Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060564/ng2370sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060564/ng2370Isup2.hkl |
CCDC reference: 674062
Key indicators
- Single-crystal X-ray study
- T = 175 K
- Mean (C-C) = 0.004 Å
- R factor = 0.023
- wR factor = 0.022
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.99 <> 1.01 Calculated formula weight = 717.8020 Formula weight given = 732.6700 CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_weight 732.67 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 14.00 168.15 H 1.01 26.00 26.21 O 16.00 13.00 207.99 F 19.00 6.00 113.99 S 32.07 2.00 64.13 Ba 137.33 1.00 137.33 Calculated formula weight 717.80 DENSD01_ALERT_1_C The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.99 <> 1.01 Crystal density given = 1.835 Calculated crystal density = 1.873 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 732.67 PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT046_ALERT_1_C Reported Z, MW and D(calc) are Inconsistent .... 1.87 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.82 PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S10 - C14 .. 6.23 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S10 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.821 Tmax scaled 0.821 Tmin scaled 0.739
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a similar Ba–18-crown-6 compound, see: Wei et al. (1988). For examples of macrocycle–cation π interactions, see: Arnal-Hérault et al. (2005). For biological and related applications, see: Dougherty (1996); Meyer et al. (2003); Ma & Dougherty (1997). For examples of tubular superstructures, see: Barboiu et al. (2003); Blondeau et al. (2005); Fromm & Bergougnant (2007).
The title compound was prepared by dissolving in acetone (10 ml), in equimolar proportions, 1-(1H-indol-5-yl)-3-phenylurea (0.100 g), 18 C6 (0.105 g) and barium trifluoromethanesulfonate (0.173 g). The metallo-organic compound was crystallized by layering this solution with isopropyl ether. The crystals were formed over two days, by slow diffusion of the non-solvent in the solvent phase. The initial goal of the work was to grow co-crystals of inclusion complexes of Ba-18 C6 bound to the ureido-derivative ligand through cation-π interaction. Indeed, Arnal-Hérault et al. (2005) previously showed that the cation was favourably coordinated by the crown ether while the counter-ion was complexing with the ureido moiety of the co-crystallized ligand.
The H atoms, including those of the water molecule, were all located in a difference map, and repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.87 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996), Mercury (Macrae et al., 2006) and DrawXtl (Finger et al., 2007); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
[Ba2(CF3O3S)2(C12H24O6)2(H2O)2](CF3O3S)2 | Z = 1 |
Mr = 1465.34 | F(000) = 712 |
Triclinic, P1 | Dx = 1.835 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.942 (1) Å | Cell parameters from 23806 reflections |
b = 12.3257 (16) Å | θ = 4–33° |
c = 12.7431 (14) Å | µ = 1.79 mm−1 |
α = 68.629 (12)° | T = 175 K |
β = 87.576 (10)° | Needle, colourless |
γ = 83.212 (10)° | 0.35 × 0.16 × 0.11 mm |
V = 1298.8 (3) Å3 |
Oxford Diffraction GEMINI diffractometer | 9409 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 6364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 33.5°, θmin = 3.8° |
ϕ & ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −18→19 |
Tmin = 0.90, Tmax = 1.00 | l = −19→16 |
23806 measured reflections |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.022 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 19.2 -26.3 13.3 -3.95 |
S = 1.11 | (Δ/σ)max = 0.001 |
6364 reflections | Δρmax = 0.45 e Å−3 |
325 parameters | Δρmin = −0.48 e Å−3 |
0 restraints |
[Ba2(CF3O3S)2(C12H24O6)2(H2O)2](CF3O3S)2 | γ = 83.212 (10)° |
Mr = 1465.34 | V = 1298.8 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.942 (1) Å | Mo Kα radiation |
b = 12.3257 (16) Å | µ = 1.79 mm−1 |
c = 12.7431 (14) Å | T = 175 K |
α = 68.629 (12)° | 0.35 × 0.16 × 0.11 mm |
β = 87.576 (10)° |
Oxford Diffraction GEMINI diffractometer | 9409 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 6364 reflections with I > 2σ(I) |
Tmin = 0.90, Tmax = 1.00 | Rint = 0.022 |
23806 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.022 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.45 e Å−3 |
6364 reflections | Δρmin = −0.48 e Å−3 |
325 parameters |
x | y | z | Uiso*/Ueq | ||
Ba1 | 0.823886 (15) | 0.307417 (11) | 0.715055 (11) | 0.0197 | |
S2 | 0.98425 (6) | 0.57362 (4) | 0.60939 (4) | 0.0214 | |
O3 | 0.82673 (17) | 0.56535 (14) | 0.59766 (13) | 0.0280 | |
O4 | 1.06495 (18) | 0.46352 (14) | 0.67793 (14) | 0.0304 | |
O5 | 1.0606 (2) | 0.63842 (15) | 0.50802 (14) | 0.0329 | |
C6 | 0.9852 (3) | 0.6661 (2) | 0.6942 (2) | 0.0316 | |
F7 | 0.92051 (19) | 0.61984 (15) | 0.79318 (13) | 0.0447 | |
F8 | 0.9110 (2) | 0.77100 (14) | 0.64130 (16) | 0.0568 | |
F9 | 1.1246 (2) | 0.68206 (19) | 0.71126 (17) | 0.0593 | |
S10 | 0.55301 (6) | 0.83623 (5) | 0.86965 (5) | 0.0256 | |
O11 | 0.4194 (2) | 0.8629 (2) | 0.92588 (16) | 0.0484 | |
O12 | 0.6165 (2) | 0.71647 (15) | 0.91215 (17) | 0.0410 | |
O13 | 0.6602 (2) | 0.92020 (17) | 0.84453 (19) | 0.0479 | |
C14 | 0.4807 (3) | 0.8563 (2) | 0.7315 (2) | 0.0361 | |
F15 | 0.4128 (2) | 0.96364 (15) | 0.67946 (14) | 0.0525 | |
F16 | 0.3796 (2) | 0.78288 (17) | 0.73984 (17) | 0.0622 | |
F17 | 0.5887 (2) | 0.8363 (2) | 0.66466 (17) | 0.0740 | |
O18 | 0.55879 (17) | 0.42809 (13) | 0.76730 (13) | 0.0266 | |
C19 | 0.5834 (3) | 0.5078 (2) | 0.8213 (2) | 0.0308 | |
C20 | 0.6720 (3) | 0.4413 (2) | 0.9258 (2) | 0.0348 | |
O21 | 0.81117 (19) | 0.38901 (14) | 0.89606 (13) | 0.0302 | |
C22 | 0.9059 (4) | 0.3309 (3) | 0.9923 (2) | 0.0452 | |
C23 | 1.0526 (3) | 0.2859 (3) | 0.9547 (3) | 0.0488 | |
O24 | 1.0229 (2) | 0.20633 (16) | 0.90171 (15) | 0.0382 | |
C25 | 1.1552 (3) | 0.1405 (3) | 0.8804 (3) | 0.0544 | |
C26 | 1.1083 (4) | 0.0470 (3) | 0.8449 (3) | 0.0536 | |
O27 | 1.0265 (2) | 0.10039 (15) | 0.74158 (15) | 0.0378 | |
C28 | 0.9786 (3) | 0.0131 (2) | 0.7045 (3) | 0.0456 | |
C29 | 0.8885 (3) | 0.0720 (2) | 0.5994 (2) | 0.0430 | |
O30 | 0.7606 (2) | 0.13963 (14) | 0.62381 (14) | 0.0313 | |
C31 | 0.6505 (3) | 0.1803 (2) | 0.5361 (2) | 0.0362 | |
C32 | 0.5118 (3) | 0.2330 (2) | 0.5771 (2) | 0.0359 | |
O33 | 0.54743 (17) | 0.33276 (14) | 0.59967 (13) | 0.0269 | |
C34 | 0.4159 (3) | 0.3861 (3) | 0.6381 (2) | 0.0388 | |
C35 | 0.4590 (3) | 0.4808 (2) | 0.6740 (2) | 0.0340 | |
H36 | 0.3703 | 0.5207 | 0.6964 | 0.0416* | |
H37 | 0.5078 | 0.5375 | 0.6122 | 0.0413* | |
H38 | 0.3740 | 0.3246 | 0.7009 | 0.0500* | |
H39 | 0.3438 | 0.4169 | 0.5780 | 0.0503* | |
H40 | 0.4765 | 0.1765 | 0.6458 | 0.0466* | |
H41 | 0.4322 | 0.2567 | 0.5207 | 0.0471* | |
H42 | 0.6903 | 0.2365 | 0.4685 | 0.0455* | |
H43 | 0.6257 | 0.1139 | 0.5185 | 0.0464* | |
H44 | 0.9487 | 0.1209 | 0.5398 | 0.0525* | |
H45 | 0.8550 | 0.0117 | 0.5767 | 0.0528* | |
H46 | 1.0667 | −0.0352 | 0.6916 | 0.0524* | |
H47 | 0.9167 | −0.0359 | 0.7628 | 0.0518* | |
H48 | 1.1964 | −0.0017 | 0.8344 | 0.0574* | |
H49 | 1.0434 | −0.0014 | 0.9024 | 0.0574* | |
H50 | 1.2142 | 0.1046 | 0.9496 | 0.0613* | |
H51 | 1.2145 | 0.1921 | 0.8223 | 0.0613* | |
H52 | 1.1166 | 0.2439 | 1.0196 | 0.0582* | |
H53 | 1.1021 | 0.3498 | 0.9018 | 0.0580* | |
H54 | 0.9236 | 0.3861 | 1.0276 | 0.0541* | |
H55 | 0.8569 | 0.2662 | 1.0459 | 0.0543* | |
H56 | 0.6949 | 0.4938 | 0.9634 | 0.0436* | |
H57 | 0.6147 | 0.3809 | 0.9773 | 0.0441* | |
H58 | 0.6369 | 0.5710 | 0.7702 | 0.0387* | |
H59 | 0.4879 | 0.5406 | 0.8420 | 0.0391* | |
O60 | 0.6654 (3) | 0.14219 (16) | 0.85835 (16) | 0.0479 | |
H61 | 0.6682 | 0.0712 | 0.8616 | 0.0500* | |
H62 | 0.6264 | 0.1452 | 0.9203 | 0.0500* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ba1 | 0.02160 (5) | 0.01736 (5) | 0.01886 (5) | −0.00117 (3) | 0.00021 (4) | −0.00535 (3) |
S2 | 0.0234 (2) | 0.0229 (2) | 0.0205 (2) | −0.00578 (18) | 0.00364 (17) | −0.01018 (18) |
O3 | 0.0247 (7) | 0.0310 (8) | 0.0309 (8) | −0.0048 (6) | −0.0008 (6) | −0.0137 (6) |
O4 | 0.0271 (8) | 0.0287 (8) | 0.0329 (8) | −0.0013 (6) | 0.0007 (6) | −0.0086 (7) |
O5 | 0.0442 (10) | 0.0322 (8) | 0.0262 (8) | −0.0151 (7) | 0.0139 (7) | −0.0133 (7) |
C6 | 0.0353 (12) | 0.0341 (11) | 0.0342 (12) | −0.0162 (9) | 0.0110 (9) | −0.0203 (10) |
F7 | 0.0561 (10) | 0.0593 (10) | 0.0333 (8) | −0.0285 (8) | 0.0189 (7) | −0.0292 (7) |
F8 | 0.0837 (14) | 0.0319 (8) | 0.0588 (11) | −0.0036 (8) | 0.0180 (10) | −0.0240 (8) |
F9 | 0.0455 (10) | 0.0929 (15) | 0.0712 (12) | −0.0395 (10) | 0.0172 (9) | −0.0593 (12) |
S10 | 0.0262 (2) | 0.0247 (2) | 0.0286 (3) | −0.00262 (19) | −0.0003 (2) | −0.0126 (2) |
O11 | 0.0415 (11) | 0.0666 (14) | 0.0318 (9) | 0.0138 (10) | 0.0028 (8) | −0.0178 (9) |
O12 | 0.0410 (10) | 0.0279 (8) | 0.0532 (12) | 0.0017 (7) | −0.0108 (9) | −0.0143 (8) |
O13 | 0.0494 (12) | 0.0365 (10) | 0.0630 (13) | −0.0178 (9) | −0.0062 (10) | −0.0195 (9) |
C14 | 0.0395 (13) | 0.0369 (12) | 0.0349 (12) | −0.0054 (10) | 0.0018 (10) | −0.0164 (10) |
F15 | 0.0683 (12) | 0.0403 (9) | 0.0386 (9) | 0.0014 (8) | −0.0133 (8) | −0.0030 (7) |
F16 | 0.0720 (13) | 0.0532 (11) | 0.0662 (12) | −0.0212 (10) | −0.0296 (10) | −0.0198 (9) |
F17 | 0.0673 (13) | 0.1174 (19) | 0.0463 (11) | 0.0111 (13) | 0.0071 (9) | −0.0475 (12) |
O18 | 0.0282 (8) | 0.0236 (7) | 0.0288 (8) | 0.0001 (6) | −0.0001 (6) | −0.0115 (6) |
C19 | 0.0336 (12) | 0.0257 (10) | 0.0358 (12) | −0.0024 (9) | 0.0083 (9) | −0.0156 (9) |
C20 | 0.0477 (14) | 0.0323 (11) | 0.0307 (11) | −0.0103 (10) | 0.0082 (10) | −0.0181 (10) |
O21 | 0.0402 (9) | 0.0306 (8) | 0.0201 (7) | −0.0028 (7) | −0.0035 (6) | −0.0094 (6) |
C22 | 0.0611 (18) | 0.0471 (15) | 0.0265 (12) | −0.0050 (13) | −0.0162 (12) | −0.0108 (11) |
C23 | 0.0487 (16) | 0.0527 (17) | 0.0401 (15) | −0.0070 (13) | −0.0205 (13) | −0.0083 (13) |
O24 | 0.0304 (9) | 0.0394 (9) | 0.0376 (9) | 0.0031 (7) | −0.0103 (7) | −0.0063 (8) |
C25 | 0.0251 (12) | 0.079 (2) | 0.0434 (16) | 0.0120 (13) | −0.0069 (11) | −0.0086 (15) |
C26 | 0.0485 (17) | 0.0469 (16) | 0.0449 (16) | 0.0266 (13) | 0.0000 (13) | −0.0022 (13) |
O27 | 0.0385 (9) | 0.0288 (8) | 0.0356 (9) | 0.0087 (7) | 0.0044 (7) | −0.0034 (7) |
C28 | 0.0454 (15) | 0.0235 (11) | 0.0596 (18) | 0.0040 (10) | 0.0164 (13) | −0.0094 (11) |
C29 | 0.0556 (17) | 0.0301 (12) | 0.0480 (15) | −0.0016 (11) | 0.0137 (13) | −0.0222 (11) |
O30 | 0.0411 (9) | 0.0247 (7) | 0.0294 (8) | −0.0011 (7) | 0.0044 (7) | −0.0127 (6) |
C31 | 0.0523 (15) | 0.0336 (12) | 0.0288 (11) | −0.0124 (11) | −0.0006 (10) | −0.0160 (10) |
C32 | 0.0392 (13) | 0.0377 (12) | 0.0345 (12) | −0.0141 (10) | −0.0030 (10) | −0.0142 (10) |
O33 | 0.0242 (7) | 0.0295 (8) | 0.0288 (8) | −0.0040 (6) | −0.0024 (6) | −0.0120 (6) |
C34 | 0.0229 (11) | 0.0525 (16) | 0.0444 (14) | −0.0021 (10) | −0.0009 (10) | −0.0220 (12) |
C35 | 0.0269 (11) | 0.0345 (12) | 0.0387 (13) | 0.0077 (9) | −0.0038 (9) | −0.0140 (10) |
O60 | 0.0825 (15) | 0.0312 (9) | 0.0358 (10) | −0.0251 (10) | 0.0259 (10) | −0.0161 (8) |
Ba1—O3 | 2.9825 (17) | C22—C23 | 1.492 (4) |
Ba1—O4 | 2.9669 (17) | C22—H54 | 0.972 |
Ba1—O5i | 2.8504 (16) | C22—H55 | 0.977 |
Ba1—O18 | 2.8336 (15) | C23—O24 | 1.431 (4) |
Ba1—O21 | 2.8259 (16) | C23—H52 | 0.968 |
Ba1—O24 | 2.8375 (17) | C23—H53 | 0.970 |
Ba1—O27 | 2.8701 (17) | O24—C25 | 1.427 (3) |
Ba1—O30 | 2.8344 (16) | C25—C26 | 1.490 (5) |
Ba1—O33 | 2.8567 (15) | C25—H50 | 0.975 |
Ba1—O60 | 2.6916 (18) | C25—H51 | 0.969 |
O60—Ba1 | 2.6916 (18) | C26—O27 | 1.427 (3) |
O60—O11ii | 2.801 (3) | C26—H48 | 0.967 |
O60—O13iii | 2.811 (3) | C26—H49 | 0.978 |
S2—O3 | 1.4420 (16) | O27—C28 | 1.436 (3) |
S2—O4 | 1.4433 (17) | C28—C29 | 1.488 (4) |
S2—O5 | 1.4406 (16) | C28—H46 | 0.975 |
S2—C6 | 1.835 (2) | C28—H47 | 0.969 |
C6—F7 | 1.321 (3) | C29—O30 | 1.425 (3) |
C6—F8 | 1.329 (3) | C29—H44 | 0.968 |
C6—F9 | 1.323 (3) | C29—H45 | 0.971 |
S10—O11 | 1.4335 (19) | O30—C31 | 1.427 (3) |
S10—O12 | 1.4282 (18) | C31—C32 | 1.494 (4) |
S10—O13 | 1.4348 (19) | C31—H42 | 0.973 |
S10—C14 | 1.822 (3) | C31—H43 | 0.976 |
C14—F15 | 1.328 (3) | C32—O33 | 1.433 (3) |
C14—F16 | 1.328 (3) | C32—H40 | 0.967 |
C14—F17 | 1.322 (3) | C32—H41 | 0.975 |
O18—C19 | 1.430 (3) | O33—C34 | 1.435 (3) |
O18—C35 | 1.422 (3) | C34—C35 | 1.494 (4) |
C19—C20 | 1.488 (4) | C34—H38 | 0.978 |
C19—H58 | 0.975 | C34—H39 | 0.958 |
C19—H59 | 0.969 | C35—H36 | 0.971 |
C20—O21 | 1.434 (3) | C35—H37 | 0.970 |
C20—H56 | 0.977 | O60—H61 | 0.858 |
C20—H57 | 0.977 | O60—H62 | 0.861 |
O21—C22 | 1.428 (3) | ||
O3—Ba1—O4 | 47.65 (4) | O18—C19—H59 | 110.0 |
O3—Ba1—O5i | 68.86 (5) | C20—C19—H59 | 108.5 |
O4—Ba1—O5i | 70.15 (5) | H58—C19—H59 | 109.4 |
O3—Ba1—O18 | 69.95 (5) | C19—C20—O21 | 108.74 (19) |
O4—Ba1—O18 | 106.62 (5) | C19—C20—H56 | 110.5 |
O5i—Ba1—O18 | 123.16 (5) | O21—C20—H56 | 108.5 |
O3—Ba1—O21 | 77.40 (5) | C19—C20—H57 | 109.9 |
O4—Ba1—O21 | 72.76 (5) | O21—C20—H57 | 110.3 |
O5i—Ba1—O21 | 140.95 (5) | H56—C20—H57 | 108.9 |
O18—Ba1—O21 | 57.87 (5) | C20—O21—C22 | 111.26 (19) |
O3—Ba1—O24 | 114.31 (5) | O21—C22—C23 | 108.7 (2) |
O4—Ba1—O24 | 72.98 (5) | O21—C22—H54 | 109.5 |
O5i—Ba1—O24 | 119.71 (6) | C23—C22—H54 | 109.2 |
O18—Ba1—O24 | 112.12 (5) | O21—C22—H55 | 109.4 |
O21—Ba1—O24 | 58.03 (5) | C23—C22—H55 | 110.3 |
O3—Ba1—O27 | 136.71 (5) | H54—C22—H55 | 109.7 |
O4—Ba1—O27 | 94.93 (5) | C22—C23—O24 | 108.0 (2) |
O5i—Ba1—O27 | 79.00 (5) | C22—C23—H52 | 109.5 |
O18—Ba1—O27 | 153.05 (5) | O24—C23—H52 | 108.7 |
O21—Ba1—O27 | 116.26 (5) | C22—C23—H53 | 110.8 |
O3—Ba1—O30 | 128.43 (5) | O24—C23—H53 | 109.7 |
O4—Ba1—O30 | 134.15 (5) | H52—C23—H53 | 110.1 |
O5i—Ba1—O30 | 68.81 (5) | C23—O24—C25 | 113.7 (2) |
O18—Ba1—O30 | 112.40 (5) | O24—C25—C26 | 108.4 (2) |
O21—Ba1—O30 | 150.20 (5) | O24—C25—H50 | 109.0 |
O3—Ba1—O33 | 86.75 (5) | C26—C25—H50 | 109.4 |
O4—Ba1—O33 | 132.11 (5) | O24—C25—H51 | 109.6 |
O5i—Ba1—O33 | 81.31 (5) | C26—C25—H51 | 111.0 |
O18—Ba1—O33 | 58.91 (5) | H50—C25—H51 | 109.5 |
O21—Ba1—O33 | 116.52 (5) | C25—C26—O27 | 109.0 (2) |
O3—Ba1—O60 | 143.63 (5) | C25—C26—H48 | 109.7 |
O4—Ba1—O60 | 149.11 (6) | O27—C26—H48 | 109.7 |
O5i—Ba1—O60 | 136.56 (5) | C25—C26—H49 | 109.8 |
O18—Ba1—O60 | 73.70 (6) | O27—C26—H49 | 109.1 |
O21—Ba1—O60 | 82.49 (5) | H48—C26—H49 | 109.5 |
O24—Ba1—O27 | 58.58 (6) | C26—O27—C28 | 110.8 (2) |
O24—Ba1—O30 | 111.57 (5) | O27—C28—C29 | 109.2 (2) |
O27—Ba1—O30 | 57.95 (5) | O27—C28—H46 | 109.4 |
O24—Ba1—O33 | 153.87 (5) | C29—C28—H46 | 110.7 |
O27—Ba1—O33 | 116.84 (5) | O27—C28—H47 | 108.7 |
O30—Ba1—O33 | 58.94 (5) | C29—C28—H47 | 109.5 |
O24—Ba1—O60 | 78.38 (6) | H46—C28—H47 | 109.3 |
O27—Ba1—O60 | 79.49 (6) | C28—C29—O30 | 108.2 (2) |
O30—Ba1—O60 | 67.77 (5) | C28—C29—H44 | 110.7 |
O3—S2—O4 | 112.80 (10) | O30—C29—H44 | 111.1 |
O3—S2—O5 | 116.11 (10) | C28—C29—H45 | 107.9 |
O4—S2—O5 | 115.10 (10) | O30—C29—H45 | 109.4 |
O3—S2—C6 | 104.15 (10) | H44—C29—H45 | 109.4 |
O4—S2—C6 | 103.97 (11) | C29—O30—C31 | 112.9 (2) |
O5—S2—C6 | 102.62 (10) | O30—C31—C32 | 108.66 (19) |
S2—C6—F7 | 111.90 (15) | O30—C31—H42 | 110.2 |
S2—C6—F8 | 110.42 (18) | C32—C31—H42 | 111.6 |
F7—C6—F8 | 107.6 (2) | O30—C31—H43 | 109.0 |
S2—C6—F9 | 110.85 (16) | C32—C31—H43 | 108.9 |
F7—C6—F9 | 108.3 (2) | H42—C31—H43 | 108.4 |
F8—C6—F9 | 107.6 (2) | C31—C32—O33 | 108.8 (2) |
O11—S10—O12 | 115.32 (13) | C31—C32—H40 | 110.1 |
O11—S10—O13 | 114.89 (14) | O33—C32—H40 | 109.0 |
O12—S10—O13 | 114.95 (12) | C31—C32—H41 | 110.4 |
O11—S10—C14 | 102.02 (12) | O33—C32—H41 | 109.9 |
O12—S10—C14 | 103.74 (12) | H40—C32—H41 | 108.6 |
O13—S10—C14 | 103.41 (13) | C32—O33—C34 | 110.17 (18) |
S10—C14—F15 | 112.46 (18) | O33—C34—C35 | 109.32 (19) |
S10—C14—F16 | 111.11 (18) | O33—C34—H38 | 107.4 |
F15—C14—F16 | 106.6 (2) | C35—C34—H38 | 111.2 |
S10—C14—F17 | 111.77 (19) | O33—C34—H39 | 108.7 |
F15—C14—F17 | 107.8 (2) | C35—C34—H39 | 111.1 |
F16—C14—F17 | 106.8 (2) | H38—C34—H39 | 109.1 |
C19—O18—C35 | 112.02 (17) | C34—C35—O18 | 108.0 (2) |
O18—C19—C20 | 108.15 (18) | C34—C35—H36 | 110.3 |
Ba1—O60—O11ii | 123.03 (8) | O18—C35—H36 | 109.5 |
Ba1—O60—O13iii | 122.84 (8) | C34—C35—H37 | 109.9 |
O11ii—O60—O13iii | 110.59 (9) | O18—C35—H37 | 110.3 |
O18—C19—H58 | 109.6 | H36—C35—H37 | 108.8 |
C20—C19—H58 | 111.1 | H61—O60—H62 | 107.6 |
O(4)—Ba(1)—O(3)—S(2) | 3.37 (7) | O(4)—Ba(1)—O(18)—C(19) | −29.00 (15) |
O(24)—Ba(1)—O(3)—S(2) | 35.53 (9) | Ba(1)—O(27)—C(26)—C(25) | −38.9 (3) |
O(33)—Ba(1)—O(3)—S(2) | −160.50 (8) | C(26)—O(27)—C(28)—C(29) | 177.7 (2) |
O(3)—Ba(1)—O(4)—S(2) | −3.37 (7) | Ba(1)—O(30)—C(31)—C(32) | −52.9 (2) |
O(24)—Ba(1)—O(4)—S(2) | −152.88 (10) | C(34)—O(33)—C(32)—C(31) | 179.39 (19) |
O(33)—Ba(1)—O(4)—S(2) | 18.58 (12) | O(18)—C(19)—C(20)—O(21) | 58.5 (3) |
O(3)—Ba(1)—O(18)—C(19) | −59.98 (14) | O(27)—C(28)—C(29)—O(30) | −60.3 (3) |
O(18)—Ba(1)—O(3)—S(2) | 141.49 (9) | C(28)—O(27)—C(26)—C(25) | −179.8 (2) |
O(27)—Ba(1)—O(3)—S(2) | −33.69 (11) | Ba(1)—O(30)—C(29)—C(28) | 56.3 (2) |
O(60)—Ba(1)—O(3)—S(2) | 139.44 (9) | C(29)—O(30)—C(31)—C(32) | 171.0 (2) |
O(18)—Ba(1)—O(4)—S(2) | −44.24 (9) | Ba(1)—O(33)—C(34)—C(35) | 36.3 (2) |
O(27)—Ba(1)—O(4)—S(2) | 152.13 (8) | O(21)—C(22)—C(23)—O(24) | −59.7 (3) |
O(60)—Ba(1)—O(4)—S(2) | −130.14 (10) | O(30)—C(31)—C(32)—O(33) | 63.1 (2) |
O(3)—Ba(1)—O(18)—C(35) | 70.12 (15) | Ba(1)—O(27)—C(28)—C(29) | 37.2 (3) |
O(21)—Ba(1)—O(3)—S(2) | 81.40 (8) | C(31)—O(30)—C(29)—C(28) | −167.8 (2) |
O(30)—Ba(1)—O(3)—S(2) | −115.32 (8) | Ba(1)—O(33)—C(32)—C(31) | −43.4 (2) |
O(5)i—Ba(1)—O(3)—S(2) | −78.56 (8) | C(32)—O(33)—C(34)—C(35) | 173.37 (19) |
O(21)—Ba(1)—O(4)—S(2) | −91.88 (9) | O(24)—C(25)—C(26)—O(27) | 63.3 (3) |
O(30)—Ba(1)—O(4)—S(2) | 103.31 (9) | O(33)—C(34)—C(35)—O(18) | −63.6 (2) |
O(5)i—Ba(1)—O(4)—S(2) | 75.70 (9) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H47···O13iii | 0.97 | 2.51 | 3.384 (4) | 149 |
C26—H48···O11iv | 0.97 | 2.47 | 3.316 (4) | 146 |
C20—H56···O12 | 0.98 | 2.59 | 3.310 (4) | 130 |
O60—H61···O13iii | 0.86 | 1.96 | 2.811 (4) | 171 |
O60—H62···O11ii | 0.86 | 1.95 | 2.801 (4) | 168 |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z; (iv) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ba2(CF3O3S)2(C12H24O6)2(H2O)2](CF3O3S)2 |
Mr | 1465.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 175 |
a, b, c (Å) | 8.942 (1), 12.3257 (16), 12.7431 (14) |
α, β, γ (°) | 68.629 (12), 87.576 (10), 83.212 (10) |
V (Å3) | 1298.8 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.79 |
Crystal size (mm) | 0.35 × 0.16 × 0.11 |
Data collection | |
Diffractometer | Oxford Diffraction GEMINI diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.90, 1.00 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23806, 9409, 6364 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.777 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.022, 1.11 |
No. of reflections | 6364 |
No. of parameters | 325 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.48 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR2004 (Burla et al., 2003), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), Mercury (Macrae et al., 2006) and DrawXtl (Finger et al., 2007).
Ba1—O3 | 2.9825 (17) | Ba1—O24 | 2.8375 (17) |
Ba1—O4 | 2.9669 (17) | Ba1—O27 | 2.8701 (17) |
Ba1—O5i | 2.8504 (16) | Ba1—O30 | 2.8344 (16) |
Ba1—O18 | 2.8336 (15) | Ba1—O33 | 2.8567 (15) |
Ba1—O21 | 2.8259 (16) | Ba1—O60 | 2.6916 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H47···O13ii | 0.97 | 2.51 | 3.384 (4) | 149 |
C26—H48···O11iii | 0.97 | 2.47 | 3.316 (4) | 146 |
C20—H56···O12 | 0.98 | 2.59 | 3.310 (4) | 130 |
O60—H61···O13ii | 0.86 | 1.96 | 2.811 (4) | 171 |
O60—H62···O11iv | 0.86 | 1.95 | 2.801 (4) | 168 |
Symmetry codes: (ii) x, y−1, z; (iii) x+1, y−1, z; (iv) −x+1, −y+1, −z+2. |
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Macrocycle-cation-π-interactions are of particular biological interest (Dougherty, 1996). In an attempt to co-crystallize an aromatic derivative with a macrocyclic (18-crown-6).(BaTf2) complex (Arnal-Hérault et al., 2005), the latter complex crystallized without the organic compound. Crown-ethers are well known complexants to metal cations, with selective recognition properties relative to the size of the ring. The structure of Ba(C12O8H24).(H2O),(CF3SO3)2 is forming tubular arrays (Barboiu et al., 2003) made of crown ether rings. The oxygen atoms of the crown ether are coordinating the cation in equatorial position while the trifluoromethanesulfonate (CF3SO3 or Tf) anions are coordinating the Ba2+ in apical position. The second apical position is coordinated by a bridging water molecule which is simultaneously H-bonded to both trifluoromethanesulfonate anions (O(Tf)–O(H2O) ≈ 2.805 Å) and coordinated to the Ba2+ cation (Ba–O(H2O) = 2.689 (2) Å). Fig. 1 shows the full coordination pattern of barium ions. Trifluoromethanesulfonate anions are either coordinated to two barium cations, or to two water molecules, them-self coordinated to Ba2+ cations. Each barium cation has the same environment i.e. it is coordinating to ten oxygen atoms of which six from the 18 C6, three from two trifluoromethanesulfonate on one face of the 18 C6 and one from the water molecule on the other face of the 18 C6. The decahedral geometry of barium can be characterized as a sliced distorted tetrahedral environment as depicted in Fig. 2. Molecular columns of barium are formed with an average Ba–Ba distance of 8.5 Å between the anions inside one row (See Fig. 3). Each 18 C6 tube is closely packed to two others through hydrophobic contacts, forming planar sheets. About 7.5 Å separate two rows of barium of one sheet, while the distance between the rows of barium in two distinct sheets is about 9.9 Å. Trifluoromethanesulfonate fluoride atoms close contacts are observed between two sheets (Fig. 4) with F–F = 2.932 (2) Å. The overall packing of the title compound is unusual in the way the trifluoromethanesulfonate anions are inserted between the parallel crown ethers and form supramolecular polymers containing metal cations, counter anions and water molecules. In all crystal structures including trifluoromethanesulfonate and 18 C6, the ion is pushed away in the hydrophobic gaps between the crown ether tubular arrays and does not form an ionic bridge between two metal cations (Wei et al., 1988).