Download citation
Download citation
link to html
The acyclic tetraphenolic derivative 2,2'-methyl­ene­bis[6-(3-tert-butyl-2-hydroxy-5-methyl­benzyl)-4-methyl­phenol] reacts with excess triethyl­amine in aceto­nitrile to form a molecular complex, i.e. triethyl­ammonium 2-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-6-[3-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-2-hydroxy-5-methylbenzyl]-4-methylphenolate aceto­nitrile sol­vate, C6H16N+·­C39H47O4-·­C2H3N, where the organic HNEt3+ cation is included in the partial cone defined by the aromatic faces of the acyclic poly­phenolate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006582/gs1087sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006582/gs1087Isup2.hkl
Contains datablock I

CCDC reference: 150343

Comment top

The separation of radioactive metal cations from waste solutions produced by the nuclear industry is an important goal for the environmental management and recycling of nuclear fuels. In this respect, the comparative study of various classes of complexing agents has been undertaken, in particular the calixarene and their acyclic counterparts. The latter are very flexible ligands which have the potential to fit the coordination requirements of actinide cations (Thuéry & Nierlich, 1997). Full characterization of the organic extractants including determination of their conformation in the solid state is important for the understanding of extraction processes. If there are now numerous examples of crystal structures of calix[4]arenes reported in the literature, those of their acyclic homologues are less common (Casiraghi et al., 1982; Paulus & Böhmer, 1984; Usui et al., 1991). All these reports concern the fully protonated ligands. Herein we present the crystal structure of the triethylammonium salt of [methylenebis-2,2'-(6,6'- (3-tert-butyl-2-hydroxy-5-methyl)benzyl-4,4'-methyl)phenol].(acetonitrile), (I), the first of an anionic derivative of an acyclic tetraphenol. \sch

The crystal structure of (I) (Fig. 1) reveals that the tetraphenolic derivative has been deprotonated once by reaction with excess triethylamine and that the anion formed is stabilized by strong intramolecular hydrogen bonds. The triethylammonium cation donates an hydrogen bond to the deprotonated phenolate group O3. Two other hydrogen bonds are donated to O3 by O2 and O4, while O2 receives one from O1. This arrangement is reminiscent of the hydrogen-bond pattern classically stabilizing the deprotonated calix[4]arene (Gutsche, 1998).

The conformation of (I) in the solid state can be described as syn-anti (Casiraghi et al., 1982; Perrin & Oehler, 1990). Consequently, three of its aromatic faces are organized into a partial cone. This cavity is occupied by one of the terminal methyl group of a triethylammonium cation hydrogen bound to an adjacent phenolate (Fig. 2). This methyl group is positioned 1.17 (2) Å below the plane defined by the lips of the partial cone (C28, C38 and C48) that can be considered as the limit of the cavity. Interestingly, the inclusion of cations in the aromatic cavity of calix[4]arenes is a well known feature of this class of macrocycles (Leverd et al., 2000). Conversely, the formation of host–guest complexes of acyclic oligomers (induced-fit inclusion) has only been evidenced for neutral organic molecules (Sone et al., 1989; Usui et al., 1991) and not for charged species. Compound (I) is, to the best of our knowledge, the first example of such an inclusion occurring with a cation.

The extended structure (Fig. 2) consists of residues organizing the solid into rods parallel to the [010] direction. In contrast to previously reported structures of polyphenolic oligomers which pack into hydrogen bound dimers or infinite chains, the arrangement of the solid in (I) results from the interactions due to both hydrogen bonds and inclusion phenomena.

Experimental top

The tetraphenol was synthesized according to the published method (Weber et al., 1999). Single crystals of the title compound suitable for structure determination were obtained by slow evaporation (298 K) of an acetonitrile solution containing a mixture of the tetraphenol and a twofold excess of triethylamine.

Refinement top

Hydrogen atoms of the ligand were included as riding atoms at calculated positions (U = 1.2 times that of corresponding carbon) with the exception of those involved in hydrogen bonding which were positioned from the Fourier difference map and refined.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: DENZO; data reduction: DENZO; 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.

Figures top
[Figure 1] Fig. 1. Drawing of the title compound with atom labelling. Displacement ellipsoids are drawn at the 20% probability level except for the H atoms which are represented as spheres of arbitrary radii. H atoms which do not participate in hydrogen bonding have been omitted for clarity. Hydrogen bonds are indicated by dashed lines.
[Figure 2] Fig. 2. View of the extended structure.
(I) top
Crystal data top
C6H16N+·C39H47O4·C2H3NF(000) = 1576
Mr = 723.02Dx = 1.141 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 16.024 (3) ÅCell parameters from all reflections
b = 17.073 (3) Åθ = 2.7–26.4°
c = 16.067 (3) ŵ = 0.07 mm1
β = 106.75 (3)°T = 100 K
V = 4209.1 (15) Å3Block, colourless
Z = 40.2 × 0.2 × 0.15 mm
Data collection top
Nonius CCD
diffractometer
5631 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 26.4°, θmin = 2.7°
ω–scansh = 019
15352 measured reflectionsk = 2121
8472 independent reflectionsl = 2018
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0501P)2 + 0.8636P]
where P = (Fo2 + 2Fc2)/3
8472 reflections(Δ/σ)max < 0.001
508 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C6H16N+·C39H47O4·C2H3NV = 4209.1 (15) Å3
Mr = 723.02Z = 4
Monoclinic, P21/nMo Kα radiation
a = 16.024 (3) ŵ = 0.07 mm1
b = 17.073 (3) ÅT = 100 K
c = 16.067 (3) Å0.2 × 0.2 × 0.15 mm
β = 106.75 (3)°
Data collection top
Nonius CCD
diffractometer
5631 reflections with I > 2σ(I)
15352 measured reflectionsRint = 0.046
8472 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.19 e Å3
8472 reflectionsΔρmin = 0.19 e Å3
508 parameters
Special details top

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. Hydrogen atoms of the ligand were included as riding atoms at calculated positions (U=1.2 times that of corresponding carbon) with the exception of those involved in hydrogen bonding which were positionned from the molecules were introduced Fourier difference map and refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.32625 (10)0.12633 (7)0.55719 (8)0.0313 (3)
O20.28551 (8)0.20731 (7)0.40769 (8)0.0257 (3)
O30.28826 (8)0.19770 (6)0.25329 (7)0.0211 (3)
O40.43541 (9)0.28074 (7)0.29659 (8)0.0275 (3)
C110.32510 (12)0.16343 (10)0.63245 (11)0.0222 (4)
C120.32054 (11)0.11636 (10)0.70262 (11)0.0223 (4)
C130.32214 (13)0.15443 (11)0.77964 (12)0.0285 (4)
H13A0.31960.12430.82710.034*
C140.32738 (14)0.23598 (11)0.78903 (12)0.0323 (5)
C150.33020 (13)0.27982 (11)0.71751 (12)0.0303 (4)
H15A0.33360.33410.72250.036*
C160.32821 (12)0.24578 (10)0.63875 (11)0.0231 (4)
C170.32661 (12)0.29687 (10)0.56090 (11)0.0249 (4)
H17A0.34390.34970.58090.030*
H17B0.36900.27700.53350.030*
C180.33149 (19)0.27309 (14)0.87532 (14)0.0539 (7)
H18A0.36090.23850.92150.081*
H18B0.27340.28270.87840.081*
H18C0.36270.32170.88090.081*
C190.31458 (13)0.02651 (11)0.69526 (12)0.0285 (4)
C19A0.30778 (15)0.01189 (12)0.77920 (13)0.0383 (5)
H19A0.25620.00640.79200.057*
H19B0.35810.00150.82620.057*
H19C0.30480.06770.77200.057*
C19B0.39693 (16)0.00555 (12)0.67726 (15)0.0432 (6)
H19D0.40100.01450.62270.065*
H19E0.39420.06170.67480.065*
H19F0.44720.01040.72290.065*
C19C0.23348 (16)0.00258 (13)0.62246 (15)0.0494 (6)
H19G0.18220.01940.63680.074*
H19H0.23240.05330.61600.074*
H19I0.23510.02670.56900.074*
C210.21966 (12)0.25387 (10)0.41832 (11)0.0219 (4)
C220.23800 (12)0.29970 (10)0.49399 (11)0.0226 (4)
C230.17275 (13)0.34865 (10)0.50564 (12)0.0258 (4)
H23A0.18430.37970.55520.031*
C240.09038 (13)0.35234 (11)0.44490 (12)0.0282 (4)
C250.07421 (13)0.30441 (10)0.37202 (12)0.0264 (4)
H25A0.01940.30580.33150.032*
C260.13730 (12)0.25436 (10)0.35764 (11)0.0212 (4)
C270.11637 (12)0.20294 (10)0.27688 (11)0.0245 (4)
H27A0.14810.15410.29130.029*
H27B0.05470.19070.25990.029*
C280.02158 (14)0.40659 (13)0.45894 (14)0.0402 (5)
H28A0.04260.43110.51490.060*
H28B0.03020.37720.45640.060*
H28C0.00850.44610.41450.060*
C310.22443 (12)0.23644 (9)0.19300 (11)0.0199 (4)
C320.13873 (12)0.23980 (10)0.19998 (11)0.0212 (4)
C330.07487 (12)0.27958 (10)0.13676 (11)0.0247 (4)
H33A0.01860.28200.14200.030*
C340.09231 (12)0.31590 (10)0.06603 (12)0.0260 (4)
C350.17751 (12)0.31242 (10)0.06109 (11)0.0242 (4)
H35A0.19060.33660.01450.029*
C360.24386 (12)0.27420 (9)0.12298 (11)0.0207 (4)
C370.33612 (12)0.27597 (10)0.11588 (11)0.0229 (4)
H37A0.33360.27520.05480.027*
H37B0.36590.22870.14220.027*
C380.02127 (13)0.35581 (12)0.00416 (13)0.0361 (5)
H38A0.01720.38320.02190.054*
H38B0.01110.31720.04400.054*
H38C0.04700.39240.03490.054*
C410.43774 (12)0.34478 (10)0.24627 (11)0.0225 (4)
C420.38952 (11)0.34635 (10)0.15836 (11)0.0220 (4)
C430.39326 (12)0.41272 (10)0.10948 (12)0.0251 (4)
H43A0.36070.41390.05130.030*
C440.44384 (13)0.47724 (10)0.14446 (12)0.0276 (4)
C450.49240 (12)0.47294 (10)0.23148 (12)0.0266 (4)
H45A0.52710.51550.25570.032*
C460.49189 (12)0.40814 (11)0.28446 (12)0.0247 (4)
C470.55121 (13)0.40428 (12)0.37861 (12)0.0304 (4)
C47A0.49863 (15)0.38958 (13)0.44372 (13)0.0397 (5)
H47A0.53770.38650.50150.060*
H47B0.46710.34120.42960.060*
H47C0.45830.43180.44060.060*
C47B0.60091 (15)0.48141 (13)0.40571 (14)0.0411 (5)
H47D0.63520.47810.46540.062*
H47E0.56010.52380.39890.062*
H47F0.63850.49060.36970.062*
C47C0.61828 (14)0.33849 (13)0.38518 (14)0.0399 (5)
H47G0.65490.33470.44400.060*
H47H0.65340.35000.34740.060*
H47I0.58840.28970.36830.060*
C480.44711 (15)0.54927 (12)0.09064 (14)0.0386 (5)
H48A0.49530.58160.12090.058*
H48B0.39380.57820.08110.058*
H48C0.45430.53370.03570.058*
N10.18773 (10)0.54503 (9)0.26795 (10)0.0233 (3)
C10.27162 (12)0.50116 (10)0.30186 (12)0.0263 (4)
H1AA0.30430.52370.35710.032*
H1AB0.30600.50750.26160.032*
C20.25848 (14)0.41482 (11)0.31432 (14)0.0335 (5)
H2A10.31410.38990.33690.050*
H2A20.22810.39170.25950.050*
H2A30.22480.40810.35450.050*
C30.13098 (13)0.54373 (11)0.32795 (12)0.0279 (4)
H1BA0.10730.49150.32790.033*
H1BB0.08250.57930.30570.033*
C40.17847 (14)0.56660 (12)0.42072 (13)0.0338 (5)
H2B10.21500.52410.44880.051*
H2B20.13680.57810.45160.051*
H2B30.21370.61210.42050.051*
C50.13507 (13)0.51849 (11)0.17922 (12)0.0292 (4)
H1CA0.08630.55400.15790.035*
H1CB0.11160.46690.18410.035*
C60.18634 (15)0.51513 (11)0.11391 (13)0.0364 (5)
H2C10.14730.50640.05690.055*
H2C20.22770.47310.12860.055*
H2C30.21660.56380.11460.055*
N20.03583 (14)0.32827 (12)0.66329 (16)0.0591 (6)
C70.09630 (15)0.19802 (12)0.62241 (17)0.0457 (6)
H1A0.06370.15500.63580.069*
H1B0.15660.19260.65470.069*
H1C0.09080.19800.56130.069*
C80.06287 (15)0.27073 (13)0.64570 (15)0.0414 (5)
H30.2028 (14)0.5996 (13)0.2598 (14)0.046 (6)*
H10.3161 (19)0.1622 (17)0.5088 (19)0.086 (10)*
H40.3804 (17)0.2501 (14)0.2718 (15)0.058 (7)*
H20.2845 (16)0.2030 (14)0.3426 (17)0.062 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0520 (9)0.0244 (7)0.0188 (7)0.0055 (6)0.0123 (6)0.0007 (6)
O20.0291 (8)0.0289 (7)0.0210 (7)0.0093 (5)0.0102 (6)0.0019 (6)
O30.0247 (7)0.0201 (6)0.0186 (6)0.0032 (5)0.0062 (5)0.0015 (5)
O40.0287 (8)0.0296 (7)0.0224 (7)0.0043 (6)0.0043 (6)0.0053 (6)
C110.0214 (10)0.0260 (9)0.0191 (9)0.0031 (7)0.0056 (7)0.0026 (8)
C120.0181 (9)0.0266 (9)0.0215 (9)0.0028 (7)0.0048 (7)0.0002 (8)
C130.0314 (11)0.0350 (10)0.0198 (9)0.0054 (8)0.0088 (8)0.0050 (8)
C140.0425 (13)0.0341 (10)0.0207 (10)0.0064 (9)0.0097 (9)0.0034 (8)
C150.0376 (12)0.0281 (10)0.0249 (10)0.0015 (8)0.0084 (9)0.0050 (8)
C160.0207 (10)0.0272 (9)0.0216 (9)0.0000 (7)0.0065 (8)0.0009 (8)
C170.0271 (11)0.0236 (9)0.0246 (10)0.0018 (8)0.0086 (8)0.0004 (8)
C180.093 (2)0.0430 (13)0.0291 (12)0.0112 (13)0.0235 (13)0.0037 (10)
C190.0322 (11)0.0260 (10)0.0254 (10)0.0015 (8)0.0052 (8)0.0036 (8)
C19A0.0463 (14)0.0321 (11)0.0396 (12)0.0005 (10)0.0173 (11)0.0092 (10)
C19B0.0614 (16)0.0332 (11)0.0424 (13)0.0181 (11)0.0268 (12)0.0117 (10)
C19C0.0564 (16)0.0328 (11)0.0461 (14)0.0129 (11)0.0055 (12)0.0051 (11)
C210.0265 (10)0.0184 (8)0.0234 (9)0.0046 (7)0.0112 (8)0.0043 (7)
C220.0290 (10)0.0185 (8)0.0220 (9)0.0007 (7)0.0100 (8)0.0033 (7)
C230.0366 (12)0.0210 (9)0.0231 (9)0.0039 (8)0.0138 (9)0.0006 (8)
C240.0326 (11)0.0271 (9)0.0278 (10)0.0074 (8)0.0135 (9)0.0047 (8)
C250.0251 (10)0.0298 (10)0.0253 (10)0.0031 (8)0.0088 (8)0.0040 (8)
C260.0254 (10)0.0207 (8)0.0204 (9)0.0008 (7)0.0110 (8)0.0015 (7)
C270.0237 (10)0.0246 (9)0.0261 (10)0.0026 (8)0.0088 (8)0.0006 (8)
C280.0413 (13)0.0436 (12)0.0383 (12)0.0153 (10)0.0155 (10)0.0022 (10)
C310.0231 (10)0.0175 (8)0.0178 (9)0.0001 (7)0.0039 (7)0.0035 (7)
C320.0253 (10)0.0199 (8)0.0191 (9)0.0039 (7)0.0078 (8)0.0038 (7)
C330.0220 (10)0.0256 (9)0.0255 (9)0.0025 (7)0.0055 (8)0.0030 (8)
C340.0259 (11)0.0252 (9)0.0243 (10)0.0003 (8)0.0030 (8)0.0005 (8)
C350.0289 (11)0.0235 (9)0.0200 (9)0.0027 (8)0.0066 (8)0.0003 (7)
C360.0255 (10)0.0190 (8)0.0180 (9)0.0013 (7)0.0068 (7)0.0049 (7)
C370.0265 (10)0.0252 (9)0.0185 (9)0.0007 (7)0.0089 (8)0.0015 (7)
C380.0287 (12)0.0439 (12)0.0331 (11)0.0022 (9)0.0049 (9)0.0100 (10)
C410.0239 (10)0.0235 (9)0.0229 (9)0.0011 (7)0.0111 (8)0.0021 (8)
C420.0198 (9)0.0264 (9)0.0214 (9)0.0004 (7)0.0085 (8)0.0017 (7)
C430.0263 (10)0.0285 (9)0.0213 (9)0.0016 (8)0.0080 (8)0.0016 (8)
C440.0307 (11)0.0256 (9)0.0292 (10)0.0019 (8)0.0128 (9)0.0034 (8)
C450.0277 (11)0.0252 (9)0.0287 (10)0.0051 (8)0.0108 (8)0.0034 (8)
C460.0230 (10)0.0299 (10)0.0219 (9)0.0008 (8)0.0077 (8)0.0049 (8)
C470.0279 (11)0.0379 (11)0.0233 (10)0.0066 (9)0.0042 (8)0.0030 (8)
C47A0.0428 (13)0.0534 (13)0.0219 (10)0.0100 (11)0.0076 (9)0.0048 (10)
C47B0.0393 (13)0.0492 (13)0.0314 (11)0.0115 (10)0.0050 (10)0.0095 (10)
C47C0.0327 (12)0.0469 (12)0.0344 (12)0.0012 (10)0.0005 (10)0.0016 (10)
C480.0484 (14)0.0330 (11)0.0362 (12)0.0035 (10)0.0151 (10)0.0045 (10)
N10.0226 (9)0.0210 (7)0.0251 (8)0.0004 (6)0.0051 (7)0.0016 (7)
C10.0244 (10)0.0266 (9)0.0287 (10)0.0019 (8)0.0087 (8)0.0030 (8)
C20.0378 (12)0.0278 (10)0.0391 (12)0.0080 (9)0.0178 (10)0.0067 (9)
C30.0250 (11)0.0274 (9)0.0332 (11)0.0026 (8)0.0116 (9)0.0004 (8)
C40.0382 (12)0.0347 (11)0.0305 (11)0.0011 (9)0.0132 (9)0.0008 (9)
C50.0322 (11)0.0265 (9)0.0249 (10)0.0006 (8)0.0016 (8)0.0006 (8)
C60.0546 (15)0.0267 (10)0.0276 (11)0.0017 (9)0.0114 (10)0.0013 (9)
N20.0545 (14)0.0483 (12)0.0863 (17)0.0048 (10)0.0390 (13)0.0082 (12)
C70.0359 (13)0.0406 (12)0.0664 (16)0.0033 (10)0.0241 (12)0.0072 (12)
C80.0317 (13)0.0416 (12)0.0556 (15)0.0057 (10)0.0201 (11)0.0012 (11)
Geometric parameters (Å, º) top
O1—C111.370 (2)C31—C321.411 (2)
O2—C211.371 (2)C32—C331.393 (3)
O3—C311.360 (2)C33—C341.392 (3)
O4—C411.367 (2)C34—C351.392 (3)
C11—C121.403 (2)C34—C381.514 (3)
C11—C161.410 (2)C35—C361.391 (3)
C12—C131.391 (2)C36—C371.516 (3)
C12—C191.540 (2)C37—C421.518 (2)
C13—C141.400 (3)C41—C421.401 (3)
C14—C151.383 (3)C41—C461.412 (2)
C14—C181.508 (3)C42—C431.390 (2)
C15—C161.384 (2)C43—C441.387 (3)
C16—C171.519 (2)C44—C451.392 (3)
C17—C221.515 (3)C44—C481.513 (3)
C19—C19B1.531 (3)C45—C461.397 (3)
C19—C19A1.531 (3)C46—C471.539 (3)
C19—C19C1.532 (3)C47—C47B1.536 (3)
C21—C261.397 (3)C47—C47C1.537 (3)
C21—C221.404 (2)C47—C47A1.541 (3)
C22—C231.393 (2)N1—C11.498 (2)
C23—C241.399 (3)N1—C51.502 (2)
C24—C251.390 (3)N1—C31.504 (2)
C24—C281.506 (3)C1—C21.510 (3)
C25—C261.393 (2)C3—C41.516 (3)
C26—C271.522 (2)C5—C61.509 (3)
C27—C321.519 (2)N2—C81.142 (3)
C31—C361.407 (2)C7—C81.443 (3)
O1—C11—C12117.48 (15)C33—C32—C31119.28 (16)
O1—C11—C16121.02 (16)C33—C32—C27119.95 (16)
C12—C11—C16121.49 (16)C31—C32—C27120.74 (16)
C13—C12—C11117.08 (16)C34—C33—C32122.30 (17)
C13—C12—C19121.23 (16)C35—C34—C33117.31 (17)
C11—C12—C19121.69 (15)C35—C34—C38121.08 (17)
C12—C13—C14123.04 (17)C33—C34—C38121.59 (17)
C15—C14—C13117.64 (17)C36—C35—C34122.65 (17)
C15—C14—C18122.22 (18)C35—C36—C31119.13 (17)
C13—C14—C18120.13 (18)C35—C36—C37119.86 (15)
C14—C15—C16122.33 (18)C31—C36—C37120.98 (16)
C15—C16—C11118.38 (17)C36—C37—C42114.67 (14)
C15—C16—C17120.14 (16)O4—C41—C42120.70 (16)
C11—C16—C17121.45 (16)O4—C41—C46118.30 (16)
C22—C17—C16113.12 (15)C42—C41—C46120.98 (16)
C19B—C19—C19A107.29 (16)C43—C42—C41118.96 (16)
C19B—C19—C19C110.36 (18)C43—C42—C37120.11 (16)
C19A—C19—C19C107.35 (17)C41—C42—C37120.90 (16)
C19B—C19—C12109.44 (16)C44—C43—C42122.27 (17)
C19A—C19—C12112.18 (16)C43—C44—C45117.21 (17)
C19C—C19—C12110.16 (16)C43—C44—C48121.76 (18)
O2—C21—C26121.53 (16)C45—C44—C48121.03 (17)
O2—C21—C22117.04 (16)C44—C45—C46123.63 (17)
C26—C21—C22121.41 (16)C45—C46—C41116.92 (17)
C23—C22—C21118.23 (17)C45—C46—C47121.49 (16)
C23—C22—C17120.68 (16)C41—C46—C47121.51 (16)
C21—C22—C17121.09 (16)C47B—C47—C47C108.18 (17)
C22—C23—C24121.83 (17)C47B—C47—C46111.41 (16)
C25—C24—C23118.06 (17)C47C—C47—C46108.69 (16)
C25—C24—C28121.43 (18)C47B—C47—C47A106.71 (16)
C23—C24—C28120.51 (18)C47C—C47—C47A110.03 (17)
C24—C25—C26122.20 (18)C46—C47—C47A111.76 (16)
C25—C26—C21118.22 (16)C1—N1—C5113.21 (14)
C25—C26—C27120.21 (17)C1—N1—C3113.87 (14)
C21—C26—C27121.57 (16)C5—N1—C3109.02 (14)
C32—C27—C26114.15 (14)N1—C1—C2113.05 (16)
O3—C31—C36119.85 (16)N1—C3—C4113.66 (16)
O3—C31—C32120.83 (15)N1—C5—C6113.71 (16)
C36—C31—C32119.32 (16)N2—C8—C7179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.96 (3)1.74 (3)2.684 (2)166 (2)
O2—H2···O31.04 (3)1.46 (3)2.499 (2)177 (2)
O4—H4···O31.00 (3)1.68 (3)2.666 (2)167 (2)
N1—H3···O3i0.98 (3)1.70 (3)2.671 (3)170 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC6H16N+·C39H47O4·C2H3N
Mr723.02
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)16.024 (3), 17.073 (3), 16.067 (3)
β (°) 106.75 (3)
V3)4209.1 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.2 × 0.2 × 0.15
Data collection
DiffractometerNonius CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15352, 8472, 5631
Rint0.046
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.123, 1.00
No. of reflections8472
No. of parameters508
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.19

Computer programs: DENZO (Otwinowski & Minor, 1997), DENZO, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.96 (3)1.74 (3)2.684 (2)166 (2)
O2—H2···O31.04 (3)1.46 (3)2.499 (2)177 (2)
O4—H4···O31.00 (3)1.68 (3)2.666 (2)167 (2)
N1—H3···O3i0.98 (3)1.70 (3)2.671 (3)170 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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