C12—C13—F14175.2 (4)C4—N2—C6—C156.5 (4)
F11—C12—C13—C1464.6 (5)C5—N2—C4—C356.1 (4)
F12—C12—C13—F13173.3 (4)C5—N2—C6—C160.8 (4)
F12—C12—C13—F1468.1 (5)C6—N2—C4—C360.7 (4)
F12—C12—C13—C1452.0 (5)C6—N2—C5—C257.2 (4)
N···Br halogen bond distances (Å) in the current work and previously reported structures top
EntryDonorAcceptorN···BrRefcodeReference
1Br(CF2)8BrMe2N-C6H4-NMe22.922 (3)VAQROVLiantonio et al. (2003)
2Br(CF2)2BrMe2NCH2CH2NMe22.862 (5)REMBOBHuang et al. (2006)
3Br(CF2)2BrDABCO2.829 (3)KURMANBrisdon et al. (2015)
4Br(CF2)4BrDABCO2.814 (3)av-This work
5Br(CF2)6BrDABCO2.949 (4)av-This work
6Br(CF2)8BrDABCO2.958 (3)av-This work
Intermolecular F···H and F···F contact distances (Å) less than the sum of the van der Waals radii and their difference. top
AdductXYX···YDifference
KURMANF1H2A2.66-0.01
(I)F3H7Ai2.60-0.08
F7H10Bi2.62-0.05
(II)F9H9Bii2.63-0.04
F3F5ii2.872 (6)-0.068
F6F10iii2.825 (5)-0.115
(III)F14H3Aiv2.66-0.01
F5F13v2.852 (5)-0.090
F9F9v2.882 (4)-0.058
F4F10vi2.864 (4)-0.080
Symmetry codes: (i) -x+1, y-1/2, -z+1/2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y, z+1; (v) -x+2, -y+2, -z+1; (vi) -x+2, -y+1, -z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds