research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 399-402
doi:10.1107/S2056989016002899

Bis(benzyl­tri­methyl­ammonium) bis­­[(4SR,12SR,18RS,26RS)-4,18,26-trihy­dr­oxy-12-oxido-13,17-dioxahepta­cyclo­[14.10.0.03,14.04,12.06,11.018,26.019,24]hexa­cosa-1,3(14),6,8,10,15,19,21,23-nona­ene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]− negative charge-assisted hydrogen bonds (–CAHB) with benzyl­tri­methyl­ammonium counter-ions

CROSSMARK_Color_square_no_text.svg
Ravell Bengiat,a Maayan Gil,a Asne Klein,a Benny Bogoslavsky,a Shmuel Cohena and Joseph Almoga*

aThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, Israel
*Correspondence e-mail: almog@mail.huji.ac.il

Edited by A. J. Lough, University of Toronto, Canada (Received 26 January 2016; accepted 17 February 2016; online 24 February 2016)

The reaction between bis-ninhydrin resorcinol and benzyl­tri­methyl­ammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8−·1.5H2O, which contains a unique centrosymmetric supra­molecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395 (13) Å] [O—H—O]− bonds of the type negative charge-assisted hydrogen bonds (–CAHB). The central aromatic rings of the ligands create parallel-displaced π–π stacking at an inter­planar distance of 3.381 (1) Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water mol­ecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O—H⋯O hydrogen bonds, forming chains along [101].

CCDC reference: 1449570

1. Chemical context

The vasarene family consists of self-assembled, vase-shaped compounds and their analogues, which are prepared by a one-pot reaction between cyclic vicinal polycarbonyl compounds and polyhy­droxy aromatics (Na et al., 2005[Na, J. E., Lee, K. Y., Seo, J. & Kim, J. N. (2005). Tetrahedron Lett. 46, 4505-4508.]; Almog et al., 2009[Almog, J., Rozin, R., Klein, A., Shamuilov-Levinton, G. & Cohen, S. (2009). Tetrahedron, 65, 7954-7962.]). The supra­molecular behaviors of these structures have been an ongoing study in our group, particularly their intriguing feature of selective affinity towards ion-pairs of type M+F−, M being a large monovalent cation (Almog et al., 2012[Almog, J., Gavish-Abramovich, I., Rozin, R., Cohen, S., Yardeni, G. & Zilbermann, I. (2012). Eur. J. Inorg. Chem. pp. 4427-4432.]). A recent study has shown that the multiple oxygen-containing functional groups of these ligands (hemiketals, carbonyls and hydroxyls) play a key role in this supra­molecular binding mechanism by forming dimeric entities via strong [O—H—O]− hydrogen-bonding (Bengiat et al., 2016[Bengiat, R., Gil, M., Klein, A., Bogoslavsky, B., Cohen, S., Dubnikov, F., Yardeni, G., Zilbermann, I. & Almog, J. (2016). Dalton Trans. doi: 10.1039/C5DT04171F.]).

2. Structural commentary

The dimer was formed following the reaction of bis ninhydrin resorcinol (1) with benzyl­tri­methyl­ammonium fluoride, in which the fluoride acted as a base removing a proton from the hemiketal hydroxyl group (Scheme). Several factors help in stabilizing this dimeric entity. The first is the π–π stacking of the middle aromatic rings that are parallel-displaced but could almost be considered as a `sandwich' conformation due to the minor angle of displacement (15°). The inter­planar distance between the two rings is also quite short [3.381 (1) Å] supporting the strength of this inter­action (Janiak, 2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]).

[Scheme 1]

The two [O—H—O]− negative charge-assisted hydrogen bonds (CAHB), although deviating from linearity [164 (2)°], are still considerably strong and short – with an O⋯O distance of 2.4395 (13) Å, corresponding to low-barrier hydrogen bonds (LBHB) (Cleland et al., 1998[Cleland, W. W., Frey, P. A. & Gerlt, J. A. (1998). J. Biol. Chem. 273, 25529-25532.]). Additional hydrogen bonding (Table 1[link]) between the remaining hydroxyl groups O7—H7O, O3—H3O and the etheric hemiketal oxygen atoms O1 and O5, respectively, assist in stabilizing the dimer (Fig. 1[link]). Fig. 2[link] shows that the steric benzyl groups of the cations remain beside the ligands and parallel to each other, with two water mol­ecules hydrogen bonded to the carbonyl groups on the ligands (O1W—H2W1⋯O8). Two cell units also display parallel-displaced π–π stacking between the aromatic rings of the `side-walls' of the ligands with an inter­planar distance of 3.349 (1) Å (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H2W1⋯O8 1.00 1.94 2.898 (2) 160
O1W—H1W1⋯O4i 1.03 2.00 3.028 (2) 174
O7—H7O⋯O1ii 0.94 (2) 1.85 (2) 2.7818 (14) 171.7 (18)
O3—H3O⋯O5ii 0.942 (19) 1.942 (19) 2.8796 (14) 173.2 (17)
O2—H2O⋯O6ii 1.23 (2) 1.23 (2) 2.4395 (13) 164 (2)
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1.
[Figure 1]
Figure 1
ORTEP drawing of the bis ninhydrin resorcinol (1) dimer showing 50% probability ellipsoids for non-H atoms. The cations, solvent mol­ecules and aromatic hydrogen atoms have been removed for clarity. [Symmetry code: (i): −x + 1, −y + 1, −z + 1.]
[Figure 2]
Figure 2
ORTEP drawing of the complex showing 50% probability ellipsoids for non-H atoms (side-view). The aromatic and aliphatic hydrogen atoms have been removed for clarity. [Symmetry code: (i): −x + 1, −y + 1, −z + 1.]
[Figure 3]
Figure 3
The parallel-displaced π–π stacking between two aromatic rings on the `side-walls' of the ligands of two different cell units showing the inter­planar distance between the rings. The cations, solvent mol­ecules and aromatic hydrogen atoms have been removed for clarity.

3. Database survey

A survey of the Cambridge Structural Database (Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) revealed nineteen occurrences of organic compounds containing a similar motif of a negative charge-assisted hydrogen bond (CAHB) of the type [O—H—O]− connecting two carbon atoms. Among them, the shortest O⋯O distances specified range from 2.457 Å (Barczyński et al., 2006[Barczyński, P., Komasa, A., Ratajczak-Sitarz, M., Katrusiak, A. & Brzezinski, B. (2006). J. Mol. Struct. 800, 135-139.]), 2.446 Å (Pan et al., 1996[Pan, F., Wong, M. S., Gramlich, V., Bosshard, C. & Gunter, P. (1996). Chem. Commun. pp. 1557-1558.]), 2.437 Å (Polyakova et al., 1983[Polyakova, I. N., Starikova, Z. A., Parusnikov, B. V. & Krasavin, I. A. (1983). Sov. Phys. Crystallogr. 28, 50-53.]) to 2.430 Å (Yang et al., 2010[Yang, Y., Li, K., Luo, S. & Li, Q. (2010). J. Mol. Struct. 969, 83-87.]). However, a recent study in our group revealed a much shorter O⋯O distance of 2.404 (3) Å when a completely different dimeric entity was formed in the reaction of (1) with tetra­methyl­ammonium fluoride (Bengiat et al., 2016[Bengiat, R., Gil, M., Klein, A., Bogoslavsky, B., Cohen, S., Dubnikov, F., Yardeni, G., Zilbermann, I. & Almog, J. (2016). Dalton Trans. doi: 10.1039/C5DT04171F.]).

4. Synthesis and crystallization

The ligand (1) was prepared by a one-pot synthesis as described in a previously reported procedure (Bengiat et al., 2016[Bengiat, R., Gil, M., Klein, A., Bogoslavsky, B., Cohen, S., Dubnikov, F., Yardeni, G., Zilbermann, I. & Almog, J. (2016). Dalton Trans. doi: 10.1039/C5DT04171F.]). Bis ninhydrin resorcinol (1) (300 mg, 0.7 mmol) was dissolved in hot ethanol (10 mL) and a few drops of water. BnN(Me)3F·H2O (255 mg, 1.4 mmol) was dissolved in hot ethanol (2 mL). Upon addition of the salt solution to the solution of (1), an immediate colour change to intense yellow was observed. A colourless crystalline precipitate was formed after approximately 24 h at RT suitable for single crystal X-ray crystallography.

5. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The site occupancy of the water was set at 0.75 during the refinement process, as when defining a value of 1 the R-factor increased considerably by 0.7%. Hydroxyl H atoms of the ligand mol­ecules and H atoms of the water mol­ecule were located in a different Fourier map and all H-atom parameters were refined except for those of the water mol­ecule for which only the U-parameters were refined. Other H atoms were placed in calculated positions with C—H = 0.93 (aromatic) and 0.96 A (meth­yl), and refined in a riding-model approximation with Uiso(H) = 1.2Ueq(C) for aromatic and aliphatic H atoms and 1.5Ueq(C) for the methyl H atoms.

Table 2
Experimental details

Crystal data
Chemical formula 2C10H16N+·2C24H13O8−·1.5H2O
Mr 1186.19
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 10.934 (2), 11.088 (2), 12.402 (2)
α, β, γ (°) 102.873 (3), 106.083 (3), 95.548 (3)
V (Å3) 1388.0 (4)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.31 × 0.19 × 0.15
 
Data collection
Diffractometer Bruker SMART CCD
Absorption correction Multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.969, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections 15809, 5990, 4702
Rint 0.068
(sin θ/λ)max (Å−1) 0.639
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.108, 0.99
No. of reflections 5990
No. of parameters 414
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.26, −0.42
Computer programs: SMART and SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Supporting information

CCDC reference: 1449570

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989016002899/lh5804sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016002899/lh5804Isup2.hkl

checkCIF report


Chemical context top

The vasarene family consists of self-assembled, vase-shaped compounds and their analogues, which are prepared by a one-pot reaction between cyclic vicinal polycarbonyl compounds and polyhy­droxy aromatics (Na et al., 2005; Almog et al., 2009). The supra­molecular behaviors of these structures have been an ongoing study in our group, particularly their intriguing feature of selective affinity towards ion-pairs of type M+F−, M being a large monovalent cation (Almog et al., 2012). A recent study has shown that the multiple oxygen-containing functional groups of these ligands (hemiketals, carbonyls and hydroxyls) play a key role in this supra­molecular binding mechanism by forming dimeric entities via strong [O—H—O]− hydrogen-bonding (Bengiat et al., 2016).

Structural commentary top

The dimer was formed following the reaction of bis ninhydrin resorcinol (1) with benzyl­tri­methyl­ammonium fluoride, in which the fluoride acted as a base removing a proton from the hemiketal hydroxyl group (Scheme). Several factors help in stabilizing this dimeric entity. The first is the π–π stacking of the middle aromatic rings that are parallel-displaced but could almost be considered as a `sandwich' conformation due to the minor angle of displacement (15°). The inter­planar distance between the two rings is also quite short [3.381 (1) Å] supporting the strength of this inter­action (Janiak, 2000). The two [O—H—O]− negative charge-assisted hydrogen bonds (CAHB), although deviating from linearity [164 (2)°], are still considerably strong and short – with an O···O distance of 2.4395 (13) Å, corresponding to low-barrier hydrogen bonds (LBHB) (Cleland et al., 1998). Additional hydrogen bonding between the remaining hydroxyl groups O7—H7O, O3—H3O and the etheric hemiketal oxygen atoms O1 and O5, respectively, assist in stabilizing the dimer (Fig. 1). Fig. 2 shows that the steric benzyl groups of the cations remain beside the ligands and parallel to each other, with two water molecules hydrogen bonded to the carbonyl groups on the ligands (O1W—H2W1···O8). Two cell units also display parallel-displaced π–π stacking between the aromatic rings of the `side-walls' of the ligands with a an inter­planar distance of 3.349 (1) Å (Fig. 3).

Database survey top

A survey of the Cambridge Structural Database (Groom & Allen, 2014) revealed nineteen occurrences of organic compounds containing a similar motif of a negative charge-assisted hydrogen bond (CAHB) of the type [O—H—O]− connecting two carbon atoms. Among them, the shortest O···O distances specified range from 2.457 Å (Barczyński et al., 2006), 2.446 Å (Pan et al., 1996), 2.437 Å (Polyakova et al., 1983) to 2.430 Å (Yang et al., 2010). However, a recent study in our group revealed a much shorter O···O distance of 2.404 (3) Å when a completely different dimeric entity was formed in the reaction of (1) with tetra­methyl­ammonium fluoride (Bengiat et al., 2016).

Synthesis and crystallization top

The ligand (1) was prepared by a one-pot synthesis as described in a previously reported procedure (Bengiat et al., 2016). Bis ninhydrin resorcinol (1) (300 mg, 0.7 mmol) was dissolved in hot ethanol (~10 ml) and few drops of water. BnN(Me)3F·H2O (255 mg, 1.4 mmol) was dissolved in hot ethanol (2 ml). Upon addition of the salt solution to the solution of (1), an immediate colour change to intense yellow was observed. A colourless crystalline precipitate was formed after approximately 24 h at RT suitable for single-crystal X-ray crystallography.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The site occupancy of the water was set at 0.75 during the refinement process, as when defining a value of 1 the R-factor increased considerably by 0.7%. Hydroxyl H atoms of the ligand molecules and H atoms of the water molecule were located in a different Fourier map and all H-atom parameters were refined except for the water molecule for which only the U-parameters were refined. Other H atoms were placed in calculated positions with C—H = 0.93 (aromatic) and 0.96 A (methyl), and refined in a riding-model approximation with Uiso(H) = 1.2Ueq(C) for aromatic and aliphatic H atoms and 1.5Ueq(C) for the methyl H atoms.

Structure description top

The vasarene family consists of self-assembled, vase-shaped compounds and their analogues, which are prepared by a one-pot reaction between cyclic vicinal polycarbonyl compounds and polyhy­droxy aromatics (Na et al., 2005; Almog et al., 2009). The supra­molecular behaviors of these structures have been an ongoing study in our group, particularly their intriguing feature of selective affinity towards ion-pairs of type M+F−, M being a large monovalent cation (Almog et al., 2012). A recent study has shown that the multiple oxygen-containing functional groups of these ligands (hemiketals, carbonyls and hydroxyls) play a key role in this supra­molecular binding mechanism by forming dimeric entities via strong [O—H—O]− hydrogen-bonding (Bengiat et al., 2016).

The dimer was formed following the reaction of bis ninhydrin resorcinol (1) with benzyl­tri­methyl­ammonium fluoride, in which the fluoride acted as a base removing a proton from the hemiketal hydroxyl group (Scheme). Several factors help in stabilizing this dimeric entity. The first is the π–π stacking of the middle aromatic rings that are parallel-displaced but could almost be considered as a `sandwich' conformation due to the minor angle of displacement (15°). The inter­planar distance between the two rings is also quite short [3.381 (1) Å] supporting the strength of this inter­action (Janiak, 2000). The two [O—H—O]− negative charge-assisted hydrogen bonds (CAHB), although deviating from linearity [164 (2)°], are still considerably strong and short – with an O···O distance of 2.4395 (13) Å, corresponding to low-barrier hydrogen bonds (LBHB) (Cleland et al., 1998). Additional hydrogen bonding between the remaining hydroxyl groups O7—H7O, O3—H3O and the etheric hemiketal oxygen atoms O1 and O5, respectively, assist in stabilizing the dimer (Fig. 1). Fig. 2 shows that the steric benzyl groups of the cations remain beside the ligands and parallel to each other, with two water molecules hydrogen bonded to the carbonyl groups on the ligands (O1W—H2W1···O8). Two cell units also display parallel-displaced π–π stacking between the aromatic rings of the `side-walls' of the ligands with a an inter­planar distance of 3.349 (1) Å (Fig. 3).

A survey of the Cambridge Structural Database (Groom & Allen, 2014) revealed nineteen occurrences of organic compounds containing a similar motif of a negative charge-assisted hydrogen bond (CAHB) of the type [O—H—O]− connecting two carbon atoms. Among them, the shortest O···O distances specified range from 2.457 Å (Barczyński et al., 2006), 2.446 Å (Pan et al., 1996), 2.437 Å (Polyakova et al., 1983) to 2.430 Å (Yang et al., 2010). However, a recent study in our group revealed a much shorter O···O distance of 2.404 (3) Å when a completely different dimeric entity was formed in the reaction of (1) with tetra­methyl­ammonium fluoride (Bengiat et al., 2016).

Synthesis and crystallization top

The ligand (1) was prepared by a one-pot synthesis as described in a previously reported procedure (Bengiat et al., 2016). Bis ninhydrin resorcinol (1) (300 mg, 0.7 mmol) was dissolved in hot ethanol (~10 ml) and few drops of water. BnN(Me)3F·H2O (255 mg, 1.4 mmol) was dissolved in hot ethanol (2 ml). Upon addition of the salt solution to the solution of (1), an immediate colour change to intense yellow was observed. A colourless crystalline precipitate was formed after approximately 24 h at RT suitable for single-crystal X-ray crystallography.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The site occupancy of the water was set at 0.75 during the refinement process, as when defining a value of 1 the R-factor increased considerably by 0.7%. Hydroxyl H atoms of the ligand molecules and H atoms of the water molecule were located in a different Fourier map and all H-atom parameters were refined except for the water molecule for which only the U-parameters were refined. Other H atoms were placed in calculated positions with C—H = 0.93 (aromatic) and 0.96 A (methyl), and refined in a riding-model approximation with Uiso(H) = 1.2Ueq(C) for aromatic and aliphatic H atoms and 1.5Ueq(C) for the methyl H atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the bis ninhydrin resorcinol (1) dimer showing 50% probability ellipsoids for non-H atoms. The cations, solvent molecules and aromatic hydrogen atoms have been removed for clarity. [Symmetry code: (i): −x + 1, −y + 1, −z + 1.]
[Figure 2] Fig. 2. ORTEP drawing of the complex showing 50% probability ellipsoids for non-H atoms (side-view). The aromatic and aliphatic hydrogen atoms have been removed for clarity. [Symmetry code: (i): −x + 1, −y + 1, −z + 1.]
[Figure 3] Fig. 3. The parallel-displaced π–π stacking between two aromatic rings on the `side-walls' of the ligands of two different cell units showing the interplanar distance between the rings. The cations, solvent molecules and aromatic hydrogen atoms have been removed for clarity.
Bis(benzyltrimethylazanium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate top
Crystal data top
2C10H16N+·2C24H13O8−·1.5H2OZ = 1
Mr = 1186.19F(000) = 627
Triclinic, P1Dx = 1.419 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.934 (2) ÅCell parameters from 5453 reflections
b = 11.088 (2) Åθ = 2.5–28.0°
c = 12.402 (2) ŵ = 0.10 mm−1
α = 102.873 (3)°T = 173 K
β = 106.083 (3)°Prism, colourless
γ = 95.548 (3)°0.31 × 0.19 × 0.15 mm
V = 1388.0 (4) Å3
Data collection top
Bruker SMART CCD
diffractometer		5990 independent reflections
Radiation source: fine-focus sealed tube4702 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
φ and ω scansθmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −13→13
Tmin = 0.969, Tmax = 0.985k = −14→14
15809 measured reflectionsl = −15→15
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0623P)2]
where P = (Fo2 + 2Fc2)/3
5990 reflections(Δ/σ)max < 0.001
414 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
2C10H16N+·2C24H13O8−·1.5H2Oγ = 95.548 (3)°
Mr = 1186.19V = 1388.0 (4) Å3
Triclinic, P1Z = 1
a = 10.934 (2) ÅMo Kα radiation
b = 11.088 (2) ŵ = 0.10 mm−1
c = 12.402 (2) ÅT = 173 K
α = 102.873 (3)°0.31 × 0.19 × 0.15 mm
β = 106.083 (3)°
Data collection top
Bruker SMART CCD
diffractometer		5990 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		4702 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.985Rint = 0.068
15809 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.26 e Å−3
5990 reflectionsΔρmin = −0.42 e Å−3
414 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.54556 (12)0.38574 (12)0.37869 (11)0.0210 (3)
H10.60940.33510.39830.025*
C20.41599 (12)0.34619 (11)0.36199 (11)0.0200 (3)
C30.32002 (12)0.41652 (12)0.32952 (11)0.0204 (3)
C40.35280 (12)0.53425 (12)0.31428 (11)0.0214 (3)
H40.28840.58300.29100.026*
C50.48258 (12)0.57893 (11)0.33408 (11)0.0205 (3)
C60.57524 (12)0.50447 (12)0.36475 (11)0.0195 (3)
C70.22477 (12)0.20971 (12)0.32385 (11)0.0226 (3)
C80.18957 (12)0.34289 (12)0.31418 (12)0.0228 (3)
C90.10582 (13)0.31815 (14)0.18729 (12)0.0287 (3)
C100.13239 (13)0.20071 (13)0.12196 (12)0.0293 (3)
C110.19725 (13)0.13783 (13)0.19887 (12)0.0257 (3)
C120.23375 (14)0.02396 (13)0.15819 (13)0.0321 (3)
H120.2773−0.02010.21060.039*
C130.20496 (16)−0.02342 (16)0.03952 (14)0.0408 (4)
H130.2289−0.10130.01030.049*
C140.14213 (16)0.03992 (16)−0.03785 (14)0.0441 (4)
H140.12570.0062−0.11890.053*
C150.10309 (15)0.15168 (16)0.00167 (13)0.0400 (4)
H150.05760.1942−0.05120.048*
C160.69013 (13)0.67546 (12)0.33598 (12)0.0231 (3)
C170.54794 (12)0.70177 (12)0.32628 (11)0.0229 (3)
C180.49527 (14)0.71739 (13)0.20351 (13)0.0294 (3)
C190.58105 (14)0.66924 (13)0.13771 (12)0.0314 (3)
C200.68852 (13)0.63946 (12)0.21048 (12)0.0271 (3)
C210.77956 (15)0.58588 (14)0.16508 (14)0.0371 (4)
H210.85170.56180.21330.045*
C220.76163 (19)0.56874 (17)0.04711 (15)0.0517 (5)
H220.82340.53360.01460.062*
C230.6554 (2)0.60174 (17)−0.02442 (15)0.0544 (5)
H230.64650.5905−0.10460.065*
C240.56311 (18)0.65039 (15)0.01930 (14)0.0447 (4)
H240.48900.6707−0.02990.054*
C250.21050 (13)0.88120 (12)0.64347 (12)0.0254 (3)
C260.32821 (14)0.96261 (13)0.69602 (13)0.0326 (3)
H260.35021.02710.66210.039*
C270.41277 (15)0.95013 (15)0.79668 (14)0.0397 (4)
H270.49251.00630.83210.048*
C280.38232 (16)0.85660 (15)0.84619 (14)0.0411 (4)
H280.44130.84800.91540.049*
C290.26592 (16)0.77517 (14)0.79522 (14)0.0378 (4)
H290.24530.71020.82910.045*
C300.17950 (14)0.78800 (13)0.69508 (13)0.0308 (3)
H300.09880.73310.66140.037*
C310.11721 (13)0.89919 (13)0.53629 (12)0.0259 (3)
H31A0.13000.98940.53840.031*
H31B0.02830.87580.53830.031*
C320.26207 (13)0.85536 (14)0.41394 (14)0.0315 (3)
H32A0.32420.82830.47370.047*
H32B0.28390.94620.42620.047*
H32C0.26510.81210.33690.047*
C330.09611 (14)0.68618 (12)0.40874 (13)0.0308 (3)
H33A0.09400.63950.33100.046*
H33B0.01130.66780.41920.046*
H33C0.16160.66120.46750.046*
C340.03461 (13)0.85805 (13)0.32406 (12)0.0284 (3)
H34A0.05620.94770.33040.043*
H34B−0.05300.83970.32870.043*
H34C0.03910.80900.24940.043*
N10.12893 (10)0.82394 (10)0.42162 (10)0.0243 (3)
O10.37059 (8)0.23328 (8)0.37546 (8)0.0231 (2)
O20.17312 (9)0.15028 (8)0.38748 (8)0.0260 (2)
H2O0.205 (2)0.203 (2)0.492 (2)0.087 (7)*
O30.12328 (9)0.39817 (9)0.38979 (9)0.0269 (2)
H3O0.1761 (18)0.4133 (17)0.4673 (17)0.057 (6)*
O40.03367 (10)0.38624 (11)0.15004 (10)0.0428 (3)
O50.69830 (8)0.55906 (8)0.38039 (8)0.0235 (2)
O60.78933 (8)0.76444 (8)0.40482 (8)0.0256 (2)
O70.53759 (9)0.80979 (8)0.40608 (9)0.0266 (2)
H7O0.5749 (19)0.8019 (18)0.4813 (17)0.063 (6)*
O80.39802 (10)0.76058 (10)0.16867 (10)0.0417 (3)
O1W0.12255 (16)0.67396 (15)0.10433 (14)0.0505 (4)0.75
H1W10.07500.65730.01680.113 (12)*0.75
H2W10.21140.71010.10910.139 (15)*0.75
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0197 (7)0.0215 (7)0.0215 (7)0.0040 (5)0.0061 (5)0.0051 (5)
C20.0237 (7)0.0175 (6)0.0182 (6)−0.0004 (5)0.0071 (5)0.0041 (5)
C30.0181 (6)0.0213 (7)0.0205 (7)−0.0002 (5)0.0068 (5)0.0032 (5)
C40.0201 (7)0.0211 (7)0.0240 (7)0.0039 (5)0.0075 (5)0.0066 (5)
C50.0218 (7)0.0190 (6)0.0213 (7)0.0013 (5)0.0082 (5)0.0057 (5)
C60.0176 (6)0.0226 (7)0.0171 (6)−0.0001 (5)0.0068 (5)0.0027 (5)
C70.0188 (6)0.0220 (7)0.0248 (7)−0.0023 (5)0.0063 (5)0.0043 (5)
C80.0192 (7)0.0229 (7)0.0269 (7)0.0008 (5)0.0093 (6)0.0063 (6)
C90.0196 (7)0.0353 (8)0.0316 (8)−0.0019 (6)0.0059 (6)0.0146 (7)
C100.0246 (7)0.0318 (8)0.0265 (7)−0.0076 (6)0.0056 (6)0.0057 (6)
C110.0224 (7)0.0265 (7)0.0255 (7)−0.0064 (5)0.0091 (6)0.0038 (6)
C120.0343 (8)0.0291 (8)0.0317 (8)−0.0027 (6)0.0145 (7)0.0032 (6)
C130.0462 (10)0.0368 (9)0.0354 (9)−0.0046 (7)0.0201 (8)−0.0035 (7)
C140.0488 (10)0.0472 (10)0.0258 (8)−0.0119 (8)0.0134 (8)−0.0053 (7)
C150.0346 (9)0.0499 (10)0.0284 (8)−0.0099 (7)0.0036 (7)0.0111 (7)
C160.0232 (7)0.0213 (7)0.0254 (7)−0.0008 (5)0.0095 (6)0.0064 (6)
C170.0214 (7)0.0211 (7)0.0268 (7)0.0004 (5)0.0086 (6)0.0072 (6)
C180.0287 (8)0.0232 (7)0.0323 (8)−0.0062 (6)0.0031 (6)0.0117 (6)
C190.0375 (8)0.0266 (7)0.0264 (8)−0.0099 (6)0.0083 (6)0.0080 (6)
C200.0292 (7)0.0229 (7)0.0268 (7)−0.0087 (6)0.0123 (6)0.0029 (6)
C210.0343 (8)0.0345 (8)0.0376 (9)−0.0103 (7)0.0188 (7)−0.0034 (7)
C220.0559 (12)0.0501 (11)0.0416 (10)−0.0213 (9)0.0326 (9)−0.0128 (8)
C230.0715 (14)0.0554 (11)0.0250 (9)−0.0299 (10)0.0201 (9)−0.0012 (8)
C240.0578 (11)0.0409 (9)0.0279 (8)−0.0188 (8)0.0085 (8)0.0113 (7)
C250.0244 (7)0.0232 (7)0.0300 (8)0.0055 (5)0.0116 (6)0.0055 (6)
C260.0310 (8)0.0284 (8)0.0367 (9)−0.0012 (6)0.0090 (7)0.0095 (6)
C270.0307 (8)0.0411 (9)0.0403 (9)−0.0018 (7)0.0041 (7)0.0082 (7)
C280.0431 (10)0.0420 (9)0.0354 (9)0.0132 (8)0.0050 (7)0.0113 (7)
C290.0516 (10)0.0312 (8)0.0356 (9)0.0081 (7)0.0185 (8)0.0121 (7)
C300.0318 (8)0.0271 (8)0.0343 (8)0.0011 (6)0.0150 (7)0.0053 (6)
C310.0238 (7)0.0234 (7)0.0309 (8)0.0053 (5)0.0109 (6)0.0041 (6)
C320.0233 (7)0.0334 (8)0.0404 (9)0.0050 (6)0.0147 (6)0.0087 (7)
C330.0310 (8)0.0213 (7)0.0392 (9)0.0046 (6)0.0111 (7)0.0058 (6)
C340.0267 (7)0.0279 (7)0.0303 (8)0.0050 (6)0.0078 (6)0.0079 (6)
N10.0219 (6)0.0213 (6)0.0304 (6)0.0041 (4)0.0101 (5)0.0053 (5)
O10.0214 (5)0.0194 (5)0.0282 (5)−0.0004 (4)0.0070 (4)0.0079 (4)
O20.0290 (5)0.0225 (5)0.0262 (5)−0.0042 (4)0.0116 (4)0.0057 (4)
O30.0209 (5)0.0288 (5)0.0330 (6)0.0037 (4)0.0123 (4)0.0070 (4)
O40.0339 (6)0.0509 (7)0.0441 (7)0.0119 (5)0.0050 (5)0.0203 (6)
O50.0175 (5)0.0244 (5)0.0298 (5)0.0005 (4)0.0083 (4)0.0092 (4)
O60.0217 (5)0.0266 (5)0.0252 (5)−0.0055 (4)0.0085 (4)0.0025 (4)
O70.0278 (5)0.0209 (5)0.0325 (6)0.0038 (4)0.0115 (4)0.0073 (4)
O80.0354 (6)0.0400 (6)0.0465 (7)0.0040 (5)0.0002 (5)0.0215 (5)
O1W0.0470 (10)0.0568 (11)0.0468 (10)0.0171 (8)0.0124 (8)0.0105 (8)
Geometric parameters (Å, º) top
C1—C61.3850 (18)C20—C211.392 (2)
C1—C21.3853 (18)C21—C221.387 (2)
C1—H10.9500C21—H210.9500
C2—O11.3640 (15)C22—C231.388 (3)
C2—C31.3912 (18)C22—H220.9500
C3—C41.3875 (17)C23—C241.372 (3)
C3—C81.5141 (17)C23—H230.9500
C4—C51.3915 (18)C24—H240.9500
C4—H40.9500C25—C301.3927 (19)
C5—C61.3932 (18)C25—C261.3944 (19)
C5—C171.5113 (17)C25—C311.501 (2)
C6—O51.3638 (15)C26—C271.377 (2)
C7—O21.3351 (15)C26—H260.9500
C7—C111.5076 (18)C27—C281.376 (2)
C7—O11.5164 (16)C27—H270.9500
C7—C81.5832 (19)C28—C291.383 (2)
C8—O31.4095 (16)C28—H280.9500
C8—C91.533 (2)C29—C301.382 (2)
C9—O41.2143 (17)C29—H290.9500
C9—C101.473 (2)C30—H300.9500
C10—C111.384 (2)C31—N11.5258 (17)
C10—C151.401 (2)C31—H31A0.9900
C11—C121.390 (2)C31—H31B0.9900
C12—C131.381 (2)C32—N11.4977 (17)
C12—H120.9500C32—H32A0.9800
C13—C141.383 (2)C32—H32B0.9800
C13—H130.9500C32—H32C0.9800
C14—C151.380 (2)C33—N11.4969 (17)
C14—H140.9500C33—H33A0.9800
C15—H150.9500C33—H33B0.9800
C16—O61.3354 (15)C33—H33C0.9800
C16—C201.5129 (19)C34—N11.5028 (17)
C16—O51.5129 (16)C34—H34A0.9800
C16—C171.5863 (19)C34—H34B0.9800
C17—O71.4095 (16)C34—H34C0.9800
C17—C181.5268 (19)O2—H2O1.23 (2)
C18—O81.2176 (18)O3—H3O0.942 (19)
C18—C191.469 (2)O7—H7O0.94 (2)
C19—C201.387 (2)O1W—H1W11.0305
C19—C241.391 (2)O1W—H2W10.9954
C6—C1—C2115.06 (12)C19—C20—C21120.14 (14)
C6—C1—H1122.5C19—C20—C16111.59 (12)
C2—C1—H1122.5C21—C20—C16128.26 (14)
O1—C2—C1122.70 (11)C22—C21—C20117.91 (17)
O1—C2—C3113.62 (11)C22—C21—H21121.0
C1—C2—C3123.68 (11)C20—C21—H21121.0
C4—C3—C2119.77 (11)C21—C22—C23121.45 (17)
C4—C3—C8130.61 (12)C21—C22—H22119.3
C2—C3—C8109.60 (11)C23—C22—H22119.3
C3—C4—C5118.19 (12)C24—C23—C22120.76 (16)
C3—C4—H4120.9C24—C23—H23119.6
C5—C4—H4120.9C22—C23—H23119.6
C4—C5—C6120.08 (11)C23—C24—C19118.16 (17)
C4—C5—C17130.64 (12)C23—C24—H24120.9
C6—C5—C17109.28 (11)C19—C24—H24120.9
O5—C6—C1122.80 (11)C30—C25—C26118.93 (13)
O5—C6—C5114.02 (11)C30—C25—C31121.26 (13)
C1—C6—C5123.18 (12)C26—C25—C31119.74 (12)
O2—C7—C11115.13 (11)C27—C26—C25120.43 (14)
O2—C7—O1108.79 (10)C27—C26—H26119.8
C11—C7—O1105.41 (10)C25—C26—H26119.8
O2—C7—C8118.43 (11)C28—C27—C26120.30 (15)
C11—C7—C8103.28 (10)C28—C27—H27119.8
O1—C7—C8104.59 (9)C26—C27—H27119.8
O3—C8—C3115.28 (11)C27—C28—C29119.98 (15)
O3—C8—C9110.33 (11)C27—C28—H28120.0
C3—C8—C9108.89 (11)C29—C28—H28120.0
O3—C8—C7116.10 (10)C30—C29—C28120.19 (14)
C3—C8—C7101.74 (10)C30—C29—H29119.9
C9—C8—C7103.55 (11)C28—C29—H29119.9
O4—C9—C10127.80 (14)C29—C30—C25120.15 (14)
O4—C9—C8124.84 (14)C29—C30—H30119.9
C10—C9—C8107.35 (12)C25—C30—H30119.9
C11—C10—C15120.83 (14)C25—C31—N1115.06 (11)
C11—C10—C9109.58 (12)C25—C31—H31A108.5
C15—C10—C9129.59 (14)N1—C31—H31A108.5
C10—C11—C12120.58 (13)C25—C31—H31B108.5
C10—C11—C7112.22 (12)N1—C31—H31B108.5
C12—C11—C7127.15 (13)H31A—C31—H31B107.5
C13—C12—C11118.21 (15)N1—C32—H32A109.5
C13—C12—H12120.9N1—C32—H32B109.5
C11—C12—H12120.9H32A—C32—H32B109.5
C12—C13—C14121.56 (15)N1—C32—H32C109.5
C12—C13—H13119.2H32A—C32—H32C109.5
C14—C13—H13119.2H32B—C32—H32C109.5
C15—C14—C13120.61 (15)N1—C33—H33A109.5
C15—C14—H14119.7N1—C33—H33B109.5
C13—C14—H14119.7H33A—C33—H33B109.5
C14—C15—C10118.19 (15)N1—C33—H33C109.5
C14—C15—H15120.9H33A—C33—H33C109.5
C10—C15—H15120.9H33B—C33—H33C109.5
O6—C16—C20113.58 (11)N1—C34—H34A109.5
O6—C16—O5108.52 (10)N1—C34—H34B109.5
C20—C16—O5107.80 (10)H34A—C34—H34B109.5
O6—C16—C17118.43 (11)N1—C34—H34C109.5
C20—C16—C17103.05 (11)H34A—C34—H34C109.5
O5—C16—C17104.69 (9)H34B—C34—H34C109.5
O7—C17—C5115.40 (11)C33—N1—C32110.29 (11)
O7—C17—C18108.63 (11)C33—N1—C34108.61 (10)
C5—C17—C18109.95 (10)C32—N1—C34108.39 (11)
O7—C17—C16115.99 (11)C33—N1—C31110.40 (11)
C5—C17—C16101.85 (10)C32—N1—C31110.87 (10)
C18—C17—C16104.34 (11)C34—N1—C31108.21 (10)
O8—C18—C19127.60 (14)C2—O1—C7107.53 (9)
O8—C18—C17124.73 (14)C7—O2—H2O115.4 (10)
C19—C18—C17107.66 (12)C8—O3—H3O109.4 (12)
C20—C19—C24121.51 (15)C6—O5—C16107.49 (9)
C20—C19—C18110.42 (12)C17—O7—H7O108.1 (12)
C24—C19—C18128.06 (15)H1W1—O1W—H2W1101.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O81.001.942.898 (2)160
O1W—H1W1···O4i1.032.003.028 (2)174
O7—H7O···O1ii0.94 (2)1.85 (2)2.7818 (14)171.7 (18)
O3—H3O···O5ii0.942 (19)1.942 (19)2.8796 (14)173.2 (17)
O2—H2O···O6ii1.23 (2)1.23 (2)2.4395 (13)164 (2)
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O81.001.942.898 (2)159.5
O1W—H1W1···O4i1.032.003.028 (2)173.5
O7—H7O···O1ii0.94 (2)1.85 (2)2.7818 (14)171.7 (18)
O3—H3O···O5ii0.942 (19)1.942 (19)2.8796 (14)173.2 (17)
O2—H2O···O6ii1.23 (2)1.23 (2)2.4395 (13)164 (2)
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula2C10H16N+·2C24H13O8−·1.5H2O
Mr1186.19
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)10.934 (2), 11.088 (2), 12.402 (2)
α, β, γ (°)102.873 (3), 106.083 (3), 95.548 (3)
V (Å3)1388.0 (4)
Z1
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.31 × 0.19 × 0.15
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.969, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections		15809, 5990, 4702
Rint0.068
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.108, 0.99
No. of reflections5990
No. of parameters414
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.26, −0.42

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This research was supported by the Pazy Research Foundation.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 399-402
doi:10.1107/S2056989016002899
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