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The structures of three syn-1,3-dialkoxy­thia­calix[4]arenes with unusual conformations in the solid state are reported. The pinched cone conformation of syn-22,42-dihydroxy-12,32-bis­(prop-2-enyl­oxy)thia­calix[4]arene, C30H24O4S4, (3a), is stabilized by two intra­molecular hydrogen bonds, remarkably formed from both OH groups to the same ether O atom. In syn-22,42-dihydroxy-15,25,35,45-tetra­nitro-12,32-bis­(prop-2-enyl­oxy)thia­calix[4]arene acetone disolvate, C30H20N4O12S4·2C3H6O, (3b1), the mol­ecule is found in the 1,3-alternate conformation. The crystallographic C2 symmetry is due to a twofold rotation axis running through the centre of the calixarene ring. The hydroxy groups cannot form intra­molecular hydrogen bonds as in (3a) and both are bonded to an acetone solvent mol­ecule. The mol­ecule of the pseudo-polymorph of (3b1) in which the same compound crystallized without any solvent, viz. (3b2), is located on a crystallographic mirror plane. Only one of the two hydroxy groups forms a hydrogen bond, and this is with a nitro group of a neighbouring mol­ecule as acceptor. Mol­ecular mechanics calculations for syn-1,3-diethers suggest a preference of the 1,3-alternate over the usual cone conformation for thia­calix[4]arene versus calix[4]arene and for para-nitro versus para-H derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106011243/av3005sup1.cif
Contains datablocks 3a, 3b1, 3b2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106011243/av30053asup2.hkl
Contains datablock boeh43

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106011243/av30053b1sup3.hkl
Contains datablock boeh42

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106011243/av30053b2sup4.hkl
Contains datablock boeh48

CCDC references: 609551; 609552; 609553

Comment top

In principle, thiacalix[4]arenes (1) can undergo analogous chemical modifications as calix[4]arenes (2) on their wide rim (e.g. transbutylation and electrophilic substitutions) and on their narrow rim (e.g. O-alkylation) (Böhmer, 1995). Subtle differences are found, however, in both cases. Ether residues introduced to (1) must be larger than propyl (Lang et al., 1999; Lhotak, 2004) [which is sufficient for (2) (Böhmer, 1995)] to prevent a rotation through the annulus, and the introduction of four ether groups leads usually to derivatives in which the 1,3-alternate conformation is fixed (Lhotak et al., 1998; Lhotak, 2004). Derivatives in the cone conformation are only formed with alkylating agents of the type X—CH2—C(O)—R (Iki et al., 1998; Akdas et al., 1999) or X—CH2—Ar (Yamato et al., 2002) in the presence of sodium cations. For both calix[4]arenes, 1,3-diethers with a syn-orientation of the ether residues are easily obtained with a variety of alkylating agents. The conformational analysis of thiacalixarenes and their derivatives in solution is complicated by the fact, that the spectroscopic information given by methylene H atoms is not available in the 1H NMR spectra. The 13C chemical shift of the methylene bridges, often useful for the conformational assignment (Jaime et al., 1991) is also lacking. This makes conformational information from the crystalline state more important.

All five X-ray structures reported for syn-1,3-diether derivatives (3) (Dudic et al., 2003, 2004; Clemente, 2003; Bhalla et al. 2004) show the compounds in the cone conformation. 103 structures of syn-1,3-diethers (4) (metal complexes are not included) are found in the Cambridge Structural Database (CSD version 5.27 plus one update; Mogul Version 1.1; Allen, 2002), among which only one example has a 1,3-alternate conformation (Simaan et al., 2003) while the rest assume the (pinched) cone conformation. (From 15 structures of syn-1,3-diesters two partial cone and one 1,3-alternate conformation are found.) The reason for this disparity is usually searched for in the stabilization of the cone conformation by intramolecular hydrogen bonds between the phenol hydroxy groups and the adjacent ether O atoms. From further O-alkylation products it can be deduced, however, that the molecules can assume the partial cone or the 1,3-alternate conformation by passing of the OH groups through the annulus. We recently prepared (Böhmer & Kasyan, 2006) the 1,3-diallylethers (3a) and (3b) and report their crystal structures in the following. For (3b), which was crystallized from different solvents, two pseudo-polymorphs, (3b1) and (3b2), were obtained.

Perspective views of (3a), (3b1) and (3b2) are shown in Figs. 1–3. Bond lengths and angles can be regarded as normal (CSD).

Single crystals of (3a) were obtained from acetonitrile. As expected, the molecule is found in a pinched cone conformation, with the ether units bent towards the cavity and the phenol units bent outwards. In Table 4, the angles between the mean planes through the aromatic rings and the reference/mean plane defined by the four S atoms are listed and used to characterize the conformation. One of these angles is even smaller than 90°, which means that this plane is oriented `into' the cavity, while the opposite one is oriented outwards. Thus, the planes of the ether substituted phenyl rings are almost coplanar [6.53 (8)°], a situation also found for other 1,3-diethers of (1). The packing of the molecules is obviously determined by ππ stacking of aromatic units. Chains of molecules with alternating orientation extend along the c axis (Fig. 4) with aryl–aryl contacts between the phenylether rings [the distance between the centroids of the aromatic rings C21–C26 and C41iii–C46iii is 3.980 Å; symmetry code: (iii) x, 3/2 − y, 1/2 + z], while along the a axis contacts between the phenol units exist [the distance between the centroids of the aromatic rings C11–C16 and C31iv–C36iv is 4.204 Å; symmetry operator: (ii) −1 + x, y, z]. It is remarkable that both OH groups form hydrogen bonds to the same ether O atom.

Single crystals of (3b) were obtained from acetone and from ethanol/methylene chloride, resulting in two different crystal structures, (3b1) and (3b2), respectively. The crystals of (3b1) include two molecules of acetone per calixarene molecule. Surprisingly, and in contrast to (3a), here the molecules assume a `perfect' 1,3-alternate conformation with crystallographic twofold symmetry (see Fig. 2).

Although the quality of (3b2) was not as good, the crystal structure clearly shows the molecules, which are located on a crystallographic mirror plane, in the 1,3-alternate conformation again. Small differences in shape are evident from the values collected in Table 1 and the least-squares fit (Fig. 5). However, the overall conformation of (3b1) and (3b2) is very similar.

In contrast to (3a), interactions via ππ stacking are not pronounced in the structures of either (3b1) or (3b2). For (3b1), molecular columns of head-to-tail-oriented molecules along the c axis are found. Subsequent molecules are alternately turned by 72.8° around the column axis. As seen in Fig. 6, adjacent columns have the opposite direction.

Fig. 7 suggests a similar arrangement into columns along the a axis for (3b2). However, subsequent molecules are not directly stacked above one another, but shifted by c/2 with respect to each other.

The structures of (3b1) and (3b2) are the first examples in which a derivative of type 3 is found in the 1,3-alternate conformation (see above). The question arises why the molecule does not assume a cone conformation, which should be stabilized by intramolecular hydrogen bonds. For the 1,3-diether (Simaan et al., 2003) a favourable packing was assumed as the reason for the 1,3-alternate conformation. In the case of (3b1) two intermolecular hydrogen bonds between calixarene molecules and solvent molecules are found in the crystal lattice and in the case of (3b2) one hydrogen bond to an adjacent molecule. However, it seems likely that the reason must be searched for also in the molecule itself.

Therefore, molecular mechanics calculations using the MMFF94 force field (Halgren, 1990) have been performed to assess the energy differences of the cone and 1,3-alternate conformations of the syn-1,3-diethers of `classical' and of thiacalix[4]arenes. The results of these conformational analyses are summarized in Table 5.

The calculations suggest a different conformational behaviour for the two classes of compounds. In agreement with the experimental observations, the calix[4]arene derivatives prefer the cone conformation, which is stabilized over the 1,3-alternate form by hydrogen bonding [(IVa)–(IVc)]. In contrast, the syn-1,3-diethers of thiacalixarenes are predicted to exist predominantly in the 1,3-alternate arrangement [(IIIa)–(IIIc)]. This results mainly from unfavourable bonding contributions to the steric energy of the cone form, which are, however, in part compensated by favourable non-bonding terms due to hydrogen bonding for (IIIb) and (IIIc). For (IIIa), the 1,3-alternate conformer is also favoured by the non-bonding term, which may arise from the compensation of the dipole moments in this form.

Since it may be hypothesized that the distorted pinched cone conformation found in the crystal structure of (3a) is the result of packing forces due to ππ interactions we have optimized this structure with the help of the MMFF94 force field. The resulting energy minimized conformer is very similar to the crystal structure (the r.m.s. deviation of the calixarene C atoms is 0.18 Å), indicating that this pinched cone form is indeed an energy minimum. However, its energy is 5.5 kcal mol−1 above the global minimum (which corresponds to the 1,3-alternate arrangement) suggesting that the packing forces contribute to the stabilization of this conformation in the crystal structure.

In conclusionhe conformation of (thia)calix[4]arenes and their derivatives is determined by various competing factors. The thiacalix[4]arene skeleton obviously prefers the 1,3-alternate conformation. Thus, tetraethers are usually obtained as 1,3-alternate conformers from thiacalixarenes and as cone conformers from methylene-bridged calixarenes. A circular array of intramolecular hydrogen bonds between hydroxy groups explains the preference of the cone conformation of the tetrahydroxy compounds in both cases. The competition between intramolecular hydrogen bonds (stabilizing the cone conformation) and compensation of dipole moments (in the 1,3-alternate conformation) explains why (3a) is found in the cone conformation and (3b) in the 1,3-alternate conformation. 1,3-Diethers of calix[4]arenes, however, are (nearly) always found in the cone conformation.

Experimental top

Compounds (3a) and (3b) were obtained under standard conditions, refluxing thiacalix[4]arene [(1), R = H] or tetranitrothiacalix[4]arene [(1), R = NO2] with an excess of allylbromide and sodium carbonate in acetone or acetonitrile, respectively. Details will be published in a wider context (Böhmer & Kasyan, 2006)

Refinement top

For all compounds, H atoms were located in a difference electron density map, and for (3a) and (3b1) the hydroxy H atoms were refined isotropically. All other H atoms were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl,O)] using a riding model, with C—H ranging from 0.95 to 0.99 Å and, for (3b2), O—H = 0.84 Å. For (3a), one terminal atom of a propenoxy chain is disordered over two positions with site occupation factors of 0.556 (7) and 0.444 (7). For (3b2), one terminal atom of a propenoxy chain is disordered over two positions with site occupation factors of 0.726 (15) and 0.274 (15); these two atoms were refined isotropically. The two hydroxy H atoms of (3b2) are disordered over two equally occupied positions. The conformational search of (III)/(IV) was performed with the Randomsearch module of the Sybyl program package (TRIPOS Associates, 1996). Starting structures were generated manually from the 1,3-alternate and cone conformers of a previously calculated p-tert-butylcalix[4]arene. All Ar—X bonds and the single bonds of the ether groups were chosen as rotatable. A maximum of 2000 cycles of random perturbation of the dihedral angles was allowed using an energy cutoff of 20 kcal mol−1 above the actual minimum. A constant dielectric with ε = 1 was used. The resulting structures were minimized with the MMFF94 force field, which is included in the Sybyl program, until the r.m.s. energy gradient was less than 10−3 kcal mol−1 Å−1. Please check; text rearranged to avoid repetition of similar methods.

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A perspective view of (3a), with the atom numbering. Displacement ellipsoids are shown at the 50% probability level, and atoms of the minor occupied disordered component have been omitted for clarity. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. A perspective view of (3b1), with the atom numbering. Displacement ellipsoids are shown at the 50% probability level. Hydrogen bonds are shown as dashed lines. Non-labelled atoms are generated by the symmetry operator (−x + 3/2, −y + 3/2, z).
[Figure 3] Fig. 3. A perspective view of (3b2) with the atom numbering. Displacement ellipsoids are shown at the 30% probability level, and H atoms bonded to C atoms have been omitted for clarity. Only one of the disordered atoms is shown. Non-labelled atoms are generated by the symmetry operator (x, −y + 3/2, z).
[Figure 4] Fig. 4. A packing diagram of (3a), viewed along the a axis; atoms of the minor occupied disordered component have been omitted for clarity.
[Figure 5] Fig. 5. A least-squares fit of (3b1) and (3b2); only the S atoms are fitted (the r.m.s. deviation is 0.170 Å).
[Figure 6] Fig. 6. A packing diagram of (3b1), viewed along the a axis. Hydrogen bonds are indicated as dashed lines.
[Figure 7] Fig. 7. A packing diagram of (3b2), viewed along the c axis; atoms of the minor occupied disordered component have been omitted for clarity. Hydrogen bonds are indicated as dashed lines. R
(3a) syn-22,42-dihydroxy-12,32-bis(prop-2-enoxy)thiacalix[4]arene top
Crystal data top
C30H24O4S4F(000) = 1200
Mr = 576.73Dx = 1.374 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 33932 reflections
a = 9.2591 (8) Åθ = 2.7–27.3°
b = 18.5282 (13) ŵ = 0.38 mm1
c = 16.7729 (17) ÅT = 173 K
β = 104.297 (7)°Rod, colourless
V = 2788.3 (4) Å30.36 × 0.12 × 0.10 mm
Z = 4
Data collection top
STOE IPDS-II two-circle-
diffractometer
6073 independent reflections
Radiation source: fine-focus sealed tube4194 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
ω scansθmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1111
Tmin = 0.877, Tmax = 0.963k = 2123
39745 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0693P)2]
where P = (Fo2 + 2Fc2)/3
6073 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C30H24O4S4V = 2788.3 (4) Å3
Mr = 576.73Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2591 (8) ŵ = 0.38 mm1
b = 18.5282 (13) ÅT = 173 K
c = 16.7729 (17) Å0.36 × 0.12 × 0.10 mm
β = 104.297 (7)°
Data collection top
STOE IPDS-II two-circle-
diffractometer
6073 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
4194 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.963Rint = 0.096
39745 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.38 e Å3
6073 reflectionsΔρmin = 0.33 e Å3
361 parameters
Special details top

Experimental.

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.24963 (6)0.68706 (3)0.38644 (4)0.04105 (16)
S20.26817 (6)0.69039 (3)0.71811 (4)0.04039 (16)
S30.88343 (6)0.68920 (3)0.79256 (4)0.04095 (16)
S40.86509 (6)0.69735 (3)0.45934 (4)0.03936 (16)
O120.18974 (16)0.74545 (8)0.54395 (11)0.0405 (4)
O220.56650 (18)0.72634 (9)0.69643 (11)0.0393 (4)
H220.651 (4)0.7411 (17)0.6948 (19)0.065 (10)*
O320.81214 (15)0.75264 (8)0.62101 (10)0.0372 (4)
O420.55494 (18)0.72633 (9)0.48142 (11)0.0398 (4)
H420.640 (4)0.7383 (18)0.503 (2)0.068 (10)*
C110.2786 (2)0.64184 (12)0.48315 (14)0.0352 (5)
C120.2533 (2)0.67742 (12)0.55201 (14)0.0338 (5)
C130.2853 (2)0.64265 (12)0.62839 (14)0.0345 (5)
C140.3357 (2)0.57139 (12)0.63478 (15)0.0382 (5)
H140.35430.54720.68630.046*
C150.3587 (3)0.53584 (13)0.56632 (15)0.0404 (5)
H150.39350.48740.57100.048*
C160.3310 (2)0.57059 (12)0.49119 (15)0.0382 (5)
H160.34770.54600.44460.046*
C210.4426 (2)0.66360 (13)0.78339 (15)0.0370 (5)
C220.5757 (2)0.68434 (12)0.76356 (14)0.0343 (5)
C230.7125 (2)0.65989 (13)0.81310 (14)0.0365 (5)
C240.7149 (3)0.61794 (15)0.88217 (16)0.0470 (6)
H240.80760.60190.91560.056*
C250.5837 (3)0.59919 (16)0.90281 (16)0.0508 (6)
H250.58630.57110.95060.061*
C260.4473 (3)0.62203 (14)0.85253 (16)0.0452 (6)
H260.35700.60890.86600.054*
C310.8846 (2)0.64330 (12)0.69843 (14)0.0348 (5)
C320.8620 (2)0.68164 (11)0.62444 (14)0.0330 (5)
C330.8792 (2)0.64761 (12)0.55298 (14)0.0343 (5)
C340.9148 (2)0.57400 (12)0.55567 (15)0.0384 (5)
H340.92680.55040.50740.046*
C350.9325 (3)0.53554 (13)0.62801 (15)0.0423 (6)
H350.95390.48540.62900.051*
C360.9192 (2)0.57008 (13)0.69934 (15)0.0397 (5)
H360.93390.54360.74920.048*
C410.6922 (2)0.66545 (12)0.39629 (14)0.0356 (5)
C420.5580 (2)0.68578 (12)0.41466 (14)0.0329 (5)
C430.4214 (2)0.66319 (13)0.36339 (14)0.0368 (5)
C440.4211 (3)0.62283 (14)0.29314 (15)0.0442 (6)
H440.32920.60720.25840.053*
C450.5550 (3)0.60521 (15)0.27333 (16)0.0475 (6)
H450.55360.57910.22440.057*
C460.6899 (3)0.62588 (13)0.32529 (15)0.0422 (6)
H460.78090.61300.31240.051*
C1210.2922 (3)0.80527 (12)0.55023 (18)0.0443 (6)
H12A0.37300.79330.52330.053*
H12B0.33730.81710.60860.053*
C1220.2020 (3)0.86751 (15)0.50765 (19)0.0535 (7)
H1220.14100.85940.45390.064*
C1230.2007 (4)0.93075 (18)0.5380 (3)0.0797 (10)
H12C0.26020.94100.59160.096*
H12D0.14030.96750.50700.096*
C3210.9307 (3)0.80636 (13)0.63865 (19)0.0478 (6)
H32A0.99510.80080.59990.057*
H32B0.99290.79980.69530.057*
C3220.8621 (4)0.87949 (15)0.62979 (19)0.0574 (7)
H32C0.93340.91720.63580.069*0.556 (7)
H32D0.78300.88460.58180.069*0.444 (7)
C3230.7363 (6)0.9011 (3)0.6167 (3)0.0492 (15)0.556 (7)
H32E0.71510.94480.64110.059*0.556 (7)
H32F0.65780.87450.58190.059*0.556 (7)
C3240.8848 (9)0.9308 (4)0.6688 (5)0.074 (3)0.444 (7)
H32G0.80480.96190.67200.089*0.444 (7)
H32H0.98370.94230.69810.089*0.444 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0252 (3)0.0520 (4)0.0427 (3)0.0049 (2)0.0022 (2)0.0042 (3)
S20.0255 (3)0.0483 (4)0.0482 (3)0.0011 (2)0.0107 (2)0.0096 (3)
S30.0262 (3)0.0522 (4)0.0416 (3)0.0031 (2)0.0028 (2)0.0092 (3)
S40.0259 (3)0.0470 (3)0.0467 (3)0.0028 (2)0.0119 (2)0.0089 (3)
O120.0239 (7)0.0376 (9)0.0595 (10)0.0052 (6)0.0095 (7)0.0012 (8)
O220.0252 (8)0.0431 (9)0.0486 (10)0.0005 (7)0.0071 (7)0.0067 (7)
O320.0245 (7)0.0332 (8)0.0549 (10)0.0036 (6)0.0119 (7)0.0004 (7)
O420.0247 (8)0.0454 (10)0.0488 (10)0.0018 (7)0.0081 (7)0.0083 (8)
C110.0215 (10)0.0402 (12)0.0421 (12)0.0042 (8)0.0045 (9)0.0020 (10)
C120.0170 (9)0.0360 (11)0.0466 (13)0.0005 (8)0.0045 (9)0.0020 (10)
C130.0222 (10)0.0364 (12)0.0447 (13)0.0039 (8)0.0082 (9)0.0054 (10)
C140.0334 (11)0.0370 (12)0.0432 (13)0.0038 (9)0.0075 (10)0.0007 (10)
C150.0374 (12)0.0331 (12)0.0508 (14)0.0026 (9)0.0109 (10)0.0028 (10)
C160.0332 (11)0.0368 (12)0.0446 (13)0.0048 (9)0.0092 (10)0.0076 (10)
C210.0300 (11)0.0410 (12)0.0404 (13)0.0023 (9)0.0095 (9)0.0098 (10)
C220.0325 (11)0.0319 (11)0.0384 (12)0.0004 (9)0.0087 (9)0.0055 (9)
C230.0291 (10)0.0412 (13)0.0374 (12)0.0010 (9)0.0053 (9)0.0073 (10)
C240.0433 (13)0.0540 (15)0.0401 (13)0.0051 (11)0.0036 (11)0.0021 (12)
C250.0534 (15)0.0609 (17)0.0384 (14)0.0005 (13)0.0120 (12)0.0034 (12)
C260.0417 (13)0.0528 (15)0.0449 (14)0.0050 (11)0.0177 (11)0.0047 (12)
C310.0226 (9)0.0411 (12)0.0387 (12)0.0021 (9)0.0038 (8)0.0035 (10)
C320.0178 (9)0.0322 (11)0.0483 (13)0.0005 (8)0.0068 (9)0.0006 (10)
C330.0231 (9)0.0382 (12)0.0413 (12)0.0034 (8)0.0071 (9)0.0041 (10)
C340.0295 (11)0.0379 (12)0.0452 (13)0.0028 (9)0.0044 (9)0.0048 (10)
C350.0375 (12)0.0345 (12)0.0496 (14)0.0039 (9)0.0011 (10)0.0017 (10)
C360.0328 (11)0.0382 (13)0.0438 (13)0.0006 (9)0.0013 (10)0.0044 (10)
C410.0325 (11)0.0365 (12)0.0387 (12)0.0045 (9)0.0104 (9)0.0095 (9)
C420.0293 (10)0.0328 (11)0.0363 (12)0.0047 (8)0.0072 (9)0.0048 (9)
C430.0314 (11)0.0396 (12)0.0381 (12)0.0022 (9)0.0058 (9)0.0056 (10)
C440.0407 (13)0.0528 (15)0.0355 (12)0.0020 (11)0.0025 (10)0.0052 (11)
C450.0513 (14)0.0562 (16)0.0356 (13)0.0079 (12)0.0119 (11)0.0016 (11)
C460.0424 (13)0.0476 (14)0.0389 (13)0.0101 (11)0.0142 (10)0.0096 (11)
C1210.0360 (12)0.0332 (12)0.0666 (17)0.0032 (9)0.0182 (12)0.0011 (11)
C1220.0511 (15)0.0497 (16)0.0650 (18)0.0026 (12)0.0243 (13)0.0076 (13)
C1230.089 (2)0.0504 (19)0.109 (3)0.0179 (17)0.042 (2)0.0162 (19)
C3210.0370 (12)0.0350 (13)0.0776 (19)0.0059 (10)0.0261 (13)0.0051 (12)
C3220.078 (2)0.0386 (15)0.0649 (19)0.0070 (14)0.0346 (16)0.0064 (13)
C3230.060 (3)0.044 (3)0.049 (3)0.016 (2)0.023 (2)0.001 (2)
C3240.073 (5)0.045 (4)0.116 (7)0.017 (3)0.044 (5)0.039 (4)
Geometric parameters (Å, º) top
S1—C431.783 (2)C31—C361.393 (3)
S1—C111.786 (2)C31—C321.400 (3)
C11—C121.399 (3)C32—O321.391 (3)
C11—C161.401 (3)C32—C331.398 (3)
C12—O121.384 (3)C33—C341.401 (3)
C12—C131.399 (3)C33—S41.798 (2)
C13—C141.396 (3)C34—C351.382 (3)
C13—S21.786 (2)C34—H340.9500
C14—C151.385 (3)C35—C361.389 (3)
C14—H140.9500C35—H350.9500
C15—C161.382 (3)C36—H360.9500
C15—H150.9500O32—C3211.457 (3)
C16—H160.9500C321—C3221.488 (4)
O12—C1211.446 (3)C321—H32A0.9900
C121—C1221.498 (4)C321—H32B0.9900
C121—H12A0.9900C322—C3241.144 (7)
C121—H12B0.9900C322—C3231.200 (5)
C122—C1231.279 (4)C322—H32C0.9500
C122—H1220.9500C322—H32D0.9500
C123—H12C0.9500C323—H32E0.9500
C123—H12D0.9500C323—H32F0.9500
S2—C211.783 (2)C324—H32G0.9500
C21—C261.384 (4)C324—H32H0.9500
C21—C221.407 (3)S4—C411.787 (2)
C22—O221.354 (3)C41—C461.394 (3)
C22—C231.407 (3)C41—C421.404 (3)
C23—C241.391 (4)C42—O421.355 (3)
C23—S31.786 (2)C42—C431.406 (3)
C24—C251.387 (4)C43—C441.395 (3)
C24—H240.9500C44—C451.398 (4)
C25—C261.400 (4)C44—H440.9500
C25—H250.9500C45—C461.389 (4)
C26—H260.9500C45—H450.9500
O22—H220.83 (3)C46—H460.9500
S3—C311.796 (2)O42—H420.82 (3)
C43—S1—C1197.97 (10)O32—C32—C31119.5 (2)
C12—C11—C16119.3 (2)C33—C32—C31120.5 (2)
C12—C11—S1120.70 (17)C32—C33—C34119.2 (2)
C16—C11—S1120.00 (18)C32—C33—S4121.25 (17)
O12—C12—C13119.9 (2)C34—C33—S4119.54 (18)
O12—C12—C11120.2 (2)C35—C34—C33120.4 (2)
C13—C12—C11119.9 (2)C35—C34—H34119.8
C14—C13—C12119.8 (2)C33—C34—H34119.8
C14—C13—S2120.09 (18)C34—C35—C36120.2 (2)
C12—C13—S2120.05 (17)C34—C35—H35119.9
C15—C14—C13120.2 (2)C36—C35—H35119.9
C15—C14—H14119.9C35—C36—C31120.6 (2)
C13—C14—H14119.9C35—C36—H36119.7
C16—C15—C14120.2 (2)C31—C36—H36119.7
C16—C15—H15119.9C32—O32—C321114.35 (16)
C14—C15—H15119.9O32—C321—C322108.7 (2)
C15—C16—C11120.6 (2)O32—C321—H32A110.0
C15—C16—H16119.7C322—C321—H32A110.0
C11—C16—H16119.7O32—C321—H32B110.0
C12—O12—C121115.83 (16)C322—C321—H32B110.0
O12—C121—C122106.1 (2)H32A—C321—H32B108.3
O12—C121—H12A110.5C324—C322—C32382.0 (5)
C122—C121—H12A110.5C324—C322—C321133.3 (6)
O12—C121—H12B110.5C323—C322—C321133.9 (4)
C122—C121—H12B110.5C324—C322—H32C45.7
H12A—C121—H12B108.7C323—C322—H32C113.1
C123—C122—C121125.1 (3)C321—C322—H32C113.1
C123—C122—H122117.5C324—C322—H32D113.4
C121—C122—H122117.5C323—C322—H32D45.7
C122—C123—H12C120.0C321—C322—H32D113.4
C122—C123—H12D120.0H32C—C322—H32D112.7
H12C—C123—H12D120.0C322—C323—H32E120.0
C21—S2—C1397.13 (10)C322—C323—H32F120.0
C26—C21—C22120.1 (2)H32E—C323—H32F120.0
C26—C21—S2120.38 (18)C322—C324—H32G120.0
C22—C21—S2119.49 (18)C322—C324—H32H120.0
O22—C22—C23122.6 (2)H32G—C324—H32H120.0
O22—C22—C21118.3 (2)C41—S4—C33102.06 (10)
C23—C22—C21119.1 (2)C46—C41—C42120.1 (2)
C24—C23—C22119.9 (2)C46—C41—S4120.10 (17)
C24—C23—S3119.87 (17)C42—C41—S4119.58 (18)
C22—C23—S3119.97 (18)O42—C42—C41122.03 (19)
C25—C24—C23120.9 (2)O42—C42—C43118.15 (19)
C25—C24—H24119.6C41—C42—C43119.8 (2)
C23—C24—H24119.6C44—C43—C42119.3 (2)
C24—C25—C26119.3 (2)C44—C43—S1120.04 (17)
C24—C25—H25120.3C42—C43—S1120.61 (18)
C26—C25—H25120.3C43—C44—C45120.6 (2)
C21—C26—C25120.7 (2)C43—C44—H44119.7
C21—C26—H26119.7C45—C44—H44119.7
C25—C26—H26119.7C46—C45—C44119.9 (2)
C22—O22—H22110 (2)C46—C45—H45120.0
C23—S3—C31102.92 (10)C44—C45—H45120.0
C36—C31—C32119.2 (2)C45—C46—C41120.1 (2)
C36—C31—S3120.19 (18)C45—C46—H46119.9
C32—C31—S3120.46 (17)C41—C46—H46119.9
O32—C32—C33119.9 (2)C42—O42—H42108 (2)
C43—S1—C11—C12131.62 (17)C23—S3—C31—C32108.48 (18)
C43—S1—C11—C1646.67 (19)C36—C31—C32—O32173.26 (18)
C16—C11—C12—O12174.53 (18)S3—C31—C32—O3211.6 (3)
S1—C11—C12—O127.2 (3)C36—C31—C32—C332.3 (3)
C16—C11—C12—C132.2 (3)S3—C31—C32—C33172.85 (16)
S1—C11—C12—C13176.06 (15)O32—C32—C33—C34173.53 (18)
O12—C12—C13—C14173.74 (18)C31—C32—C33—C342.0 (3)
C11—C12—C13—C143.0 (3)O32—C32—C33—S49.3 (3)
O12—C12—C13—S28.5 (3)C31—C32—C33—S4175.10 (16)
C11—C12—C13—S2174.71 (15)C32—C33—C34—C350.0 (3)
C12—C13—C14—C152.1 (3)S4—C33—C34—C35177.20 (17)
S2—C13—C14—C15175.65 (17)C33—C34—C35—C361.8 (3)
C13—C14—C15—C160.3 (3)C34—C35—C36—C311.5 (3)
C14—C15—C16—C110.4 (3)C32—C31—C36—C350.6 (3)
C12—C11—C16—C150.5 (3)S3—C31—C36—C35174.62 (17)
S1—C11—C16—C15177.81 (17)C33—C32—O32—C32192.7 (2)
C13—C12—O12—C12196.1 (2)C31—C32—O32—C32191.7 (2)
C11—C12—O12—C12187.2 (2)C32—O32—C321—C322177.9 (2)
C12—O12—C121—C122157.9 (2)O32—C321—C322—C324135.0 (6)
O12—C121—C122—C123129.6 (3)O32—C321—C322—C3235.1 (6)
C14—C13—S2—C2144.94 (19)C32—C33—S4—C41109.04 (18)
C12—C13—S2—C21132.79 (17)C34—C33—S4—C4173.84 (19)
C13—S2—C21—C26116.1 (2)C33—S4—C41—C46114.77 (19)
C13—S2—C21—C2263.1 (2)C33—S4—C41—C4270.8 (2)
C26—C21—C22—O22178.6 (2)C46—C41—C42—O42177.7 (2)
S2—C21—C22—O222.2 (3)S4—C41—C42—O423.2 (3)
C26—C21—C22—C232.4 (3)C46—C41—C42—C433.0 (3)
S2—C21—C22—C23176.81 (17)S4—C41—C42—C43177.49 (17)
O22—C22—C23—C24178.8 (2)O42—C42—C43—C44178.5 (2)
C21—C22—C23—C242.2 (3)C41—C42—C43—C442.2 (3)
O22—C22—C23—S34.3 (3)O42—C42—C43—S10.4 (3)
C21—C22—C23—S3176.72 (17)C41—C42—C43—S1178.94 (17)
C22—C23—C24—C250.5 (4)C11—S1—C43—C44118.9 (2)
S3—C23—C24—C25175.0 (2)C11—S1—C43—C4262.2 (2)
C23—C24—C25—C261.0 (4)C42—C43—C44—C450.4 (4)
C22—C21—C26—C251.0 (4)S1—C43—C44—C45178.5 (2)
S2—C21—C26—C25178.3 (2)C43—C44—C45—C462.2 (4)
C24—C25—C26—C210.8 (4)C44—C45—C46—C411.3 (4)
C24—C23—S3—C31114.8 (2)C42—C41—C46—C451.3 (3)
C22—C23—S3—C3170.7 (2)S4—C41—C46—C45175.69 (19)
C23—S3—C31—C3676.40 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O320.83 (3)2.17 (3)2.904 (2)146 (3)
O42—H42···O320.82 (3)2.23 (3)2.939 (2)146 (3)
(3b1) syn-22,42-dihydroxy-15,25,35,45-tetranitro-12,32– bis(prop-2-enoxy)thiacalix[4]arene acetone disolvate top
Crystal data top
C30H20N4O12S4·2C3H6OF(000) = 1808
Mr = 872.90Dx = 1.447 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 60450 reflections
a = 8.8760 (3) Åθ = 2.7–27.8°
b = 17.3100 (5) ŵ = 0.31 mm1
c = 26.0798 (10) ÅT = 173 K
V = 4007.0 (2) Å3Plate, colourless
Z = 40.42 × 0.37 × 0.19 mm
Data collection top
STOE IPDS-II two-circle-
diffractometer
4617 independent reflections
Radiation source: fine-focus sealed tube4227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ω scansθmax = 27.7°, θmin = 2.8°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1111
Tmin = 0.881, Tmax = 0.944k = 2222
56923 measured reflectionsl = 3433
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0372P)2 + 2.018P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4617 reflectionsΔρmax = 0.31 e Å3
267 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (3)
Crystal data top
C30H20N4O12S4·2C3H6OV = 4007.0 (2) Å3
Mr = 872.90Z = 4
Orthorhombic, PccnMo Kα radiation
a = 8.8760 (3) ŵ = 0.31 mm1
b = 17.3100 (5) ÅT = 173 K
c = 26.0798 (10) Å0.42 × 0.37 × 0.19 mm
Data collection top
STOE IPDS-II two-circle-
diffractometer
4617 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
4227 reflections with I > 2σ(I)
Tmin = 0.881, Tmax = 0.944Rint = 0.067
56923 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.31 e Å3
4617 reflectionsΔρmin = 0.20 e Å3
267 parameters
Special details top

Experimental.

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.10374 (4)0.616317 (19)0.384606 (13)0.02121 (9)
S20.48375 (4)0.566071 (19)0.371849 (13)0.02109 (9)
O30.34739 (15)0.63844 (7)0.25405 (4)0.0372 (3)
O120.78776 (11)0.59610 (5)0.42519 (4)0.0212 (2)
O220.44018 (12)0.73365 (6)0.33263 (4)0.0268 (2)
H220.418 (3)0.6928 (14)0.3145 (9)0.050 (6)*
O1510.71047 (14)0.55879 (9)0.18687 (5)0.0437 (3)
O1520.95137 (14)0.58156 (7)0.19102 (4)0.0363 (3)
O2510.43113 (19)0.64501 (8)0.56568 (5)0.0489 (3)
O2520.4387 (3)0.76954 (8)0.57074 (5)0.0714 (6)
N150.82703 (15)0.57261 (7)0.21097 (5)0.0269 (3)
N250.43783 (18)0.70927 (8)0.54589 (5)0.0363 (3)
C30.38755 (18)0.66006 (8)0.21168 (6)0.0280 (3)
C110.93641 (14)0.60122 (7)0.34818 (5)0.0191 (3)
C120.79616 (14)0.59182 (7)0.37283 (5)0.0179 (2)
C130.66501 (14)0.57936 (7)0.34330 (5)0.0187 (3)
C140.67667 (15)0.57194 (7)0.29021 (5)0.0212 (3)
H140.58970.56230.27000.025*
C150.81750 (16)0.57880 (7)0.26735 (5)0.0213 (3)
C160.94793 (15)0.59462 (7)0.29504 (5)0.0212 (3)
H161.04210.60070.27820.025*
C210.46619 (14)0.65281 (7)0.40820 (5)0.0190 (2)
C220.44599 (14)0.72503 (8)0.38356 (5)0.0188 (3)
C230.43351 (14)0.79279 (7)0.41390 (5)0.0189 (2)
C240.43420 (15)0.78768 (8)0.46700 (5)0.0222 (3)
H240.42770.83300.48740.027*
C250.44452 (16)0.71518 (8)0.48995 (5)0.0239 (3)
C260.46214 (15)0.64789 (8)0.46137 (5)0.0213 (3)
H260.47130.59930.47800.026*
C310.4947 (3)0.72639 (11)0.20481 (8)0.0468 (5)
H31A0.52100.74780.23840.070*
H31B0.44680.76650.18390.070*
H31C0.58620.70820.18760.070*
C320.3341 (2)0.61978 (10)0.16417 (6)0.0393 (4)
H32A0.26540.57780.17360.059*
H32B0.42080.59850.14570.059*
H32C0.28120.65670.14210.059*
C1210.79998 (19)0.52058 (9)0.44916 (6)0.0308 (3)
H12A0.89580.49580.43880.037*
H12B0.71590.48730.43760.037*
C1220.7952 (2)0.52887 (12)0.50611 (7)0.0405 (4)
H1220.80140.48240.52540.049*
C1230.7834 (2)0.59327 (14)0.53252 (7)0.0473 (5)
H12C0.77690.64140.51520.057*
H12D0.78150.59160.56890.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01456 (15)0.02122 (16)0.02785 (18)0.00167 (11)0.00244 (12)0.00119 (12)
S20.01566 (15)0.02088 (16)0.02673 (17)0.00277 (11)0.00248 (12)0.00672 (12)
O30.0437 (7)0.0449 (6)0.0230 (5)0.0051 (5)0.0041 (5)0.0008 (5)
O120.0219 (5)0.0229 (4)0.0189 (5)0.0005 (4)0.0003 (4)0.0005 (3)
O220.0358 (6)0.0267 (5)0.0179 (5)0.0019 (4)0.0026 (4)0.0026 (4)
O1510.0369 (7)0.0695 (9)0.0247 (6)0.0058 (6)0.0054 (5)0.0089 (5)
O1520.0418 (7)0.0395 (6)0.0275 (6)0.0092 (5)0.0130 (5)0.0089 (5)
O2510.0747 (10)0.0446 (7)0.0274 (6)0.0040 (7)0.0125 (6)0.0093 (5)
O2520.1446 (18)0.0467 (8)0.0229 (6)0.0033 (10)0.0126 (8)0.0103 (6)
N150.0327 (7)0.0255 (6)0.0223 (6)0.0032 (5)0.0020 (5)0.0039 (4)
N250.0491 (9)0.0390 (7)0.0207 (6)0.0040 (6)0.0080 (6)0.0010 (5)
C30.0333 (8)0.0249 (7)0.0258 (7)0.0027 (6)0.0060 (6)0.0003 (5)
C110.0160 (6)0.0168 (5)0.0245 (7)0.0005 (4)0.0015 (5)0.0009 (5)
C120.0179 (6)0.0157 (5)0.0200 (6)0.0013 (4)0.0001 (5)0.0018 (4)
C130.0154 (6)0.0171 (6)0.0234 (6)0.0011 (4)0.0011 (5)0.0027 (5)
C140.0191 (6)0.0205 (6)0.0238 (7)0.0020 (5)0.0025 (5)0.0034 (5)
C150.0247 (7)0.0194 (6)0.0199 (6)0.0027 (5)0.0024 (5)0.0023 (5)
C160.0192 (6)0.0197 (6)0.0249 (7)0.0017 (5)0.0038 (5)0.0007 (5)
C210.0128 (5)0.0211 (6)0.0230 (6)0.0009 (4)0.0018 (5)0.0042 (5)
C220.0128 (5)0.0243 (6)0.0194 (6)0.0017 (5)0.0002 (4)0.0018 (5)
C230.0133 (5)0.0202 (6)0.0232 (6)0.0009 (4)0.0012 (5)0.0010 (5)
C240.0191 (6)0.0244 (6)0.0232 (7)0.0002 (5)0.0030 (5)0.0053 (5)
C250.0238 (7)0.0293 (7)0.0184 (6)0.0006 (5)0.0043 (5)0.0013 (5)
C260.0176 (6)0.0232 (6)0.0232 (7)0.0000 (5)0.0026 (5)0.0006 (5)
C310.0644 (13)0.0389 (9)0.0372 (9)0.0186 (9)0.0048 (9)0.0014 (7)
C320.0550 (11)0.0372 (8)0.0257 (8)0.0133 (8)0.0079 (7)0.0006 (6)
C1210.0354 (8)0.0277 (7)0.0293 (8)0.0007 (6)0.0022 (6)0.0088 (6)
C1220.0360 (9)0.0578 (11)0.0278 (8)0.0014 (8)0.0024 (7)0.0165 (8)
C1230.0382 (10)0.0802 (14)0.0235 (8)0.0005 (9)0.0004 (7)0.0018 (8)
Geometric parameters (Å, º) top
S1—C23i1.7800 (14)C21—C261.3899 (19)
S1—C111.7824 (13)C21—C221.4171 (18)
C11—C161.3943 (19)C22—O221.3374 (16)
C11—C121.4106 (18)C22—C231.4191 (18)
C12—O121.3694 (16)C23—C241.3878 (19)
C12—C131.4124 (18)C23—S1i1.7800 (14)
C13—C141.3942 (19)C24—C251.393 (2)
C13—S21.7877 (13)C24—H240.9500
C14—C151.3900 (19)C25—C261.3915 (19)
C14—H140.9500C25—N251.4638 (19)
C15—C161.3915 (19)C26—H260.9500
C15—N151.4768 (18)N25—O2511.2277 (19)
C16—H160.9500N25—O2521.2281 (19)
N15—O1521.2300 (17)O22—H220.87 (2)
N15—O1511.2340 (18)O3—C31.220 (2)
O12—C1211.4531 (17)C3—C321.499 (2)
C121—C1221.493 (2)C3—C311.502 (2)
C121—H12A0.9900C31—H31A0.9800
C121—H12B0.9900C31—H31B0.9800
C122—C1231.315 (3)C31—H31C0.9800
C122—H1220.9500C32—H32A0.9800
C123—H12C0.9500C32—H32B0.9800
C123—H12D0.9500C32—H32C0.9800
S2—C211.7824 (13)
C23i—S1—C11101.75 (6)C26—C21—S2118.78 (10)
C16—C11—C12120.56 (12)C22—C21—S2120.86 (10)
C16—C11—S1118.74 (10)O22—C22—C21123.61 (12)
C12—C11—S1120.62 (10)O22—C22—C23117.29 (12)
O12—C12—C11119.76 (11)C21—C22—C23119.09 (12)
O12—C12—C13120.48 (11)C24—C23—C22120.23 (12)
C11—C12—C13119.76 (12)C24—C23—S1i119.04 (10)
C14—C13—C12119.63 (12)C22—C23—S1i120.38 (10)
C14—C13—S2117.94 (10)C23—C24—C25119.09 (12)
C12—C13—S2122.29 (10)C23—C24—H24120.5
C15—C14—C13119.00 (12)C25—C24—H24120.5
C15—C14—H14120.5C26—C25—C24122.09 (13)
C13—C14—H14120.5C26—C25—N25118.68 (13)
C14—C15—C16122.85 (13)C24—C25—N25119.23 (13)
C14—C15—N15118.19 (12)C21—C26—C25119.08 (13)
C16—C15—N15118.89 (12)C21—C26—H26120.5
C15—C16—C11118.08 (12)C25—C26—H26120.5
C15—C16—H16121.0O251—N25—O252123.24 (15)
C11—C16—H16121.0O251—N25—C25118.97 (14)
O152—N15—O151124.14 (13)O252—N25—C25117.79 (14)
O152—N15—C15117.62 (12)C22—O22—H22117.1 (15)
O151—N15—C15118.24 (12)O3—C3—C32120.91 (15)
C12—O12—C121112.10 (10)O3—C3—C31121.85 (15)
O12—C121—C122109.84 (13)C32—C3—C31117.22 (14)
O12—C121—H12A109.7C3—C31—H31A109.5
C122—C121—H12A109.7C3—C31—H31B109.5
O12—C121—H12B109.7H31A—C31—H31B109.5
C122—C121—H12B109.7C3—C31—H31C109.5
H12A—C121—H12B108.2H31A—C31—H31C109.5
C123—C122—C121127.24 (17)H31B—C31—H31C109.5
C123—C122—H122116.4C3—C32—H32A109.5
C121—C122—H122116.4C3—C32—H32B109.5
C122—C123—H12C120.0H32A—C32—H32B109.5
C122—C123—H12D120.0C3—C32—H32C109.5
H12C—C123—H12D120.0H32A—C32—H32C109.5
C21—S2—C13101.06 (6)H32B—C32—H32C109.5
C26—C21—C22120.21 (12)
C23i—S1—C11—C16118.89 (11)O12—C121—C122—C1230.6 (2)
C23i—S1—C11—C1264.61 (11)C14—C13—S2—C21127.05 (10)
C16—C11—C12—O12177.96 (11)C12—C13—S2—C2157.23 (11)
S1—C11—C12—O121.53 (16)C13—S2—C21—C26114.33 (11)
C16—C11—C12—C133.12 (18)C13—S2—C21—C2270.09 (11)
S1—C11—C12—C13179.55 (9)C26—C21—C22—O22176.19 (12)
O12—C12—C13—C14177.32 (11)S2—C21—C22—O220.67 (18)
C11—C12—C13—C143.76 (18)C26—C21—C22—C234.90 (18)
O12—C12—C13—S21.67 (16)S2—C21—C22—C23179.58 (9)
C11—C12—C13—S2179.41 (9)O22—C22—C23—C24178.10 (12)
C12—C13—C14—C151.49 (18)C21—C22—C23—C242.93 (18)
S2—C13—C14—C15177.32 (10)O22—C22—C23—S1i4.98 (16)
C13—C14—C15—C161.5 (2)C21—C22—C23—S1i176.05 (9)
C13—C14—C15—N15178.57 (11)C22—C23—C24—C251.16 (19)
C14—C15—C16—C112.2 (2)S1i—C23—C24—C25172.05 (10)
N15—C15—C16—C11179.21 (11)C23—C24—C25—C263.4 (2)
C12—C11—C16—C150.18 (19)C23—C24—C25—N25177.02 (13)
S1—C11—C16—C15176.68 (10)C22—C21—C26—C252.74 (19)
C14—C15—N15—O152177.42 (13)S2—C21—C26—C25178.35 (10)
C16—C15—N15—O1520.27 (18)C24—C25—C26—C211.5 (2)
C14—C15—N15—O1512.63 (19)N25—C25—C26—C21178.98 (13)
C16—C15—N15—O151179.79 (13)C26—C25—N25—O2518.0 (2)
C11—C12—O12—C12193.38 (14)C24—C25—N25—O251172.48 (15)
C13—C12—O12—C12187.71 (14)C26—C25—N25—O252172.26 (17)
C12—O12—C121—C122178.16 (12)C24—C25—N25—O2527.3 (2)
Symmetry code: (i) x+3/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O30.87 (2)1.94 (2)2.7558 (16)155 (2)
(3b2) syn-22,42-dihydroxy-15,25,35,45-tetranitro-12,32– bis(prop-2-enoxy)thiacalix[4]arene top
Crystal data top
C30H20N4O12S4F(000) = 1552
Mr = 756.74Dx = 1.568 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 23347 reflections
a = 17.2475 (17) Åθ = 3.4–25.8°
b = 20.4150 (19) ŵ = 0.37 mm1
c = 9.102 (1) ÅT = 173 K
V = 3204.9 (6) Å3Plate, colourless
Z = 40.39 × 0.12 × 0.04 mm
Data collection top
STOE IPDS-II two-circle-
diffractometer
3127 independent reflections
Radiation source: fine-focus sealed tube2375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
ω scansθmax = 25.8°, θmin = 3.4°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2021
Tmin = 0.892, Tmax = 0.961k = 2224
44126 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.257 w = 1/[σ2(Fo2) + (0.1315P)2 + 3.5315P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3127 reflectionsΔρmax = 0.74 e Å3
239 parametersΔρmin = 0.48 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (19)
Crystal data top
C30H20N4O12S4V = 3204.9 (6) Å3
Mr = 756.74Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 17.2475 (17) ŵ = 0.37 mm1
b = 20.4150 (19) ÅT = 173 K
c = 9.102 (1) Å0.39 × 0.12 × 0.04 mm
Data collection top
STOE IPDS-II two-circle-
diffractometer
3127 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
2375 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.961Rint = 0.098
44126 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0931 restraint
wR(F2) = 0.257H-atom parameters constrained
S = 1.10Δρmax = 0.74 e Å3
3127 reflectionsΔρmin = 0.48 e Å3
239 parameters
Special details top

Experimental.

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.61872 (9)0.61341 (8)0.82180 (14)0.0656 (5)
S20.69118 (9)0.61361 (8)0.22341 (16)0.0693 (5)
O120.72499 (18)0.62180 (17)0.5518 (4)0.0529 (9)
O220.6226 (3)0.75000.2025 (6)0.089 (2)
H220.60690.78880.19480.133*0.50
O250.9692 (3)0.6984 (3)0.3656 (11)0.145 (3)
O1510.3995 (2)0.5491 (2)0.2899 (4)0.0697 (11)
O1520.3698 (2)0.5563 (2)0.5220 (5)0.0772 (13)
O320.5521 (3)0.75000.7811 (7)0.090 (2)
H320.53620.78880.77410.134*0.50
O350.8993 (3)0.7006 (3)0.9325 (11)0.157 (4)
N150.4162 (2)0.5614 (2)0.4195 (5)0.0540 (10)
N250.9362 (4)0.75000.3509 (11)0.082 (2)
N350.8678 (4)0.75000.9116 (8)0.0654 (18)
C110.5931 (3)0.6069 (2)0.6329 (5)0.0491 (11)
C120.6480 (2)0.6114 (2)0.5186 (5)0.0438 (10)
C130.6245 (3)0.6070 (2)0.3721 (5)0.0489 (11)
C140.5475 (3)0.5910 (2)0.3386 (5)0.0506 (11)
H140.53100.58680.23950.061*
C150.4963 (2)0.5814 (2)0.4531 (5)0.0470 (11)
C160.5166 (3)0.5907 (3)0.5992 (5)0.0508 (11)
H160.47910.58600.67490.061*
C210.7377 (3)0.6903 (3)0.2582 (5)0.0575 (13)
C220.6982 (4)0.75000.2389 (7)0.0552 (17)
C250.8531 (4)0.75000.3108 (9)0.062 (2)
C260.8163 (3)0.6903 (3)0.2952 (7)0.0628 (14)
H260.84380.65040.30910.075*
C310.6675 (3)0.6902 (3)0.8310 (5)0.0510 (12)
C320.6282 (4)0.75000.8138 (7)0.0545 (18)
C350.7837 (4)0.75000.8833 (7)0.0501 (16)
C360.7464 (3)0.6904 (3)0.8664 (5)0.0497 (11)
H360.77390.65050.87860.060*
C1210.7672 (3)0.5614 (3)0.5776 (8)0.0747 (17)
H12A0.76160.53170.49220.090*
H12B0.74650.53890.66560.090*
C1220.8506 (3)0.5785 (3)0.6001 (7)0.0703 (16)
H12G0.86300.61680.65430.084*0.726 (15)
H12H0.88440.54260.61810.084*0.274 (15)
C1230.9054 (5)0.5438 (4)0.5499 (9)0.069 (3)*0.726 (15)
H12C0.95330.56370.52390.083*0.726 (15)
H12D0.89860.49790.53810.083*0.726 (15)
C1240.8827 (11)0.6354 (7)0.598 (2)0.058 (6)*0.274 (15)
H12E0.93440.64020.56420.070*0.274 (15)
H12F0.85460.67270.63110.070*0.274 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0660 (8)0.0898 (11)0.0411 (7)0.0310 (7)0.0067 (5)0.0057 (6)
S20.0691 (9)0.0859 (11)0.0528 (8)0.0209 (7)0.0181 (6)0.0188 (7)
O120.0364 (16)0.062 (2)0.060 (2)0.0051 (14)0.0038 (14)0.0023 (15)
O220.045 (3)0.169 (7)0.052 (3)0.0000.006 (2)0.000
O250.050 (3)0.080 (3)0.305 (10)0.010 (2)0.012 (4)0.008 (5)
O320.034 (3)0.160 (7)0.075 (4)0.0000.007 (2)0.000
O350.059 (3)0.064 (3)0.347 (12)0.010 (2)0.065 (5)0.014 (5)
O1510.057 (2)0.084 (3)0.068 (2)0.010 (2)0.0290 (18)0.007 (2)
O1520.0428 (19)0.093 (3)0.096 (3)0.0105 (19)0.007 (2)0.021 (2)
N150.041 (2)0.055 (2)0.066 (3)0.0013 (18)0.0107 (19)0.0011 (19)
N250.040 (3)0.067 (5)0.139 (7)0.0000.010 (4)0.000
N350.049 (3)0.050 (4)0.098 (5)0.0000.019 (3)0.000
C110.045 (2)0.054 (3)0.049 (2)0.004 (2)0.005 (2)0.004 (2)
C120.035 (2)0.046 (2)0.050 (2)0.0041 (17)0.0049 (18)0.0015 (19)
C130.044 (2)0.054 (3)0.049 (2)0.005 (2)0.0015 (19)0.005 (2)
C140.052 (3)0.054 (3)0.045 (2)0.003 (2)0.009 (2)0.001 (2)
C150.036 (2)0.053 (3)0.053 (3)0.0039 (19)0.0097 (18)0.000 (2)
C160.040 (2)0.057 (3)0.055 (3)0.002 (2)0.0004 (19)0.002 (2)
C210.051 (3)0.076 (4)0.046 (3)0.009 (2)0.016 (2)0.007 (2)
C220.052 (4)0.077 (5)0.037 (3)0.0000.011 (3)0.000
C250.041 (4)0.064 (5)0.081 (5)0.0000.018 (3)0.000
C260.048 (3)0.066 (3)0.074 (4)0.002 (2)0.021 (2)0.007 (3)
C310.048 (2)0.076 (3)0.029 (2)0.010 (2)0.0011 (18)0.002 (2)
C320.039 (3)0.088 (5)0.036 (3)0.0000.001 (3)0.000
C350.039 (3)0.063 (4)0.048 (4)0.0000.010 (3)0.000
C360.050 (3)0.064 (3)0.035 (2)0.002 (2)0.0040 (18)0.002 (2)
C1210.045 (3)0.068 (4)0.110 (5)0.002 (3)0.021 (3)0.005 (3)
C1220.047 (3)0.089 (4)0.075 (4)0.007 (3)0.015 (3)0.013 (3)
Geometric parameters (Å, º) top
S1—C311.780 (5)C123—H12D0.9500
S1—C111.780 (5)C124—H12E0.9500
C11—C161.394 (6)C124—H12F0.9500
C11—C121.410 (7)N15—O1521.233 (6)
C12—O121.378 (5)N15—O1511.239 (5)
C12—C131.397 (7)S2—C211.787 (6)
C13—C141.402 (7)C21—C261.397 (8)
C13—S21.781 (5)C21—C221.408 (7)
C14—C151.380 (7)C22—O221.346 (9)
C14—H140.9500C25—C261.381 (7)
C15—C161.389 (7)C25—N251.480 (10)
C15—N151.473 (6)C26—H260.9500
C16—H160.9500O22—H220.8399
O12—C1211.451 (7)N25—O251.204 (6)
C121—C1221.494 (8)C31—C361.399 (7)
C121—H12A0.9900C31—C321.405 (6)
C121—H12B0.9900C32—O321.347 (8)
C122—C1231.266 (9)C35—C361.385 (6)
C122—C1241.288 (12)C35—N351.473 (8)
C122—H12G0.9500C36—H360.9500
C122—H12H0.9500O32—H320.8400
C123—H12C0.9500N35—O351.162 (6)
C31—S1—C11103.2 (2)C122—C124—H12F120.0
C16—C11—C12119.3 (4)H12E—C124—H12F120.0
C16—C11—S1117.7 (4)O152—N15—O151123.6 (4)
C12—C11—S1122.7 (3)O152—N15—C15118.3 (4)
O12—C12—C13119.9 (4)O151—N15—C15118.1 (4)
O12—C12—C11119.7 (4)C13—S2—C21102.8 (2)
C13—C12—C11120.3 (4)C26—C21—C22119.9 (5)
C12—C13—C14119.8 (4)C26—C21—S2118.6 (5)
C12—C13—S2122.2 (3)C22—C21—S2121.3 (4)
C14—C13—S2117.7 (4)O22—C22—C21i120.0 (3)
C15—C14—C13118.4 (4)O22—C22—C21120.0 (3)
C15—C14—H14120.8C21i—C22—C21120.0 (7)
C13—C14—H14120.8C26i—C25—C26123.9 (7)
C14—C15—C16122.8 (4)C26i—C25—N25118.0 (4)
C14—C15—N15118.9 (4)C26—C25—N25118.0 (4)
C16—C15—N15118.3 (4)C25—C26—C21118.1 (6)
C15—C16—C11118.8 (4)C25—C26—H26121.0
C15—C16—H16120.6C21—C26—H26121.0
C11—C16—H16120.6C22—O22—H22109.5
C12—O12—C121112.8 (4)O25—N25—O25i122.0 (8)
O12—C121—C122107.9 (5)O25—N25—C25119.0 (4)
O12—C121—H12A110.1O25i—N25—C25119.0 (4)
C122—C121—H12A110.1C36—C31—C32119.4 (5)
O12—C121—H12B110.1C36—C31—S1118.3 (4)
C122—C121—H12B110.1C32—C31—S1122.2 (4)
H12A—C121—H12B108.4O32—C32—C31119.6 (3)
C123—C122—C124100.3 (11)O32—C32—C31i119.6 (3)
C123—C122—C121122.6 (7)C31—C32—C31i120.7 (6)
C124—C122—C121128.5 (10)C36i—C35—C36122.9 (6)
C123—C122—H12G118.7C36i—C35—N35118.5 (3)
C121—C122—H12G118.7C36—C35—N35118.5 (3)
C124—C122—H12H115.8C35—C36—C31118.8 (5)
C121—C122—H12H115.8C35—C36—H36120.6
H12G—C122—H12H114.1C31—C36—H36120.6
C122—C123—H12C120.0C32—O32—H32109.5
C122—C123—H12D120.0O35—N35—O35i120.7 (7)
H12C—C123—H12D120.0O35—N35—C35119.3 (4)
C122—C124—H12E120.0O35i—N35—C35119.2 (4)
C31—S1—C11—C16130.5 (4)C13—S2—C21—C26113.3 (4)
C31—S1—C11—C1255.5 (5)C13—S2—C21—C2271.3 (5)
C16—C11—C12—O12174.4 (4)C26—C21—C22—O22179.6 (5)
S1—C11—C12—O120.5 (6)S2—C21—C22—O224.3 (8)
C16—C11—C12—C137.2 (7)C26—C21—C22—C21i0.7 (9)
S1—C11—C12—C13178.9 (4)S2—C21—C22—C21i176.0 (3)
O12—C12—C13—C14174.6 (4)C26i—C25—C26—C211.4 (12)
C11—C12—C13—C147.0 (7)N25—C25—C26—C21179.6 (6)
O12—C12—C13—S20.7 (7)C22—C21—C26—C250.3 (8)
C11—C12—C13—S2179.1 (4)S2—C21—C26—C25175.1 (5)
C12—C13—C14—C151.6 (7)C26i—C25—N25—O25179.7 (9)
S2—C13—C14—C15175.8 (4)C26—C25—N25—O251.4 (13)
C13—C14—C15—C163.7 (8)C26i—C25—N25—O25i1.4 (13)
C13—C14—C15—N15177.0 (4)C26—C25—N25—O25i179.7 (9)
C14—C15—C16—C113.5 (8)C11—S1—C31—C36114.5 (4)
N15—C15—C16—C11177.2 (4)C11—S1—C31—C3269.9 (5)
C12—C11—C16—C152.0 (7)C36—C31—C32—O32179.4 (5)
S1—C11—C16—C15176.2 (4)S1—C31—C32—O323.8 (8)
C13—C12—O12—C12193.8 (6)C36—C31—C32—C31i0.4 (9)
C11—C12—O12—C12187.9 (6)S1—C31—C32—C31i175.9 (3)
C12—O12—C121—C122175.4 (5)C36i—C35—C36—C310.1 (9)
O12—C121—C122—C123141.3 (7)N35—C35—C36—C31176.3 (5)
O12—C121—C122—C1240.0 (14)C32—C31—C36—C350.1 (7)
C14—C15—N15—O152176.3 (5)S1—C31—C36—C35175.8 (4)
C16—C15—N15—O1523.0 (7)C36i—C35—N35—O35176.6 (8)
C14—C15—N15—O1515.2 (7)C36—C35—N35—O357.1 (12)
C16—C15—N15—O151175.5 (5)C36i—C35—N35—O35i7.1 (12)
C12—C13—S2—C2155.0 (5)C36—C35—N35—O35i176.6 (8)
C14—C13—S2—C21131.0 (4)
Symmetry code: (i) x, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O25ii0.842.452.915 (8)116
O22—H22···S2i0.842.483.031 (3)124
O32—H32···S1i0.842.493.039 (3)124
Symmetry codes: (i) x, y+3/2, z; (ii) x1/2, y+3/2, z+1/2.

Experimental details

(3a)(3b1)(3b2)
Crystal data
Chemical formulaC30H24O4S4C30H20N4O12S4·2C3H6OC30H20N4O12S4
Mr576.73872.90756.74
Crystal system, space groupMonoclinic, P21/cOrthorhombic, PccnOrthorhombic, Pnma
Temperature (K)173173173
a, b, c (Å)9.2591 (8), 18.5282 (13), 16.7729 (17)8.8760 (3), 17.3100 (5), 26.0798 (10)17.2475 (17), 20.4150 (19), 9.102 (1)
α, β, γ (°)90, 104.297 (7), 9090, 90, 9090, 90, 90
V3)2788.3 (4)4007.0 (2)3204.9 (6)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.380.310.37
Crystal size (mm)0.36 × 0.12 × 0.100.42 × 0.37 × 0.190.39 × 0.12 × 0.04
Data collection
DiffractometerSTOE IPDS-II two-circle-
diffractometer
STOE IPDS-II two-circle-
diffractometer
STOE IPDS-II two-circle-
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
Multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.877, 0.9630.881, 0.9440.892, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
39745, 6073, 4194 56923, 4617, 4227 44126, 3127, 2375
Rint0.0960.0670.098
(sin θ/λ)max1)0.6410.6530.612
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.124, 1.00 0.034, 0.084, 1.06 0.093, 0.257, 1.10
No. of reflections607346173127
No. of parameters361267239
No. of restraints001
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.330.31, 0.200.74, 0.48

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.

Hydrogen-bond geometry (Å, º) for (3a) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O320.83 (3)2.17 (3)2.904 (2)146 (3)
O42—H42···O320.82 (3)2.23 (3)2.939 (2)146 (3)
Hydrogen-bond geometry (Å, º) for (3b1) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O30.87 (2)1.94 (2)2.7558 (16)155 (2)
Hydrogen-bond geometry (Å, º) for (3b2) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O25i0.842.452.915 (8)116
O22—H22···S2ii0.842.483.031 (3)124
O32—H32···S1ii0.842.493.039 (3)124
Symmetry codes: (i) x1/2, y+3/2, z+1/2; (ii) x, y+3/2, z.
Dihedral angles (°) between the reference plane defined by the four S atoms and the mean planes through the aromatic rings for the three structures top
p1p1p3p4
3a71.24 (5)146.22 (5)102.27 (5)147.31 (5)
3b195.34 (3)89.24 (3)
3b2103.09 (11)89.10 (17)89.64 (15)
p1: plane through C11–C16; p2: plane through C21–C26; p3: plane through C41 and C32–C36; p4: plane through C41–C46. In (3b2) C23 and C24 are symmetry equivalents of C21 and C26, and C33 and C34 are symmetry equivalents of C31 and C36.
MMFF94 calculated energies (in kcal mol−1) of the cone and 1,3-alternate conformers of (III) and (IV) (roman numbers are used to characterize the calculations) top
IIIaIIIbIIIcIVaIVbIVc
coaltcoaltcoaltcoaltcoaltcoalt
bond54.650.070.667.977.574.045.049.062.462.669.274.4
n-bond98.399.3146.2141.4143.4145.779.586.1187.3192.4126.4128.9
total152.9149.3216.8209.3220.9219.7124.5135.1249.7255.0195.6203.3
ΔE3.67.51.2-10.6-5.3-7.7
The descriptors a, b and c refer to p-substituents H, NO2, and tBu. co: cone conformation; alt: 1,3-alternate conformation; bond: sum of bonding interactions; n-bond: sum of non-bonding interactions; total: sum of all the energy contributions; ΔE: total(cone) - total(alt)
 

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