5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10,12,14-hexaen-1-ium chloride

Yichao Xu; Shouwen Jin; Jianlong Zhu; YingJia Liu; ChuanChuan Shi

doi:10.1107/S1600536811038189

. 2011 Sep 30;67(Pt 10):o2730. doi: 10.1107/S1600536811038189

5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadeca-2(7),3,5,10,12,14-hexaen-1-ium chloride

Yichao Xu ^a, Shouwen Jin ^a,^*, Jianlong Zhu ^a, YingJia Liu ^a, ChuanChuan Shi ^a

PMCID: PMC3201434 PMID: 22064997

Abstract

In the title salt, C₁₅H₁₇N₄O₄S₂ ⁺·Cl⁻, the chloride anion is disordered over two positions with occupancies of 0.776 (6) and 0.224 (6). The cation adopts an L shape and the dihedral angle between the benzene rings is 82.5 (3)°. In the crystal, inversion dimers of cations linked by pairs of N—H⋯N hydrogen bonds occur, with the bond arising from the protonated N atom. The cationic dimers are linked into chains via the disordered chloride ions by way of N—H⋯Cl hydrogen bonds and N—H⋯O, C—H⋯O and C—H⋯Cl interactions also occur, which help to consolidate the three-dimensional network.

Related literature

For a related structure and background references to supramolecular networks, see: Jin et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₇N₄O₄S₂ ⁺·Cl⁻
M _r = 416.90
Monoclinic,
a = 11.5247 (11) Å
b = 18.5693 (16) Å
c = 8.1489 (7) Å
β = 109.177 (1)°
V = 1647.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.40 × 0.33 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.815, T _max = 0.869
8082 measured reflections
2895 independent reflections
1944 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.219
S = 1.08
2895 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038189/hb6395sup1.cif

e-67-o2730-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038189/hb6395Isup2.hkl

e-67-o2730-Isup2.hkl^{(142.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038189/hb6395Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.89	2.26	3.081 (8)	153
N1—H1B⋯Cl1ⁱⁱ	0.89	2.26	3.141 (7)	170
N2—H2A⋯Cl1ⁱⁱⁱ	0.89	2.19	3.042 (6)	160
N2—H2B⋯O1^iv	0.89	2.46	3.109 (7)	130
N2—H2B⋯O2^iv	0.89	2.36	3.240 (7)	168
N4—H4⋯N2^v	0.91	2.02	2.922 (7)	173
C12—H12⋯O3^vi	0.93	2.49	3.416 (7)	175
C13—H13A⋯Cl1^vii	0.97	2.76	3.514 (7)	135
C14—H14A⋯O4ⁱ	0.97	2.50	3.212 (9)	130
C15—H15A⋯O3^viii	0.97	2.52	3.443 (7)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .

Acknowledgments

We gratefully acknowledge financial support by the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the innovation project of Zhejiang A & F University.

supplementary crystallographic information

Comment

Organic salts based on hydrogen bonding are a research field receiving great attention in recent years. As an extension of our study concentrating on hydrogen bonded assembly of organic acid and organic base (Jin et al., 2010), herein we report the crystal structure of 2,9-Dibenzenesulfonamide-1,5-diazaium-bicyclo[3.3.1]dimethanodibenzo chloride.

The crystal of the title compound of the formula C₁₅H₁₇ClN₄O₄S₂ was obtained by recrystallization of 2,9-Dibenzenesulfonamide-1,5-diazaium- bicyclo[3.3.1]dimethanodibenzo from methanol and HCl solution.

The compound is a salt. The asymmetric unit of the compound consists of one monocation, and one chloride anion (Fig. 1), respectively.

The chloride anion is disordered over two positions with occupancies of 0.78, and 0.22 respectively. In the compound there is a mirror plane running through the C15 atom. Two cations formed dimers via the N—H···N hydrogen bond between the NH₊ cation and the amino group with N—N separation of 2.922 (6) A%. The cation dimers were connected together via the chloride anion through CH—Cl, Cl—O, and N—H···Cl contacts to form one-dimensional chain (A) running along the b axis direction (Fig. 2). Such adjacent chains were combined together by the CH₂—O, and CH—O interactions to form two-dimensional sheet extending along the bc plane. Such kind of sheets were stacked along the a axis direction via the CH2—Cl interactions to form three-dimensional network structure. It is worthy to note that there are one-dimensional chains (B) that are running through the three-dimensional network. And such kind of chains were connected with the three-dimensional network through the N—H···S, and N—H···O interactions.

Experimental

A solution of 2,9-dibenzenesulfonamide-1,5-diazabicyclo[3.3.1]dimethanodibenzo (38 mg, 0.1 mmol) was dissolved in 5 ml of methanol and 1 ml of conc. HCl under continuous stirring. The solution was stirred for about 1 h at room temperature, then the solution was filtered into a test tube. The solution was left standing at room temperature for several days, colorless block crystals were isolated after slow evaporation of the solution in air at ambient temperature. The crystals were collected and dried in air to give the title compound.