Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101016109/bk1618sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101016109/bk1618Isup2.hkl |
CCDC reference: 175116
For related literature, see: Bryan et al. (1998); Dale (1980); Hay & Hancock (2001); Hay et al. (1996); Pedersen (1967); Sachleben et al. (1996, 1997); Talanova et al. (1999); Tobe et al. (1998); Vögtle & Weber (1992).
Tribenzo-18-crown-6 was prepared as described elsewhere (Pedersen, 1967). Crystals were prepared by slow evaporation of an acetonitrile solution.
The crystals slowly desolvate when removed from the mother liquor. Crystals were removed from the mother liquor to paraffin oil, then quickly mounted and placed under the diffractometer's cold stream. A 1.1 mm collimator was used. All H atoms were placed in calculated positions, treated as riding on their attached C atoms, and given an isotropic displacement parameter equal to 1.2 (CH, CH2) or 1.5 (CH3) times the equivalent isotropic displacement parameter of the atom to which they were attached. The C—H distances used depended on the type of C atom: methylene C—H = 0.99 Å and arene C—H = 0.95 Å. The positional parameters of the methyl H atoms were allowed to refine [C—H = 0.92 (2)–1.00 (2) Å.
Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C24H24O6·2C2H3N | Z = 2 |
Mr = 490.5 | F(000) = 520 |
Triclinic, P1 | Dx = 1.29 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.109 (2) Å | Cell parameters from 25 reflections |
b = 10.883 (3) Å | θ = 10.1–15.1° |
c = 13.964 (4) Å | µ = 0.09 mm−1 |
α = 110.16 (2)° | T = 100 K |
β = 96.60 (2)° | Block, colourless |
γ = 98.27 (2)° | 0.56 × 0.49 × 0.43 mm |
V = 1265.7 (6) Å3 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.016 |
Radiation source: fine-focus sealed tube | θmax = 29.0°, θmin = 2.0° |
Graphite monochromator | h = −12→6 |
ω scans | k = −14→14 |
7849 measured reflections | l = −18→19 |
6714 independent reflections | 3 standard reflections every 120 min |
5308 reflections with I > 2σ(I) | intensity decay: 12% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2556P] where P = (Fo2 + 2Fc2)/3 |
6714 reflections | (Δ/σ)max = 0.001 |
343 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
0 constraints |
C24H24O6·2C2H3N | γ = 98.27 (2)° |
Mr = 490.5 | V = 1265.7 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.109 (2) Å | Mo Kα radiation |
b = 10.883 (3) Å | µ = 0.09 mm−1 |
c = 13.964 (4) Å | T = 100 K |
α = 110.16 (2)° | 0.56 × 0.49 × 0.43 mm |
β = 96.60 (2)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.016 |
7849 measured reflections | 3 standard reflections every 120 min |
6714 independent reflections | intensity decay: 12% |
5308 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.34 e Å−3 |
6714 reflections | Δρmin = −0.27 e Å−3 |
343 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.05609 (9) | −0.11117 (8) | 0.38135 (6) | 0.0186 (2) | |
O2 | −0.12291 (9) | −0.08200 (8) | 0.23342 (6) | 0.0192 (2) | |
O3 | 0.02536 (9) | 0.07881 (8) | 0.13621 (7) | 0.0203 (2) | |
O4 | 0.31311 (9) | 0.11543 (8) | 0.14322 (6) | 0.0210 (2) | |
O5 | 0.48959 (9) | 0.16230 (8) | 0.34147 (6) | 0.0206 (2) | |
O6 | 0.35578 (9) | 0.05222 (8) | 0.45557 (6) | 0.0183 (2) | |
C1 | −0.04773 (12) | −0.22320 (11) | 0.31835 (8) | 0.0181 (3) | |
C2 | −0.14416 (12) | −0.20684 (11) | 0.23912 (8) | 0.0178 (3) | |
C3 | −0.25265 (13) | −0.31475 (12) | 0.17173 (9) | 0.0220 (3) | |
C4 | −0.26616 (15) | −0.43861 (13) | 0.18205 (10) | 0.0262 (3) | |
C5 | −0.17243 (15) | −0.45447 (13) | 0.25964 (10) | 0.0265 (3) | |
C6 | −0.06243 (14) | −0.34697 (12) | 0.32804 (9) | 0.0224 (3) | |
C7 | −0.18316 (13) | −0.08118 (12) | 0.13434 (9) | 0.0202 (3) | |
C8 | −0.13442 (13) | 0.05471 (12) | 0.13071 (9) | 0.0203 (3) | |
C9 | 0.08811 (13) | 0.19306 (11) | 0.12325 (8) | 0.0192 (3) | |
C10 | 0.24568 (13) | 0.21391 (11) | 0.12786 (8) | 0.0190 (3) | |
C11 | 0.31871 (14) | 0.32500 (12) | 0.11254 (9) | 0.0230 (3) | |
C12 | 0.23673 (16) | 0.41543 (12) | 0.09300 (9) | 0.0256 (3) | |
C13 | 0.08313 (16) | 0.39590 (13) | 0.08990 (10) | 0.0267 (4) | |
C14 | 0.00829 (15) | 0.28463 (13) | 0.10523 (9) | 0.0238 (3) | |
C15 | 0.47462 (13) | 0.13953 (13) | 0.16578 (9) | 0.0216 (3) | |
C16 | 0.53751 (13) | 0.23140 (12) | 0.27620 (9) | 0.0214 (3) | |
C17 | 0.52053 (13) | 0.23507 (11) | 0.44631 (9) | 0.0190 (3) | |
C18 | 0.44695 (12) | 0.17534 (11) | 0.50758 (9) | 0.0185 (3) | |
C19 | 0.46831 (14) | 0.24354 (13) | 0.61395 (9) | 0.0237 (3) | |
C20 | 0.56407 (15) | 0.36840 (13) | 0.65968 (10) | 0.0286 (3) | |
C21 | 0.63902 (15) | 0.42513 (13) | 0.60021 (10) | 0.0282 (3) | |
C22 | 0.61674 (14) | 0.35873 (12) | 0.49279 (10) | 0.0237 (3) | |
C23 | 0.26779 (13) | 0.00082 (12) | 0.51737 (8) | 0.0195 (3) | |
C24 | 0.17051 (13) | −0.13154 (12) | 0.45067 (9) | 0.0195 (3) | |
N1 | −0.06974 (14) | 0.34722 (14) | 0.37634 (10) | 0.0376 (4) | |
C25 | 0.13874 (16) | 0.21267 (16) | 0.38968 (11) | 0.0299 (4) | |
C26 | 0.02294 (14) | 0.28886 (13) | 0.38161 (9) | 0.0244 (3) | |
N2 | 0.39136 (15) | −0.23808 (13) | 0.04374 (10) | 0.0372 (4) | |
C27 | 0.23452 (18) | −0.15528 (16) | 0.18940 (12) | 0.0314 (4) | |
C28 | 0.32199 (14) | −0.20203 (13) | 0.10756 (10) | 0.0256 (3) | |
H3 | −0.31800 | −0.30400 | 0.11830 | 0.0260* | |
H4 | −0.34010 | −0.51210 | 0.13550 | 0.0310* | |
H5 | −0.18240 | −0.53880 | 0.26680 | 0.0320* | |
H6 | 0.00240 | −0.35870 | 0.38120 | 0.0270* | |
H7A | −0.29460 | −0.10460 | 0.12220 | 0.0240* | |
H7B | −0.14700 | −0.14860 | 0.07910 | 0.0240* | |
H8A | −0.18510 | 0.05870 | 0.06550 | 0.0240* | |
H8B | −0.16210 | 0.12350 | 0.18970 | 0.0240* | |
H11 | 0.42470 | 0.33950 | 0.11540 | 0.0280* | |
H12 | 0.28700 | 0.49070 | 0.08180 | 0.0310* | |
H13 | 0.02800 | 0.45820 | 0.07730 | 0.0320* | |
H14 | −0.09760 | 0.27160 | 0.10330 | 0.0290* | |
H15A | 0.51600 | 0.17940 | 0.11820 | 0.0260* | |
H15B | 0.50760 | 0.05330 | 0.15300 | 0.0260* | |
H16A | 0.64890 | 0.25320 | 0.28710 | 0.0260* | |
H16B | 0.49900 | 0.31550 | 0.29220 | 0.0260* | |
H19 | 0.41760 | 0.20510 | 0.65570 | 0.0280* | |
H20 | 0.57770 | 0.41470 | 0.73250 | 0.0340* | |
H21 | 0.70570 | 0.50920 | 0.63220 | 0.0340* | |
H22 | 0.66740 | 0.39820 | 0.45160 | 0.0280* | |
H23A | 0.20380 | 0.06430 | 0.54940 | 0.0230* | |
H23B | 0.33550 | −0.00970 | 0.57360 | 0.0230* | |
H24A | 0.23260 | −0.19100 | 0.41060 | 0.0230* | |
H24B | 0.12330 | −0.17450 | 0.49460 | 0.0230* | |
H25A | 0.202 (2) | 0.2162 (18) | 0.3421 (15) | 0.0450* | |
H25B | 0.088 (2) | 0.118 (2) | 0.3723 (14) | 0.0450* | |
H25C | 0.196 (2) | 0.2535 (18) | 0.4591 (15) | 0.0450* | |
H27A | 0.168 (2) | −0.1038 (19) | 0.1701 (15) | 0.0470* | |
H27B | 0.181 (2) | −0.228 (2) | 0.1985 (15) | 0.0470* | |
H27C | 0.302 (2) | −0.095 (2) | 0.2510 (16) | 0.0470* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0170 (4) | 0.0206 (4) | 0.0168 (4) | 0.0025 (3) | −0.0012 (3) | 0.0071 (3) |
O2 | 0.0214 (4) | 0.0205 (4) | 0.0138 (4) | 0.0009 (3) | −0.0011 (3) | 0.0066 (3) |
O3 | 0.0162 (4) | 0.0235 (4) | 0.0231 (4) | 0.0021 (3) | 0.0018 (3) | 0.0120 (3) |
O4 | 0.0167 (4) | 0.0239 (4) | 0.0218 (4) | 0.0016 (3) | −0.0002 (3) | 0.0098 (3) |
O5 | 0.0220 (4) | 0.0218 (4) | 0.0153 (4) | 0.0004 (3) | 0.0005 (3) | 0.0060 (3) |
O6 | 0.0172 (4) | 0.0210 (4) | 0.0139 (4) | 0.0014 (3) | 0.0016 (3) | 0.0042 (3) |
C1 | 0.0170 (5) | 0.0214 (5) | 0.0155 (5) | 0.0034 (4) | 0.0050 (4) | 0.0058 (4) |
C2 | 0.0174 (5) | 0.0203 (5) | 0.0153 (5) | 0.0018 (4) | 0.0048 (4) | 0.0063 (4) |
C3 | 0.0198 (5) | 0.0251 (6) | 0.0180 (5) | −0.0001 (4) | 0.0023 (4) | 0.0063 (4) |
C4 | 0.0249 (6) | 0.0223 (6) | 0.0257 (6) | −0.0042 (5) | 0.0049 (5) | 0.0051 (5) |
C5 | 0.0284 (6) | 0.0209 (6) | 0.0309 (6) | 0.0024 (5) | 0.0092 (5) | 0.0102 (5) |
C6 | 0.0224 (6) | 0.0235 (6) | 0.0234 (6) | 0.0054 (4) | 0.0062 (4) | 0.0102 (5) |
C7 | 0.0175 (5) | 0.0260 (6) | 0.0153 (5) | 0.0003 (4) | −0.0017 (4) | 0.0083 (4) |
C8 | 0.0153 (5) | 0.0271 (6) | 0.0187 (5) | 0.0033 (4) | −0.0003 (4) | 0.0101 (4) |
C9 | 0.0222 (5) | 0.0213 (5) | 0.0127 (5) | 0.0022 (4) | 0.0011 (4) | 0.0061 (4) |
C10 | 0.0223 (5) | 0.0208 (5) | 0.0110 (5) | 0.0014 (4) | −0.0006 (4) | 0.0044 (4) |
C11 | 0.0242 (6) | 0.0236 (6) | 0.0162 (5) | −0.0027 (5) | −0.0009 (4) | 0.0054 (4) |
C12 | 0.0364 (7) | 0.0200 (6) | 0.0168 (5) | −0.0013 (5) | 0.0009 (5) | 0.0063 (4) |
C13 | 0.0369 (7) | 0.0239 (6) | 0.0207 (6) | 0.0082 (5) | 0.0028 (5) | 0.0099 (5) |
C14 | 0.0257 (6) | 0.0269 (6) | 0.0203 (5) | 0.0067 (5) | 0.0029 (5) | 0.0103 (5) |
C15 | 0.0165 (5) | 0.0281 (6) | 0.0199 (5) | 0.0028 (4) | 0.0036 (4) | 0.0088 (5) |
C16 | 0.0175 (5) | 0.0248 (6) | 0.0211 (5) | 0.0006 (4) | 0.0017 (4) | 0.0093 (5) |
C17 | 0.0168 (5) | 0.0211 (5) | 0.0165 (5) | 0.0053 (4) | −0.0005 (4) | 0.0043 (4) |
C18 | 0.0144 (5) | 0.0211 (5) | 0.0165 (5) | 0.0046 (4) | −0.0006 (4) | 0.0033 (4) |
C19 | 0.0200 (5) | 0.0296 (6) | 0.0169 (5) | 0.0056 (5) | 0.0018 (4) | 0.0030 (5) |
C20 | 0.0264 (6) | 0.0285 (6) | 0.0196 (6) | 0.0046 (5) | −0.0004 (5) | −0.0032 (5) |
C21 | 0.0249 (6) | 0.0213 (6) | 0.0281 (6) | 0.0020 (5) | −0.0027 (5) | −0.0004 (5) |
C22 | 0.0209 (5) | 0.0216 (6) | 0.0255 (6) | 0.0029 (4) | −0.0002 (4) | 0.0066 (5) |
C23 | 0.0178 (5) | 0.0275 (6) | 0.0142 (5) | 0.0056 (4) | 0.0029 (4) | 0.0084 (4) |
C24 | 0.0179 (5) | 0.0252 (6) | 0.0177 (5) | 0.0049 (4) | 0.0016 (4) | 0.0111 (4) |
N1 | 0.0308 (6) | 0.0509 (8) | 0.0398 (7) | 0.0158 (6) | 0.0061 (5) | 0.0242 (6) |
C25 | 0.0253 (6) | 0.0378 (8) | 0.0277 (7) | 0.0113 (6) | 0.0025 (5) | 0.0122 (6) |
C26 | 0.0217 (6) | 0.0325 (6) | 0.0205 (6) | 0.0034 (5) | 0.0015 (4) | 0.0131 (5) |
N2 | 0.0345 (6) | 0.0383 (7) | 0.0339 (6) | 0.0026 (5) | 0.0136 (5) | 0.0068 (5) |
C27 | 0.0334 (7) | 0.0337 (7) | 0.0310 (7) | 0.0088 (6) | 0.0150 (6) | 0.0128 (6) |
C28 | 0.0237 (6) | 0.0270 (6) | 0.0249 (6) | 0.0023 (5) | 0.0042 (5) | 0.0092 (5) |
O1—C1 | 1.3757 (15) | C23—C24 | 1.4987 (18) |
O1—C24 | 1.4335 (15) | C3—H3 | 0.95 |
O2—C2 | 1.3755 (16) | C4—H4 | 0.95 |
O2—C7 | 1.4321 (15) | C5—H5 | 0.95 |
O3—C8 | 1.4296 (15) | C6—H6 | 0.95 |
O3—C9 | 1.3711 (16) | C7—H7B | 0.99 |
O4—C10 | 1.3746 (16) | C7—H7A | 0.99 |
O4—C15 | 1.4346 (15) | C8—H8B | 0.99 |
O5—C16 | 1.4340 (16) | C8—H8A | 0.99 |
O5—C17 | 1.3754 (15) | C11—H11 | 0.95 |
O6—C18 | 1.3722 (15) | C12—H12 | 0.95 |
O6—C23 | 1.4363 (15) | C13—H13 | 0.95 |
N1—C26 | 1.137 (2) | C14—H14 | 0.95 |
N2—C28 | 1.1434 (19) | C15—H15A | 0.99 |
C1—C6 | 1.3887 (19) | C15—H15B | 0.99 |
C1—C2 | 1.4087 (16) | C16—H16B | 0.99 |
C2—C3 | 1.3899 (17) | C16—H16A | 0.99 |
C3—C4 | 1.394 (2) | C19—H19 | 0.95 |
C4—C5 | 1.375 (2) | C20—H20 | 0.95 |
C5—C6 | 1.3991 (19) | C21—H21 | 0.95 |
C7—C8 | 1.502 (2) | C22—H22 | 0.95 |
C9—C14 | 1.3872 (19) | C23—H23A | 0.99 |
C9—C10 | 1.4110 (18) | C23—H23B | 0.99 |
C10—C11 | 1.3891 (19) | C24—H24B | 0.99 |
C11—C12 | 1.397 (2) | C24—H24A | 0.99 |
C12—C13 | 1.378 (2) | C25—C26 | 1.450 (2) |
C13—C14 | 1.397 (2) | C25—H25B | 1.00 (2) |
C15—C16 | 1.5082 (17) | C25—H25C | 0.964 (19) |
C17—C22 | 1.3887 (19) | C25—H25A | 0.935 (19) |
C17—C18 | 1.4120 (18) | C27—C28 | 1.458 (2) |
C18—C19 | 1.3882 (17) | C27—H27A | 0.96 (2) |
C19—C20 | 1.396 (2) | C27—H27B | 0.92 (2) |
C20—C21 | 1.378 (2) | C27—H27C | 0.96 (2) |
C21—C22 | 1.3979 (19) | ||
C1—O1—C24 | 115.99 (10) | O3—C8—H8A | 110.01 |
C2—O2—C7 | 113.86 (9) | O3—C8—H8B | 110.02 |
C8—O3—C9 | 116.38 (10) | C7—C8—H8A | 110.04 |
C10—O4—C15 | 118.21 (10) | C7—C8—H8B | 110.03 |
C16—O5—C17 | 116.19 (10) | H8A—C8—H8B | 108.44 |
C18—O6—C23 | 115.26 (9) | C10—C11—H11 | 119.89 |
O1—C1—C2 | 115.59 (11) | C12—C11—H11 | 119.91 |
O1—C1—C6 | 124.89 (10) | C11—C12—H12 | 119.89 |
C2—C1—C6 | 119.52 (11) | C13—C12—H12 | 119.85 |
O2—C2—C1 | 116.55 (10) | C12—C13—H13 | 119.95 |
O2—C2—C3 | 123.88 (10) | C14—C13—H13 | 119.93 |
C1—C2—C3 | 119.57 (12) | C9—C14—H14 | 119.89 |
C2—C3—C4 | 120.42 (12) | C13—C14—H14 | 119.93 |
C3—C4—C5 | 120.03 (13) | O4—C15—H15A | 109.09 |
C4—C5—C6 | 120.31 (14) | O4—C15—H15B | 109.07 |
C1—C6—C5 | 120.16 (12) | C16—C15—H15A | 109.12 |
O2—C7—C8 | 109.81 (10) | C16—C15—H15B | 109.09 |
O3—C8—C7 | 108.30 (10) | H15A—C15—H15B | 107.86 |
O3—C9—C10 | 115.34 (11) | O5—C16—H16A | 110.28 |
O3—C9—C14 | 124.91 (11) | O5—C16—H16B | 110.35 |
C10—C9—C14 | 119.75 (12) | C15—C16—H16A | 110.36 |
O4—C10—C9 | 115.03 (11) | C15—C16—H16B | 110.29 |
O4—C10—C11 | 125.43 (11) | H16A—C16—H16B | 108.61 |
C9—C10—C11 | 119.48 (12) | C18—C19—H19 | 119.90 |
C10—C11—C12 | 120.20 (12) | C20—C19—H19 | 119.94 |
C11—C12—C13 | 120.26 (13) | C19—C20—H20 | 119.67 |
C12—C13—C14 | 120.12 (13) | C21—C20—H20 | 119.71 |
C9—C14—C13 | 120.18 (13) | C20—C21—H21 | 120.01 |
O4—C15—C16 | 112.50 (10) | C22—C21—H21 | 120.08 |
O5—C16—C15 | 106.96 (11) | C17—C22—H22 | 120.02 |
O5—C17—C18 | 115.34 (11) | C21—C22—H22 | 120.01 |
O5—C17—C22 | 124.58 (11) | O6—C23—H23A | 109.70 |
C18—C17—C22 | 120.09 (11) | O6—C23—H23B | 109.73 |
O6—C18—C17 | 116.27 (10) | C24—C23—H23A | 109.74 |
O6—C18—C19 | 124.50 (11) | C24—C23—H23B | 109.71 |
C17—C18—C19 | 119.22 (12) | H23A—C23—H23B | 108.23 |
C18—C19—C20 | 120.16 (12) | O1—C24—H24A | 109.92 |
C19—C20—C21 | 120.61 (12) | O1—C24—H24B | 109.89 |
C20—C21—C22 | 119.91 (13) | C23—C24—H24A | 109.89 |
C17—C22—C21 | 119.98 (12) | C23—C24—H24B | 109.92 |
O6—C23—C24 | 109.71 (9) | H24A—C24—H24B | 108.24 |
O1—C24—C23 | 108.97 (11) | N1—C26—C25 | 178.51 (16) |
C2—C3—H3 | 119.78 | C26—C25—H25A | 109.2 (12) |
C4—C3—H3 | 119.81 | C26—C25—H25B | 108.0 (11) |
C3—C4—H4 | 120.02 | C26—C25—H25C | 107.5 (12) |
C5—C4—H4 | 119.95 | H25A—C25—H25B | 109.3 (16) |
C4—C5—H5 | 119.84 | H25A—C25—H25C | 109.5 (16) |
C6—C5—H5 | 119.86 | H25B—C25—H25C | 113.2 (16) |
C1—C6—H6 | 119.92 | N2—C28—C27 | 179.57 (15) |
C5—C6—H6 | 119.91 | C28—C27—H27A | 108.8 (12) |
O2—C7—H7A | 109.67 | C28—C27—H27B | 109.1 (12) |
O2—C7—H7B | 109.70 | C28—C27—H27C | 108.6 (11) |
C8—C7—H7A | 109.74 | H27A—C27—H27B | 110.9 (17) |
C8—C7—H7B | 109.71 | H27A—C27—H27C | 106.1 (18) |
H7A—C7—H7B | 108.19 | H27B—C27—H27C | 113.1 (18) |
C24—O1—C1—C2 | −169.94 (10) | C3—C4—C5—C6 | −0.5 (2) |
C24—O1—C1—C6 | 10.08 (16) | C4—C5—C6—C1 | 0.4 (2) |
C1—O1—C24—C23 | −176.70 (9) | O2—C7—C8—O3 | 66.12 (12) |
C7—O2—C2—C1 | 159.27 (10) | C10—C9—C14—C13 | 1.11 (17) |
C7—O2—C2—C3 | −20.27 (15) | O3—C9—C14—C13 | −177.99 (11) |
C2—O2—C7—C8 | −171.50 (10) | O3—C9—C10—C11 | 178.11 (10) |
C9—O3—C8—C7 | 173.57 (9) | C14—C9—C10—O4 | −178.29 (10) |
C8—O3—C9—C10 | −179.33 (10) | O3—C9—C10—O4 | 0.90 (14) |
C8—O3—C9—C14 | −0.20 (16) | C14—C9—C10—C11 | −1.07 (16) |
C15—O4—C10—C9 | −169.91 (9) | C9—C10—C11—C12 | 0.16 (17) |
C15—O4—C10—C11 | 13.06 (15) | O4—C10—C11—C12 | 177.07 (10) |
C10—O4—C15—C16 | 76.59 (13) | C10—C11—C12—C13 | 0.71 (18) |
C17—O5—C16—C15 | −172.70 (10) | C11—C12—C13—C14 | −0.67 (19) |
C16—O5—C17—C18 | 167.73 (10) | C12—C13—C14—C9 | −0.24 (18) |
C16—O5—C17—C22 | −12.49 (17) | O4—C15—C16—O5 | 65.78 (13) |
C23—O6—C18—C17 | −172.59 (10) | O5—C17—C18—C19 | −178.18 (11) |
C23—O6—C18—C19 | 6.31 (17) | C22—C17—C18—O6 | −179.01 (11) |
C18—O6—C23—C24 | 178.30 (10) | C22—C17—C18—C19 | 2.03 (18) |
C6—C1—C2—O2 | −179.57 (10) | O5—C17—C18—O6 | 0.79 (16) |
C6—C1—C2—C3 | 0.00 (17) | O5—C17—C22—C21 | 179.25 (12) |
O1—C1—C6—C5 | 179.88 (11) | C18—C17—C22—C21 | −0.98 (19) |
O1—C1—C2—O2 | 0.45 (14) | O6—C18—C19—C20 | 179.76 (12) |
O1—C1—C2—C3 | −180.00 (10) | C17—C18—C19—C20 | −1.37 (19) |
C2—C1—C6—C5 | −0.10 (19) | C18—C19—C20—C21 | −0.3 (2) |
C1—C2—C3—C4 | −0.13 (17) | C19—C20—C21—C22 | 1.4 (2) |
O2—C2—C3—C4 | 179.40 (11) | C20—C21—C22—C17 | −0.7 (2) |
C2—C3—C4—C5 | 0.39 (19) | O6—C23—C24—O1 | −69.35 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1i | 0.95 | 2.50 | 3.293 (2) | 141 |
C16—H16A···N1ii | 0.99 | 2.61 | 3.561 (2) | 162 |
C25—H25B···O1 | 1.00 (2) | 2.52 (2) | 3.455 (2) | 156.0 (14) |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C24H24O6·2C2H3N |
Mr | 490.5 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.109 (2), 10.883 (3), 13.964 (4) |
α, β, γ (°) | 110.16 (2), 96.60 (2), 98.27 (2) |
V (Å3) | 1265.7 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.56 × 0.49 × 0.43 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7849, 6714, 5308 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.115, 1.06 |
No. of reflections | 6714 |
No. of parameters | 343 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.27 |
Computer programs: CAD-4-PC (Enraf-Nonius, 1993), CAD-4-PC, XCAD4 (Harms, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
O1—C1 | 1.3757 (15) | O4—C15 | 1.4346 (15) |
O1—C24 | 1.4335 (15) | O5—C16 | 1.4340 (16) |
O2—C2 | 1.3755 (16) | O5—C17 | 1.3754 (15) |
O2—C7 | 1.4321 (15) | O6—C18 | 1.3722 (15) |
O3—C8 | 1.4296 (15) | O6—C23 | 1.4363 (15) |
O3—C9 | 1.3711 (16) | N1—C26 | 1.137 (2) |
O4—C10 | 1.3746 (16) | N2—C28 | 1.1434 (19) |
N1—C26—C25 | 178.51 (16) | N2—C28—C27 | 179.57 (15) |
C24—O1—C1—C2 | −169.94 (10) | C16—O5—C17—C18 | 167.73 (10) |
C1—O1—C24—C23 | −176.70 (9) | C23—O6—C18—C17 | −172.59 (10) |
C7—O2—C2—C1 | 159.27 (10) | C18—O6—C23—C24 | 178.30 (10) |
C2—O2—C7—C8 | −171.50 (10) | O1—C1—C2—O2 | 0.45 (14) |
C9—O3—C8—C7 | 173.57 (9) | O2—C7—C8—O3 | 66.12 (12) |
C8—O3—C9—C10 | −179.33 (10) | O3—C9—C10—O4 | 0.90 (14) |
C15—O4—C10—C9 | −169.91 (9) | O4—C15—C16—O5 | 65.78 (13) |
C10—O4—C15—C16 | 76.59 (13) | O5—C17—C18—O6 | 0.79 (16) |
C17—O5—C16—C15 | −172.70 (10) | O6—C23—C24—O1 | −69.35 (12) |
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Chemical substitution of the backbone of a crown-ether molecule can dramatically affect its ability to bind specific metal ions (Hay et al., 1996; Sachleben et al., 1996; Tobe et al., 1998, Vögtle & Weber, 1992). As part of our investigations of the steric effects of benzo-substitution on crown ether molecules, we structurally characterized tribenzo-18-crown-6 (Pedersen, 1967; Talanova, et al., 1999).
As illustrated in Fig. 1, the crown ether crystallizes with two molecules of acetonitrile, (I), forming weak hydrogen bonds between the acetonitrile methyl groups and the crown O atoms. The Cmethyl···O separations range from 3.080 (2) (C25···O6) to 3.836 (2) Å (C25···O4) and average about 3.4 Å, which is similar to previously reported results (Sachleben et al., 1997).
The presence of the weakly binding acetonitrile guest molecules suggests that the observed crown-ether conformation could be a relatively low-energy binding mode. A conformer search using computational methods previously described (Bryan et al., 1998) agreed, finding no lower energy conformers. The oxygen dipoles are not oriented towards the center of the crown cavity, inhibiting efficient coordination of a guest species in the center of the cavity. Moreover, only four (O3—O6) of the six dipoles point out one face of the crown cavity, weakening binding to a particular face. Such divergence of the donor groups suggests that this conformation will not efficiently bind a cation (Hay & Hancock, 2001). The conformation of the crown ring can be described in terms of the torsion angles around ring (Dale, 1980), where g and a represent gauche and anti, respectively, 0 represents an aromatic O—C—C—O torsion angle, and a superscript following the g indicates the sign of the angle. Starting with the O1—C1—C2—O2 angle, it is 0aa g+aa 0ag+ g+aa 0aa g-aa, where the spaces indicate O-atom locations.
There are few significant intermolecular interactions in this structure. No π-stacking of arene rings is observed, but one edge–face arene interaction is apparent (C17—C20···C1i—C6i). Two C—H···π interactions are also observed, H7B···C9ii—14ii and H24A···C17iii—22iii [symmetry codes: (i) -x, -y, 1 - z; (ii) -x, -y, -z; (iii) 1 - x, -y, 1 - z].