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

Volume 65
Part 10
Pages o2405-o2406
October 2009

Received 29 August 2009
Accepted 3 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.008 Å
H completeness 96%
R = 0.072
wR = 0.156
Data-to-parameter ratio = 16.2
Details

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

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-HO 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-HO hydrogen bonds. The remaining four p-toluenesulfonate ions bridge two adjacent macrocyclic cationic units through N-HO 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
= 78.578 (16)°
= 71.88 (2)°
= 89.30 (2)°
V = 1835.0 (12) Å³
Z = 1
Mo K radiation
= 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 > 2(I)
R_int = 0.145

Refinement

R[F² > 2(F²)] = 0.072
wR(F²) = 0.156
S = 0.97
7213 reflections
446 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H11NO7ⁱ	0.92	1.86	2.738 (5)	159
N1-H12NO8	0.92	2.10	2.923 (6)	148
N1-H12NO9	0.92	2.33	3.130 (5)	145
N2-H21NO5	0.92	1.85	2.745 (5)	164
N2-H22NO1ⁱⁱ	0.92	1.83	2.706 (4)	159
N3-H31NO4ⁱⁱ	0.92	1.84	2.748 (4)	168
N3-H32NO2	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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2898 ).

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.

References

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