(IUCr) 4-Amino-2-methylquinolinium hydrogensulfate dihydrate

Volume 64
Part 1
Page o203
January 2008

Received 19 November 2007
Accepted 28 November 2007
Online 6 December 2007

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.060
wR = 0.182
Data-to-parameter ratio = 17.1
Details

4-Amino-2-methylquinolinium hydrogensulfate dihydrate

Mostafa M. Amini,^a ^* Gholamhossein Mohammadnezhad Sh.^a and Hamid Reza Khavasi ^a

^aDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran
Correspondence e-mail: m-pouramini@cc.sbu.ac.ir

In the title compound, C₁₀H₁₁N₂⁺·HSO₄^-·2H₂O, the asymmetric unit contains two protonated 4-aminoquinoline cations and two hydrogen sulfate anions with four water molecules. The crystal structure involves extensive N-HO and O-HO hydrogen bonding.

Related literature

For related literature, see: Amini et al. (2007a,b); Repicky et al. (2005).

Experimental

Crystal data

C₁₀H₁₁N₂⁺·HSO₄^-·2H₂O
M_r = 292.32
Triclinic, $[P \overline 1]$
a = 10.1585 (9) Å
b = 11.2131 (9) Å
c = 13.3545 (11) Å
= 68.283 (6)°
= 76.355 (7)°
= 67.949 (6)°
V = 1301.51 (19) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 120 (2) K
0.5 × 0.15 × 0.12 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) T_min = 0.950, T_max = 0.970
16357 measured reflections
7008 independent reflections
5729 reflections with I > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.182
S = 1.06
7008 reflections
409 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.99 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO7ⁱ	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1-H1CO7ⁱⁱ	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1-H1CO8ⁱⁱ	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1-H1DO9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2-H2BO11ⁱⁱⁱ	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3-H3BO3^iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3-H3CO3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3-H3CO4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4-H4BO12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5-H5O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9-H9DO8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9-H9EO6^v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10-H10AO4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10-H10BO2^vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11-H11BO2^vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11-H11CO7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12-H12BO3^vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12-H12CO11ⁱⁱ	0.92 (4)	1.90 (4)	2.823 (3)	177 (4)
Symmetry codes: (i) -x-1, -y, -z+1; (ii) x-1, y+1, z; (iii) x, y+1, z; (iv) -x, -y+1, -z; (v) -x, -y, -z+1; (vi) -x, -y, -z; (vii) x-1, y, z.

Data collection: X-RED32 (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2193 ).

Acknowledgements

The authors acknowledge Shahid Beheshti University for financial support.

References

Amini, M. M., Mohammadnezhad, G. S. & Khavasi, H. R. (2007b). Acta Cryst. E63, m2516.
Amini, M. M., Nasiri, S. & Ng, S. W. (2007a). Acta Cryst. E63, o1361-o1362.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Repicky, A., Jantova, S., Theiszova, M. & Milata, V. (2005). Biomed. Pap. Med. Fac. Univ. Palacky Olomouc Czech. Rep. 49, 345-347.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Stoe & Cie (2005). X-RED32 (Version 1.28b), X-SHAPE (Version 2.05) and X-AREA (Version 1.31). Stoe & Cie, Darmstadt, Germany.

organic compounds