3,6,9,16,19,22-Hexaaza­tricyclo­[22.2.2.211,14]­triaconta-1(27),11 (30),12,14(29),24(28),25-hexa­ene hexa­kis(p-toluene­sulfonate) dihydrate

Saeed, M.A.; Thompson, J.J.; Fronczek, F.R.; Hossain, M.A.

doi:10.1107/S1600536809035648

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2405-o2406

doi:10.1107/S1600536809035648

Open

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3,6,9,16,19,22-Hexaazatricyclo[22.2.2.2^11,14]triaconta-1(27),11 (30),12,14(29),24(28),25-hexaene hexakis(p-toluenesulfonate) dihydrate

Musabbir A. Saeed,^a Jameskia J. Thompson,^a Frank R. Fronczek ^b and Md. Alamgir Hossain ^a ^*

^aDepartment of Chemistry and Biochemistry, Jackson State University, MS 39217, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
^*Correspondence e-mail: alamgir@chem.jsums.edu

(Received 29 August 2009; accepted 3 September 2009; online 9 September 2009)

In the title compound, C₂₄H₄₄N₆⁶⁺·6C₇H₇O₃S⁻·2H₂O, the macrocycle crystallizes in its hexaprotonated form, accompanied by six p-toluenesulfonate ions and two water molecules, and lies on an inversion center. The three independent p-toluenesulfonate anions and their inversion equivalents at (1 − x, 1 − y, 1 − z) are linked to the macrocyclic cation through N—H⋯O hydrogen bonds. Of these, two p-toluenesulfonate ions are located on opposite sides of the macrocyclic plane and are linked to bridgehead N atoms via N—H⋯O hydrogen bonds. The remaining four p-toluenesulfonate ions bridge two adjacent macrocyclic cationic units through N—H⋯O hydrogen bonding involving other N atoms, forming a chain along the a axis. The water molecules, which could not be located and may be disordered, do not interact with the macrocycle; however, they form hydrogen bonds with anions.

Related literature

For general background, see: Bianchi et al. (1997 ); Chen & Martell (1991 ); Hossain (2008 ); Llobet et al. (1994 ); Nagarajan & Ganem (1987 ); Ragunathan & Schneider (1996 ). For related structures, see: Bazzicalupi et al. (1995 ); Clifford et al. (2001 ); He et al. (2000 ); Li et al. (2009 ); Liu et al. (2008 ); Lu et al. (1995 , 1998 ); Zhu et al. (2002 ).

Experimental

Crystal data

C₂₄H₄₄N₆⁶⁺·6C₇H₇O₃S⁻·2H₂O
M_r = 1479.80
Triclinic, $[P \overline 1]$
a = 11.513 (3) Å
b = 12.639 (5) Å
c = 13.556 (6) Å
α = 78.578 (16)°
β = 71.88 (2)°
γ = 89.30 (2)°
V = 1835.0 (12) Å³
Z = 1
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 90 K
0.17 × 0.10 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.947, T_max = 0.992
27691 measured reflections
7213 independent reflections
2920 reflections with I > 2σ(I)
R_int = 0.145

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.156
S = 0.97
7213 reflections
446 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11N⋯O7ⁱ	0.92	1.86	2.738 (5)	159
N1—H12N⋯O8	0.92	2.10	2.923 (6)	148
N1—H12N⋯O9	0.92	2.33	3.130 (5)	145
N2—H21N⋯O5	0.92	1.85	2.745 (5)	164
N2—H22N⋯O1ⁱⁱ	0.92	1.83	2.706 (4)	159
N3—H31N⋯O4ⁱⁱ	0.92	1.84	2.748 (4)	168
N3—H32N⋯O2	0.92	1.92	2.842 (5)	177
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035648/ci2898sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035648/ci2898Isup2.hkl

checkCIF report

Comment top

Azamacrocyles mimic many natural polyamines including putrescine, spermidine and spermine, that are known to complex negatively charged nucleotides through hydrogen bonding interactions with phosphate groups (Nagarajan & Ganem, 1987; Bianchi et al., 1997)). Simple hexaazamacrocycles which are conveniently synthesized from Schiff base derived reaction (Chen & Martell, 1991) are known to complex both anions and cations (Llobet et al., 1994; Hossain, 2008). For example, m-xylyl macrocycle with six N atoms and rigid spacers were shown to form complexes with sulfate (Clifford et al., 2001), pyrophosphate (Lu et al., 1995), and triphosphate (Lu et al., 1998). A m-xylyl analogue with propylene chains, was recently reported to complex with chloride showing a chair-like structure, where chloride anions are bonded to protonated amines outside the cavity (Liu et al., 2008). The macrocycle in the title compound containing slightly larger cavity with p-xylyl groups, was reported to bind perchlorate (Bazzicalupi, et al., 1995) and benzene-1,2,4,5-tetracarboxylate ((Zhu et al., 2002) in the tetraprotonated form. Incorporating metal ions, this compound was found to catalyze the hydrolysis of bis(p-nitrophenyl)-phosphate (Ragunathan & Schneider, 1996), and was also shown to bind calf thymus DNA (Li et al., 2009). As a part of our work in the field of anion recognition, we synthesized the p-xylyl based macrocycle and isolated crystals of the p-toluenesulfonate salt. This report describes the synthesis and structural aspect of a ditopic anion complex of p-xylyl macrocycle.

Single crystal analysis of the p-toluenesulfonate salt reveals that the ligand is hexaprotonated and crystallized with six p-toluenesulfonate anions and two water molecules. Each protonated amine of the macrocycle is involved in coordinating one p-toluenesulfonate with short (N···O) hydrogen bonds (Table 1). The cationic macrocycle lies on an inversion center. The macrocycle is found to adopt a rectangular shape in which two aromatic units are parallel to each other with a centroid-to-centroid distance of 9.990 Å (Fig. 1). The shape of the macrocycle is quite different from those observed in the neutral macrocycle (He et al., 2000) or its larger cationic analogue with m-xylyl spacers in the chloride complex (Liu et al., 2008), both of which adopt a chair conformation with two flip-flop aromatic moieties. In the solid state, the hydrogen atoms on the bridgehead amines direct toward the cavity, while those on the remaining nitrogen atoms point outwards from the cavity to minimize the electrostatic repulsion forces. The NCCN chains (N1—C1—C2—N2, N3—C11—C12—N1 and their symmetry related counterparts) linking the bridgehead N atoms, are essentially unstrained, with the torsion angles of -172.0 (4) and 170.9 (4)°, close to the trans conformation (ca 180°). On the other hand, gauche conformations (ca 60°) were found for the CNCC chains (C2—N2—C3—C4, C11—N3—C10—C7ⁱ and their counterparts) associated with the aromatic rings, with torsion angles of -51.8 (5) and 51.9 (5)°.

All six p-toluenesulfonate anions are strongly bonded to both faces of the macrocycle, with three groups at each face (Fig. 2). Four p-toluenesulfonates are singly bonded to the protonated amines (N2, N2ⁱ, N3 and N3ⁱ) linking the aromatic spacers, with almost linear N—H···O interactions (164 to 177 °). The distances in N···O bonds are in the range from 2.706 (4) to 2.842 (5) Å. Two other anionic groups are located above and below the macrocyclic plane, each with two N···O bonds with the central amines (N1 and N1ⁱ). In this case two oxygen atoms, O7 and O8 and their symmetry related O7ⁱⁱ and O8ⁱⁱ act as hydrogen bond acceptors and bridge the amines from the opposite sides. These two anions are partially included in the cavity with a ditopic binding mode (Fig. 3). In the crystal structure, the ionic units are linked by N—H..O hydrogen bonds forming a chain along the a axis. Along the c axis, the C4-C9 aromatic rings of the adjacent chains are stacked, with a centroid-to-centroid distance of 4.533 (3) Å (Fig. 4). The anions are found within the channels formed by the macrocycles, facing in opposite directions alternatively and are linked to the macrocycles with extensive hydrogen bonding frameworks.

In summary, a novel ditopic complex of p-toluenesulfonate anion has been synthesized, and its structure has been presented. The surrounding p-toluenesulfonates act as hydrogen bond acceptors for the nitrogen sites in the macrocycle, and play an important role in forming a hydrogen bonding network in the three dimensional structure. The water molecules do not interact with the macrocycle, however they form hydrogen bonds with anions.

Related literature top

For general background, see: Bianchi et al. (1997); Hossain (2008). For related literature, see: Bazzicalupi et al. (1995); Chen & Martell (1991); Clifford et al. (2001); He et al. (2000); Li et al. (2009); Liu et al. (2008); Llobet et al. (1994); Lu et al. (1995, 1998); Nagarajan & Ganem (1987); Ragunathan & Schneider (1996); Zhu et al. (2002). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see&ctdot;" it said, for example, "For general background, see&ctdot;. For related structures, see···; etc. Please revise this section as indicated.

Experimental top

The synthesis was carried out following a modified literature procedure (Chen & Martell, 1991). An equimolar amount of diethylenetriamine (1.00 g, 9.70 x 10 ^-3 mol) in CH₃OH (200 ml) and terephthalaldehyde (1.30 g, 9.70 x 10 ^-3 mol) in CH₃OH (200 ml) were added to CH₃OH (400 ml) over 4 h at 0°C. The mixture was stirred at room temperature for another 24 h. After the solvent was evaporated, the Schiff base was reduced to amine with NaBH₄ (1.73 g, 45.7 x 10 ^-3 mol) in CH₃OH (100 ml) at room temperature for 12 h. After evaporating the solvent under reduced pressure, the residue was dissolved in 1 M aq NaOH solution (100 ml), and the aqueous phase was extracted by CH₂Cl₂ (3x100 ml). The organic layers were combined and dried with MgSO₄. Evaporation of the solvent gave a white powder of the neutral macrocycle. Yield: 60%. ¹H NMR (300 MHz, CDCl₃, TMS): δ 7.29 (s, 8H, ArH), 3.80 (s, 8H, ArCH₂), 2.85 (t, 8H, CH₂), 2.83 (t, 8H, CH₂). The p-toluenesulfonate salt was obtained by titrating the macrocycle (50 mg) dissolved in CH₃OH (2 ml) with TsOH. The addition of diethyl ether (2 ml) yielded a white precipitate of p-toluenesulfonate salt that was filtered and dried. Yield: 80%. ¹H NMR (300 MHz, D₂O, TSP): δ 7.70 (d, 12H, ArH), 7.42 (d, 12H, ArH), 7.26 (s, 8H, ArH), 4.21 (s, 8H, ArCH₂), 3.27 (t, 8H, CH₂), 3.01 (t, 8H, CH₂), 2.43 (s, 12H, CH₂). Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of cationic unit in (1). Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z].
	Fig. 2. The molecular structure of (1) showing the atom-numbering scheme and hydrogen bonding interactions. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 2 - x, 1 - y, 1 - z.]
	Fig. 3. Space-filling view of (1) showing two anions bonded with macrocycle at the both faces.
	Fig. 4. View of a hydrogen-bonded (dashed lines) chain in (1).

3,6,9,16,19,22-Hexaazatricyclo[22.2.2.2^11,14]triaconta- 1(27),11 (30),12,14 (29),24 (28),25-hexaene hexakis(p-toluenesulfonate) dihydrate top

Crystal data top

C₂₄H₄₄N₆⁶⁺·6C₇H₇O₃S⁻·2H₂O	Z = 1
M_r = 1479.80	F(000) = 784
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.513 (3) Å	Cell parameters from 6760 reflections
b = 12.639 (5) Å	θ = 2.5–26.0°
c = 13.556 (6) Å	µ = 0.26 mm⁻¹
α = 78.578 (16)°	T = 90 K
β = 71.88 (2)°	Plate, colorless
γ = 89.30 (2)°	0.17 × 0.10 × 0.03 mm
V = 1835.0 (12) Å³

Data collection top

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	7213 independent reflections
Radiation source: fine-focus sealed tube	2920 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.145
ω and ϕ scans	θ_max = 26.3°, θ_min = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −13→14
T_min = 0.947, T_max = 0.992	k = −15→15
27691 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.072	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0515P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
7213 reflections	Δρ_max = 0.39 e Å⁻³
446 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (7)

Crystal data top

C₂₄H₄₄N₆⁶⁺·6C₇H₇O₃S⁻·2H₂O	γ = 89.30 (2)°
M_r = 1479.80	V = 1835.0 (12) Å³
Triclinic, P1	Z = 1
a = 11.513 (3) Å	Mo Kα radiation
b = 12.639 (5) Å	µ = 0.26 mm⁻¹
c = 13.556 (6) Å	T = 90 K
α = 78.578 (16)°	0.17 × 0.10 × 0.03 mm
β = 71.88 (2)°

Data collection top

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	7213 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2920 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.992	R_int = 0.145
27691 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 0.97	Δρ_max = 0.39 e Å⁻³
7213 reflections	Δρ_min = −0.33 e Å⁻³
446 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.7392 (3)	0.5311 (3)	0.4777 (3)	0.0292 (10)
H11N	0.7039	0.5968	0.4705	0.035*
H12N	0.6798	0.4779	0.4892	0.035*
N2	0.8843 (3)	0.5451 (3)	0.1864 (3)	0.0242 (10)
H21N	0.8920	0.4720	0.1907	0.029*
H22N	0.9589	0.5751	0.1815	0.029*
N3	0.7276 (3)	0.5161 (3)	0.7591 (3)	0.0222 (9)
H31N	0.8044	0.5469	0.7455	0.027*
H32N	0.7331	0.4423	0.7725	0.027*
C1	0.8391 (4)	0.5271 (4)	0.3779 (3)	0.0331 (13)
H1A	0.8667	0.4525	0.3792	0.040*
H1B	0.9097	0.5751	0.3710	0.040*
C2	0.7921 (4)	0.5632 (4)	0.2853 (3)	0.0263 (12)
H2A	0.7146	0.5220	0.2974	0.032*
H2B	0.7753	0.6409	0.2782	0.032*
C3	0.8538 (4)	0.5918 (4)	0.0876 (4)	0.0281 (12)
H3A	0.8608	0.6717	0.0750	0.034*
H3B	0.9132	0.5688	0.0264	0.034*
C4	0.7271 (4)	0.5565 (4)	0.0956 (3)	0.0219 (11)
C5	0.6934 (4)	0.4486 (4)	0.1162 (3)	0.0276 (12)
H5	0.7526	0.3962	0.1200	0.033*
C6	0.5747 (4)	0.4155 (4)	0.1315 (4)	0.0286 (12)
H6	0.5525	0.3404	0.1469	0.034*
C7	0.4869 (4)	0.4901 (4)	0.1246 (3)	0.0245 (12)
C8	0.5205 (4)	0.5989 (4)	0.1009 (3)	0.0253 (12)
H8	0.4624	0.6513	0.0933	0.030*
C9	0.6402 (4)	0.6312 (4)	0.0885 (3)	0.0247 (12)
H9	0.6625	0.7060	0.0748	0.030*
C10	0.6439 (3)	0.5474 (4)	0.8560 (3)	0.0239 (12)
H10A	0.6493	0.6270	0.8477	0.029*
H10B	0.6698	0.5149	0.9180	0.029*
C11	0.6896 (4)	0.5483 (4)	0.6635 (3)	0.0246 (12)
H11A	0.6815	0.6275	0.6486	0.030*
H11B	0.6092	0.5124	0.6751	0.030*
C12	0.7840 (4)	0.5161 (5)	0.5708 (4)	0.0389 (15)
H12A	0.8608	0.5607	0.5523	0.047*
H12B	0.8019	0.4394	0.5905	0.047*
S1	0.86065 (10)	0.27995 (10)	0.83408 (10)	0.0307 (4)
O1	0.8820 (2)	0.3732 (2)	0.8763 (3)	0.0301 (9)
O2	0.7479 (2)	0.2887 (2)	0.8063 (2)	0.0321 (9)
O3	0.9661 (3)	0.2628 (3)	0.7468 (3)	0.0405 (10)
C13	0.8414 (4)	0.1649 (4)	0.9368 (4)	0.0239 (12)
C14	0.8237 (4)	0.0639 (4)	0.9169 (4)	0.0368 (14)
H14	0.8200	0.0575	0.8493	0.044*
C15	0.8115 (4)	−0.0272 (4)	0.9950 (4)	0.0385 (14)
H15	0.7995	−0.0961	0.9805	0.046*
C16	0.8164 (4)	−0.0201 (4)	1.0952 (4)	0.0298 (13)
C17	0.8351 (4)	0.0810 (4)	1.1128 (4)	0.0349 (13)
H17	0.8388	0.0876	1.1803	0.042*
C18	0.8485 (4)	0.1730 (4)	1.0349 (4)	0.0370 (14)
H18	0.8625	0.2417	1.0488	0.044*
C19	0.8042 (4)	−0.1200 (4)	1.1794 (4)	0.0389 (14)
H19A	0.8052	−0.0996	1.2452	0.058*
H19B	0.8725	−0.1659	1.1561	0.058*
H19C	0.7267	−0.1599	1.1919	0.058*
S2	1.03881 (10)	0.29487 (10)	0.21857 (10)	0.0261 (4)
O4	1.0570 (2)	0.3649 (2)	0.2876 (2)	0.0265 (8)
O5	0.9472 (2)	0.3379 (2)	0.1689 (2)	0.0310 (9)
O6	1.1516 (2)	0.2716 (2)	0.1447 (2)	0.0318 (9)
C20	0.9732 (4)	0.1722 (4)	0.3034 (4)	0.0243 (12)
C21	1.0362 (4)	0.0795 (4)	0.3002 (4)	0.0413 (14)
H21	1.1164	0.0814	0.2517	0.050*
C22	0.9831 (5)	−0.0177 (4)	0.3677 (5)	0.0515 (16)
H22	1.0270	−0.0817	0.3641	0.062*
C23	0.8652 (5)	−0.0217 (5)	0.4410 (4)	0.0444 (15)
C24	0.8042 (4)	0.0714 (5)	0.4437 (4)	0.0429 (15)
H24	0.7245	0.0699	0.4930	0.052*
C25	0.8559 (4)	0.1684 (4)	0.3760 (4)	0.0344 (13)
H25	0.8113	0.2321	0.3791	0.041*
C26	0.8091 (5)	−0.1286 (4)	0.5137 (5)	0.0640 (19)
H26A	0.7470	−0.1148	0.5774	0.096*
H26B	0.8731	−0.1706	0.5340	0.096*
H26C	0.7709	−0.1694	0.4765	0.096*
S3	0.51388 (11)	0.31199 (11)	0.53979 (12)	0.0374 (4)
O7	0.4106 (3)	0.2991 (3)	0.5021 (3)	0.0422 (10)
O8	0.6303 (3)	0.3321 (3)	0.4573 (3)	0.0696 (14)
O9	0.4946 (3)	0.3943 (3)	0.6041 (3)	0.0540 (11)
C27	0.5184 (4)	0.1876 (4)	0.6248 (4)	0.0338 (13)
C28	0.4736 (4)	0.0918 (4)	0.6118 (5)	0.0427 (15)
H28	0.4402	0.0912	0.5560	0.051*
C29	0.4784 (5)	−0.0029 (5)	0.6816 (6)	0.061 (2)
H29	0.4467	−0.0685	0.6733	0.073*
C30	0.5274 (5)	−0.0056 (5)	0.7628 (6)	0.070 (2)
C31	0.5708 (5)	0.0922 (5)	0.7738 (5)	0.075 (2)
H31	0.6030	0.0934	0.8302	0.089*
C32	0.5681 (4)	0.1871 (5)	0.7050 (5)	0.0520 (17)
H32	0.6006	0.2526	0.7127	0.062*
C33	0.5288 (6)	−0.1102 (5)	0.8403 (7)	0.118 (4)
H33A	0.5662	−0.1657	0.8009	0.177*
H33B	0.4448	−0.1346	0.8840	0.177*
H33C	0.5764	−0.0978	0.8860	0.177*
O10	1.0391 (4)	0.6764 (4)	0.4660 (4)	0.0990 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.024 (2)	0.042 (3)	0.019 (2)	0.0028 (19)	−0.0035 (19)	−0.009 (2)
N2	0.0124 (19)	0.037 (3)	0.022 (2)	0.0006 (17)	−0.0023 (17)	−0.007 (2)
N3	0.0195 (19)	0.028 (2)	0.018 (2)	−0.0020 (17)	−0.0027 (17)	−0.0059 (19)
C1	0.023 (3)	0.056 (4)	0.021 (3)	0.007 (2)	−0.005 (2)	−0.013 (3)
C2	0.021 (2)	0.033 (3)	0.024 (3)	0.000 (2)	−0.003 (2)	−0.011 (3)
C3	0.018 (2)	0.048 (3)	0.018 (3)	−0.001 (2)	−0.005 (2)	−0.006 (3)
C4	0.014 (2)	0.036 (3)	0.015 (3)	0.001 (2)	−0.001 (2)	−0.011 (2)
C5	0.019 (3)	0.039 (4)	0.027 (3)	0.006 (2)	−0.006 (2)	−0.013 (3)
C6	0.028 (3)	0.027 (3)	0.031 (3)	−0.007 (2)	−0.009 (2)	−0.005 (3)
C7	0.020 (3)	0.035 (3)	0.022 (3)	0.004 (2)	−0.008 (2)	−0.010 (3)
C8	0.021 (3)	0.034 (3)	0.021 (3)	0.005 (2)	−0.006 (2)	−0.007 (2)
C9	0.022 (3)	0.030 (3)	0.019 (3)	−0.007 (2)	0.000 (2)	−0.006 (2)
C10	0.021 (3)	0.034 (3)	0.016 (3)	0.000 (2)	−0.004 (2)	−0.006 (2)
C11	0.023 (2)	0.033 (3)	0.022 (3)	0.002 (2)	−0.013 (2)	−0.005 (2)
C12	0.025 (3)	0.075 (4)	0.015 (3)	0.009 (3)	−0.005 (2)	−0.010 (3)
S1	0.0238 (7)	0.0303 (9)	0.0379 (9)	0.0036 (6)	−0.0102 (6)	−0.0060 (7)
O1	0.0245 (17)	0.022 (2)	0.047 (2)	−0.0024 (14)	−0.0159 (16)	−0.0081 (17)
O2	0.0287 (18)	0.029 (2)	0.042 (2)	0.0011 (15)	−0.0177 (16)	−0.0050 (17)
O3	0.0298 (19)	0.044 (2)	0.038 (2)	0.0123 (16)	−0.0013 (17)	−0.0027 (18)
C13	0.016 (2)	0.024 (3)	0.033 (3)	0.004 (2)	−0.006 (2)	−0.009 (3)
C14	0.052 (3)	0.033 (4)	0.035 (4)	−0.003 (3)	−0.020 (3)	−0.017 (3)
C15	0.047 (3)	0.026 (4)	0.044 (4)	0.000 (3)	−0.014 (3)	−0.013 (3)
C16	0.025 (3)	0.028 (4)	0.036 (4)	0.003 (2)	−0.010 (2)	−0.007 (3)
C17	0.045 (3)	0.029 (4)	0.030 (3)	0.002 (3)	−0.014 (3)	−0.003 (3)
C18	0.036 (3)	0.032 (4)	0.052 (4)	−0.003 (2)	−0.018 (3)	−0.022 (3)
C19	0.039 (3)	0.039 (4)	0.039 (4)	0.002 (3)	−0.012 (3)	−0.006 (3)
S2	0.0209 (7)	0.0306 (8)	0.0250 (8)	−0.0015 (6)	−0.0034 (6)	−0.0079 (7)
O4	0.0207 (16)	0.031 (2)	0.030 (2)	−0.0027 (14)	−0.0065 (14)	−0.0141 (17)
O5	0.0295 (18)	0.035 (2)	0.034 (2)	0.0029 (15)	−0.0168 (16)	−0.0073 (17)
O6	0.0240 (17)	0.039 (2)	0.024 (2)	0.0006 (15)	0.0047 (15)	−0.0082 (17)
C20	0.024 (3)	0.027 (3)	0.026 (3)	0.001 (2)	−0.011 (2)	−0.010 (2)
C21	0.031 (3)	0.035 (4)	0.049 (4)	−0.001 (3)	0.001 (3)	−0.011 (3)
C22	0.056 (4)	0.025 (4)	0.068 (5)	0.004 (3)	−0.017 (3)	−0.001 (3)
C23	0.039 (3)	0.041 (4)	0.052 (4)	−0.016 (3)	−0.021 (3)	0.006 (3)
C24	0.031 (3)	0.047 (4)	0.043 (4)	−0.011 (3)	−0.008 (3)	0.002 (3)
C25	0.024 (3)	0.035 (4)	0.041 (4)	0.002 (2)	−0.009 (3)	−0.004 (3)
C26	0.061 (4)	0.046 (4)	0.080 (5)	−0.022 (3)	−0.030 (3)	0.014 (4)
S3	0.0244 (7)	0.0398 (10)	0.0454 (10)	0.0028 (6)	−0.0109 (7)	−0.0034 (8)
O7	0.040 (2)	0.046 (2)	0.051 (3)	0.0073 (17)	−0.0270 (18)	−0.0139 (19)
O8	0.032 (2)	0.066 (3)	0.075 (3)	0.0132 (19)	0.012 (2)	0.021 (2)
O9	0.075 (3)	0.033 (2)	0.072 (3)	0.0047 (19)	−0.045 (2)	−0.017 (2)
C27	0.022 (3)	0.035 (4)	0.046 (4)	−0.002 (2)	−0.014 (3)	−0.008 (3)
C28	0.031 (3)	0.033 (4)	0.063 (4)	−0.009 (3)	−0.010 (3)	−0.016 (3)
C29	0.039 (3)	0.021 (4)	0.114 (6)	−0.004 (3)	−0.014 (4)	−0.008 (4)
C30	0.051 (4)	0.036 (4)	0.120 (6)	−0.011 (3)	−0.047 (4)	0.023 (4)
C31	0.071 (5)	0.057 (5)	0.102 (6)	−0.025 (4)	−0.059 (4)	0.022 (4)
C32	0.052 (4)	0.034 (4)	0.070 (5)	−0.018 (3)	−0.032 (3)	0.012 (3)
C33	0.106 (6)	0.049 (5)	0.193 (9)	−0.030 (4)	−0.087 (6)	0.058 (6)
O10	0.116 (4)	0.111 (4)	0.087 (4)	0.044 (3)	−0.047 (3)	−0.039 (3)

Geometric parameters (Å, º) top

N1—C12	1.484 (5)	C15—C16	1.397 (7)
N1—C1	1.488 (5)	C15—H15	0.95
N1—H11N	0.92	C16—C17	1.376 (6)
N1—H12N	0.92	C16—C19	1.501 (6)
N2—C2	1.486 (5)	C17—C18	1.381 (6)
N2—C3	1.496 (5)	C17—H17	0.95
N2—H21N	0.92	C18—H18	0.95
N2—H22N	0.92	C19—H19A	0.98
N3—C11	1.476 (5)	C19—H19B	0.98
N3—C10	1.490 (5)	C19—H19C	0.98
N3—H31N	0.92	S2—O6	1.440 (3)
N3—H32N	0.92	S2—O5	1.465 (3)
C1—C2	1.506 (6)	S2—O4	1.469 (3)
C1—H1A	0.99	S2—C20	1.754 (5)
C1—H1B	0.99	C20—C21	1.372 (6)
C2—H2A	0.99	C20—C25	1.397 (6)
C2—H2B	0.99	C21—C22	1.394 (7)
C3—C4	1.496 (5)	C21—H21	0.95
C3—H3A	0.99	C22—C23	1.406 (7)
C3—H3B	0.99	C22—H22	0.95
C4—C5	1.372 (6)	C23—C24	1.363 (7)
C4—C9	1.379 (6)	C23—C26	1.521 (7)
C5—C6	1.374 (5)	C24—C25	1.390 (6)
C5—H5	0.95	C24—H24	0.95
C6—C7	1.386 (6)	C25—H25	0.95
C6—H6	0.95	C26—H26A	0.98
C7—C8	1.380 (6)	C26—H26B	0.98
C7—C10ⁱ	1.511 (5)	C26—H26C	0.98
C8—C9	1.391 (5)	S3—O8	1.440 (4)
C8—H8	0.95	S3—O7	1.455 (3)
C9—H9	0.95	S3—O9	1.457 (4)
C10—C7ⁱ	1.511 (5)	S3—C27	1.766 (5)
C10—H10A	0.99	C27—C32	1.375 (7)
C10—H10B	0.99	C27—C28	1.386 (6)
C11—C12	1.506 (6)	C28—C29	1.383 (7)
C11—H11A	0.99	C28—H28	0.95
C11—H11B	0.99	C29—C30	1.380 (8)
C12—H12A	0.99	C29—H29	0.95
C12—H12B	0.99	C30—C31	1.391 (8)
S1—O2	1.457 (3)	C30—C33	1.521 (8)
S1—O3	1.457 (3)	C31—C32	1.373 (7)
S1—O1	1.463 (3)	C31—H31	0.95
S1—C13	1.765 (5)	C32—H32	0.95
C13—C18	1.381 (6)	C33—H33A	0.98
C13—C14	1.386 (6)	C33—H33B	0.98
C14—C15	1.376 (6)	C33—H33C	0.98
C14—H14	0.95

C12—N1—C1	112.2 (3)	C15—C14—C13	120.1 (5)
C12—N1—H11N	109.2	C15—C14—H14	119.9
C1—N1—H11N	109.2	C13—C14—H14	119.9
C12—N1—H12N	109.2	C14—C15—C16	121.1 (5)
C1—N1—H12N	109.2	C14—C15—H15	119.4
H11N—N1—H12N	107.9	C16—C15—H15	119.4
C2—N2—C3	113.9 (3)	C17—C16—C15	117.7 (5)
C2—N2—H21N	108.8	C17—C16—C19	121.6 (5)
C3—N2—H21N	108.8	C15—C16—C19	120.7 (5)
C2—N2—H22N	108.8	C16—C17—C18	121.8 (5)
C3—N2—H22N	108.8	C16—C17—H17	119.1
H21N—N2—H22N	107.7	C18—C17—H17	119.1
C11—N3—C10	114.6 (3)	C17—C18—C13	119.9 (5)
C11—N3—H31N	108.6	C17—C18—H18	120.1
C10—N3—H31N	108.6	C13—C18—H18	120.1
C11—N3—H32N	108.6	C16—C19—H19A	109.5
C10—N3—H32N	108.6	C16—C19—H19B	109.5
H31N—N3—H32N	107.6	H19A—C19—H19B	109.5
N1—C1—C2	109.0 (3)	C16—C19—H19C	109.5
N1—C1—H1A	109.9	H19A—C19—H19C	109.5
C2—C1—H1A	109.9	H19B—C19—H19C	109.5
N1—C1—H1B	109.9	O6—S2—O5	113.90 (19)
C2—C1—H1B	109.9	O6—S2—O4	113.11 (17)
H1A—C1—H1B	108.3	O5—S2—O4	110.35 (19)
N2—C2—C1	109.8 (3)	O6—S2—C20	107.5 (2)
N2—C2—H2A	109.7	O5—S2—C20	105.69 (19)
C1—C2—H2A	109.7	O4—S2—C20	105.7 (2)
N2—C2—H2B	109.7	C21—C20—C25	119.2 (4)
C1—C2—H2B	109.7	C21—C20—S2	120.8 (4)
H2A—C2—H2B	108.2	C25—C20—S2	120.0 (4)
C4—C3—N2	111.6 (3)	C20—C21—C22	120.4 (5)
C4—C3—H3A	109.3	C20—C21—H21	119.8
N2—C3—H3A	109.3	C22—C21—H21	119.8
C4—C3—H3B	109.3	C21—C22—C23	120.5 (5)
N2—C3—H3B	109.3	C21—C22—H22	119.7
H3A—C3—H3B	108.0	C23—C22—H22	119.7
C5—C4—C9	118.8 (4)	C24—C23—C22	118.4 (5)
C5—C4—C3	120.4 (4)	C24—C23—C26	122.0 (5)
C9—C4—C3	120.7 (4)	C22—C23—C26	119.6 (5)
C4—C5—C6	120.6 (4)	C23—C24—C25	121.5 (5)
C4—C5—H5	119.7	C23—C24—H24	119.2
C6—C5—H5	119.7	C25—C24—H24	119.2
C5—C6—C7	120.9 (4)	C24—C25—C20	120.0 (5)
C5—C6—H6	119.6	C24—C25—H25	120.0
C7—C6—H6	119.6	C20—C25—H25	120.0
C8—C7—C6	119.0 (4)	C23—C26—H26A	109.5
C8—C7—C10ⁱ	120.6 (4)	C23—C26—H26B	109.5
C6—C7—C10ⁱ	120.3 (4)	H26A—C26—H26B	109.5
C7—C8—C9	119.4 (4)	C23—C26—H26C	109.5
C7—C8—H8	120.3	H26A—C26—H26C	109.5
C9—C8—H8	120.3	H26B—C26—H26C	109.5
C4—C9—C8	121.2 (4)	O8—S3—O7	114.2 (2)
C4—C9—H9	119.4	O8—S3—O9	110.6 (2)
C8—C9—H9	119.4	O7—S3—O9	111.7 (2)
N3—C10—C7ⁱ	111.1 (4)	O8—S3—C27	107.7 (2)
N3—C10—H10A	109.4	O7—S3—C27	105.5 (2)
C7ⁱ—C10—H10A	109.4	O9—S3—C27	106.6 (2)
N3—C10—H10B	109.4	C32—C27—C28	120.0 (5)
C7ⁱ—C10—H10B	109.4	C32—C27—S3	118.6 (4)
H10A—C10—H10B	108.0	C28—C27—S3	121.3 (4)
N3—C11—C12	109.2 (3)	C29—C28—C27	118.7 (5)
N3—C11—H11A	109.8	C29—C28—H28	120.7
C12—C11—H11A	109.8	C27—C28—H28	120.7
N3—C11—H11B	109.8	C30—C29—C28	122.4 (5)
C12—C11—H11B	109.8	C30—C29—H29	118.8
H11A—C11—H11B	108.3	C28—C29—H29	118.8
N1—C12—C11	110.5 (4)	C29—C30—C31	117.3 (5)
N1—C12—H12A	109.6	C29—C30—C33	121.5 (6)
C11—C12—H12A	109.6	C31—C30—C33	121.2 (6)
N1—C12—H12B	109.6	C32—C31—C30	121.4 (6)
C11—C12—H12B	109.6	C32—C31—H31	119.3
H12A—C12—H12B	108.1	C30—C31—H31	119.3
O2—S1—O3	112.8 (2)	C31—C32—C27	120.1 (5)
O2—S1—O1	110.85 (18)	C31—C32—H32	119.9
O3—S1—O1	111.88 (19)	C27—C32—H32	119.9
O2—S1—C13	107.44 (19)	C30—C33—H33A	109.5
O3—S1—C13	106.6 (2)	C30—C33—H33B	109.5
O1—S1—C13	106.9 (2)	H33A—C33—H33B	109.5
C18—C13—C14	119.4 (5)	C30—C33—H33C	109.5
C18—C13—S1	121.5 (4)	H33A—C33—H33C	109.5
C14—C13—S1	119.1 (4)	H33B—C33—H33C	109.5

C12—N1—C1—C2	−169.6 (4)	C14—C13—C18—C17	−1.5 (7)
C3—N2—C2—C1	−172.3 (4)	S1—C13—C18—C17	−178.9 (3)
N1—C1—C2—N2	−172.0 (4)	O6—S2—C20—C21	7.7 (4)
C2—N2—C3—C4	−51.8 (5)	O5—S2—C20—C21	129.6 (4)
N2—C3—C4—C5	−57.0 (6)	O4—S2—C20—C21	−113.4 (4)
N2—C3—C4—C9	119.2 (4)	O6—S2—C20—C25	−172.8 (4)
C9—C4—C5—C6	−1.2 (7)	O5—S2—C20—C25	−50.8 (4)
C3—C4—C5—C6	175.1 (4)	O4—S2—C20—C25	66.2 (4)
C4—C5—C6—C7	1.1 (7)	C25—C20—C21—C22	0.7 (8)
C5—C6—C7—C8	0.7 (7)	S2—C20—C21—C22	−179.7 (4)
C5—C6—C7—C10ⁱ	−178.6 (4)	C20—C21—C22—C23	−1.0 (8)
C6—C7—C8—C9	−2.4 (7)	C21—C22—C23—C24	0.5 (8)
C10ⁱ—C7—C8—C9	176.9 (4)	C21—C22—C23—C26	179.9 (5)
C5—C4—C9—C8	−0.5 (7)	C22—C23—C24—C25	0.2 (8)
C3—C4—C9—C8	−176.8 (4)	C26—C23—C24—C25	−179.2 (5)
C7—C8—C9—C4	2.3 (7)	C23—C24—C25—C20	−0.4 (8)
C11—N3—C10—C7ⁱ	51.9 (5)	C21—C20—C25—C24	−0.1 (7)
C10—N3—C11—C12	177.8 (4)	S2—C20—C25—C24	−179.6 (4)
C1—N1—C12—C11	165.6 (4)	O8—S3—C27—C32	84.8 (5)
N3—C11—C12—N1	170.9 (4)	O7—S3—C27—C32	−152.9 (4)
O2—S1—C13—C18	−119.5 (4)	O9—S3—C27—C32	−33.9 (5)
O3—S1—C13—C18	119.3 (4)	O8—S3—C27—C28	−95.0 (4)
O1—S1—C13—C18	−0.5 (4)	O7—S3—C27—C28	27.4 (5)
O2—S1—C13—C14	63.1 (4)	O9—S3—C27—C28	146.3 (4)
O3—S1—C13—C14	−58.1 (4)	C32—C27—C28—C29	1.0 (7)
O1—S1—C13—C14	−177.8 (3)	S3—C27—C28—C29	−179.3 (4)
C18—C13—C14—C15	1.0 (7)	C27—C28—C29—C30	−0.8 (8)
S1—C13—C14—C15	178.4 (3)	C28—C29—C30—C31	1.2 (9)
C13—C14—C15—C16	0.1 (7)	C28—C29—C30—C33	178.5 (6)
C14—C15—C16—C17	−0.6 (7)	C29—C30—C31—C32	−1.7 (10)
C14—C15—C16—C19	−179.4 (4)	C33—C30—C31—C32	−179.1 (6)
C15—C16—C17—C18	0.1 (7)	C30—C31—C32—C27	2.0 (9)
C19—C16—C17—C18	178.9 (4)	C28—C27—C32—C31	−1.5 (8)
C16—C17—C18—C13	1.0 (7)	S3—C27—C32—C31	178.7 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O7ⁱ	0.92	1.86	2.738 (5)	159
N1—H12N···O8	0.92	2.10	2.923 (6)	148
N1—H12N···O9	0.92	2.33	3.130 (5)	145
N2—H21N···O5	0.92	1.85	2.745 (5)	164
N2—H22N···O1ⁱⁱ	0.92	1.83	2.706 (4)	159
N3—H31N···O4ⁱⁱ	0.92	1.84	2.748 (4)	168
N3—H32N···O2	0.92	1.92	2.842 (5)	177
N3—H32N···O1	0.92	2.58	3.081 (4)	115

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₄₄N₆⁶⁺·6C₇H₇O₃S⁻·2H₂O
M_r	1479.80
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	11.513 (3), 12.639 (5), 13.556 (6)
α, β, γ (°)	78.578 (16), 71.88 (2), 89.30 (2)
V (Å³)	1835.0 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.17 × 0.10 × 0.03

Data collection
Diffractometer	Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.947, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	27691, 7213, 2920
R_int	0.145
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.156, 0.97
No. of reflections	7213
No. of parameters	446
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.33

Computer programs: COLLECT (Nonius, 1999), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O7ⁱ	0.92	1.86	2.738 (5)	159
N1—H12N···O8	0.92	2.10	2.923 (6)	148
N1—H12N···O9	0.92	2.33	3.130 (5)	145
N2—H21N···O5	0.92	1.85	2.745 (5)	164
N2—H22N···O1ⁱⁱ	0.92	1.83	2.706 (4)	159
N3—H31N···O4ⁱⁱ	0.92	1.84	2.748 (4)	168
N3—H32N···O2	0.92	1.92	2.842 (5)	177

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Acknowledgements

This work was supported by the National Institutes of Health, Division of National Center for Research Resources, under grant No. G12RR013459. The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

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Volume 65| Part 10| October 2009| Pages o2405-o2406

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,6,9,16,19,22-Hexa­aza­tri­cyclo­[22.2.2.211,14]­triaconta-1(27),11 (30),12,14(29),24(28),25-hexa­ene hexa­kis(p-toluene­sulfonate) dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,6,9,16,19,22-Hexaazatricyclo[22.2.2.2^11,14]triaconta-1(27),11 (30),12,14(29),24(28),25-hexaene hexakis(p-toluenesulfonate) dihydrate