4-Amino-2-methyl­quinolinium hydrogensulfate dihydrate

Amini, M.M.; Mohammadnezhad Sh., G.; Khavasi, H.R.

doi:10.1107/S1600536807063982

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o203

https://doi.org/10.1107/S1600536807063982

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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

(Received 19 November 2007; accepted 28 November 2007; online 6 December 2007)

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—H⋯O and O—H⋯O 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
α = 68.283 (6)°
β = 76.355 (7)°
γ = 67.949 (6)°
V = 1301.51 (19) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(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
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.99 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O7ⁱ	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1—H1C⋯O7ⁱⁱ	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1—H1C⋯O8ⁱⁱ	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1—H1D⋯O9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2—H2B⋯O11ⁱⁱⁱ	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3—H3B⋯O3^iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3—H3C⋯O3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3—H3C⋯O4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4—H4B⋯O12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5—H5⋯O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9—H9D⋯O8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9—H9E⋯O6^v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10—H10A⋯O4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10—H10B⋯O2^vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11—H11B⋯O2^vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11—H11C⋯O7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12—H12B⋯O3^vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12—H12C⋯O11ⁱⁱ	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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063982/om2193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063982/om2193Isup2.hkl

checkCIF report

Comment top

In continuation of our research on the structure determination of simple ammonium salts (Amini et al., 2007a) as precursors for synthesis of double sulfate (Amini et al., 2007b), we have found that the this compound (Fig. 1) forms structures with extended hydrogen bonding in the presence of water molecules. From the packing diagram (Fig. 2), it seems that the intermolecular and intramolecular N—H···O and O—H···O and O—H···O hydrogen bonds (Table 1) are effective in the stabilization of the crystal structure. These compounds could be classified as an outstanding model system for polymers with higher dimensional hydrogen bonding. 4-aminoquinoline derivatives have cytotoxic activity (Repicky et al., 2005), so determination of molecular structure of these compounds could be beneficial. As it is shown in Fig. 2, the quinoline rings form π bonding stacks. The closest contact distance between adjacent aromatic rings is 3.328 (3) A°.

Related literature top

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

Experimental top

2-methylquinolin-4-amine (1.58 g, 0.01 mol) was dissolved in 30 ml dichloromethane. Dropwise addition of concentrated sulfuric acid (0.98 g, 0.01 mol) resulted in a white precipitate which was filtered and dissolved in methanol. Needle shape crystals were grown by slow evaporation of a methanol solution at room temperature.

Structure description top

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

Computing details top

Data collection: X-RED32 (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. Molecular structure. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. Unit-cell packing diagram as viewed down the a-direction. Hydrogen bonds are shown as dashed lines.

4-Amino-2-methylquinolinium hydrogensulfate dihydrate top

Crystal data top

C₁₀H₁₁N₂⁺·HSO₄⁻·2H₂O	Z = 4
M_r = 292.32	F(000) = 616
Triclinic, P1	D_x = 1.492 Mg m⁻³
a = 10.1585 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2131 (9) Å	Cell parameters from 2500 reflections
c = 13.3545 (11) Å	θ = 1.7–29.2°
α = 68.283 (6)°	µ = 0.27 mm⁻¹
β = 76.355 (7)°	T = 120 K
γ = 67.949 (6)°	Needle, colorless
V = 1301.51 (19) Å³	0.5 × 0.15 × 0.12 mm

Data collection top

Stoe IPDSII diffractometer	5729 reflections with I > 2σ(I)
ω scans	R_int = 0.087
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	θ_max = 29.2°, θ_min = 1.7°
T_min = 0.950, T_max = 0.970	h = −13→13
16357 measured reflections	k = −15→15
7008 independent reflections	l = −18→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.0853P)² + 1.1102P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.182	(Δ/σ)_max = 0.019
S = 1.06	Δρ_max = 0.39 e Å⁻³
7008 reflections	Δρ_min = −0.99 e Å⁻³
409 parameters

Crystal data top

C₁₀H₁₁N₂⁺·HSO₄⁻·2H₂O	γ = 67.949 (6)°
M_r = 292.32	V = 1301.51 (19) Å³
Triclinic, P1	Z = 4
a = 10.1585 (9) Å	Mo Kα radiation
b = 11.2131 (9) Å	µ = 0.27 mm⁻¹
c = 13.3545 (11) Å	T = 120 K
α = 68.283 (6)°	0.5 × 0.15 × 0.12 mm
β = 76.355 (7)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.39 e Å⁻³
7008 reflections	Δρ_min = −0.99 e Å⁻³
409 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.2667 (2)	0.3412 (2)	0.37942 (17)	0.0230 (4)
H1A	−0.1789	0.3565	0.3583	0.028*
C2	−0.2725 (2)	0.2116 (2)	0.42028 (19)	0.0251 (4)
H2A	−0.1882	0.1389	0.4268	0.03*
C3	−0.4052 (2)	0.1875 (2)	0.45255 (19)	0.0251 (4)
H3A	−0.408	0.0991	0.48	0.03*
C4	−0.5305 (2)	0.2943 (2)	0.44357 (17)	0.0228 (4)
H4A	−0.6174	0.2772	0.4648	0.027*
C5	−0.5292 (2)	0.4296 (2)	0.40258 (16)	0.0206 (4)
C6	−0.6557 (2)	0.5461 (2)	0.39237 (17)	0.0208 (4)
C7	−0.6404 (2)	0.6757 (2)	0.34890 (17)	0.0228 (4)
H7	−0.7215	0.7519	0.3411	0.027*
C8	−0.5072 (2)	0.6914 (2)	0.31778 (17)	0.0217 (4)
C9	−0.4852 (3)	0.8274 (2)	0.27189 (19)	0.0274 (5)
H9C	−0.4342	0.8368	0.2005	0.033*
H9B	−0.4311	0.8351	0.3179	0.033*
H9A	−0.5764	0.8973	0.2679	0.033*
C10	−0.3942 (2)	0.4510 (2)	0.36953 (17)	0.0205 (4)
C11	−0.7437 (2)	0.6655 (2)	0.12158 (18)	0.0240 (4)
H11A	−0.8339	0.6553	0.1415	0.029*
C12	−0.7303 (2)	0.7924 (2)	0.08060 (19)	0.0268 (4)
H12A	−0.8116	0.8683	0.0736	0.032*
C13	−0.5935 (2)	0.8088 (2)	0.04894 (19)	0.0257 (4)
H13	−0.5854	0.8953	0.0208	0.031*
C14	−0.4726 (2)	0.6974 (2)	0.05956 (17)	0.0230 (4)
H14	−0.3832	0.7093	0.0386	0.028*
C15	−0.4823 (2)	0.5647 (2)	0.10199 (16)	0.0203 (4)
C16	−0.3599 (2)	0.4439 (2)	0.11442 (17)	0.0202 (4)
C17	−0.3833 (2)	0.3176 (2)	0.15913 (17)	0.0217 (4)
H17	−0.3055	0.2385	0.1688	0.026*
C18	−0.5200 (2)	0.3094 (2)	0.18876 (17)	0.0216 (4)
C19	−0.5493 (2)	0.1767 (2)	0.23516 (18)	0.0253 (4)
H19A	−0.4617	0.1044	0.253	0.03*
H19B	−0.5889	0.1641	0.1827	0.03*
H19C	−0.6159	0.1767	0.2995	0.03*
C20	−0.6205 (2)	0.5506 (2)	0.13349 (17)	0.0207 (4)
N1	−0.7861 (2)	0.5326 (2)	0.42328 (17)	0.0264 (4)
H1B	−0.799 (3)	0.452 (3)	0.450 (2)	0.035 (8)*
H1C	−0.863 (3)	0.604 (3)	0.421 (2)	0.034 (8)*
N2	−0.38895 (19)	0.58169 (19)	0.32826 (15)	0.0215 (4)
H2B	−0.297 (3)	0.591 (3)	0.304 (2)	0.033 (8)*
N3	−0.2264 (2)	0.4497 (2)	0.08604 (16)	0.0241 (4)
H3B	−0.206 (3)	0.528 (3)	0.056 (3)	0.041 (9)*
H3C	−0.156 (3)	0.375 (3)	0.090 (2)	0.030 (7)*
N4	−0.63363 (19)	0.42260 (19)	0.17560 (15)	0.0217 (4)
H4B	−0.724 (3)	0.421 (3)	0.197 (2)	0.024 (7)*
O1	0.21598 (18)	0.09186 (18)	0.12957 (15)	0.0304 (4)
H1D	0.174 (4)	0.085 (4)	0.196 (3)	0.049 (10)*
O2	0.19440 (18)	0.16254 (17)	−0.05753 (13)	0.0285 (4)
O3	0.11031 (19)	0.33038 (17)	0.03498 (15)	0.0316 (4)
O4	−0.02002 (17)	0.17733 (17)	0.07138 (14)	0.0279 (4)
O5	−0.21953 (18)	−0.06596 (18)	0.35374 (15)	0.0299 (4)
H5	−0.169 (4)	−0.059 (4)	0.284 (3)	0.054 (10)*
O6	−0.20017 (18)	−0.15065 (18)	0.54201 (14)	0.0307 (4)
O7	−0.10350 (19)	−0.30542 (17)	0.43617 (14)	0.0306 (4)
O8	0.01481 (18)	−0.14707 (19)	0.41604 (15)	0.0328 (4)
O9	0.1039 (3)	0.0757 (2)	0.31884 (16)	0.0445 (5)
H9D	0.080 (4)	0.007 (4)	0.356 (3)	0.056 (11)*
H9E	0.133 (4)	0.098 (4)	0.358 (3)	0.047 (10)*
O10	−0.0982 (2)	−0.0478 (2)	0.16311 (16)	0.0396 (5)
H10A	−0.073 (4)	0.026 (4)	0.129 (3)	0.050 (10)*
H10B	−0.127 (4)	−0.073 (3)	0.124 (3)	0.042 (9)*
O11	−0.12512 (18)	−0.36765 (18)	0.25826 (15)	0.0276 (4)
H11C	−0.112 (3)	−0.346 (3)	0.309 (3)	0.038 (8)*
H11B	−0.137 (4)	−0.303 (4)	0.203 (3)	0.070 (13)*
O12	−0.90519 (19)	0.4039 (2)	0.21908 (16)	0.0316 (4)
H12B	−0.916 (4)	0.386 (4)	0.165 (3)	0.058 (11)*
H12C	−0.979 (4)	0.478 (4)	0.231 (3)	0.063 (11)*
S1	0.12067 (5)	0.19469 (5)	0.04176 (4)	0.02081 (14)
S2	−0.12161 (5)	−0.17207 (5)	0.44180 (4)	0.02107 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0200 (10)	0.0298 (11)	0.0256 (10)	−0.0120 (8)	−0.0022 (8)	−0.0116 (8)
C2	0.0199 (10)	0.0276 (11)	0.0317 (11)	−0.0074 (8)	−0.0033 (8)	−0.0137 (9)
C3	0.0260 (11)	0.0250 (10)	0.0304 (11)	−0.0135 (9)	−0.0012 (8)	−0.0111 (8)
C4	0.0205 (10)	0.0282 (11)	0.0258 (10)	−0.0132 (8)	−0.0009 (8)	−0.0108 (8)
C5	0.0196 (9)	0.0262 (10)	0.0220 (9)	−0.0122 (8)	−0.0019 (7)	−0.0095 (8)
C6	0.0168 (9)	0.0281 (10)	0.0224 (9)	−0.0096 (8)	−0.0002 (7)	−0.0118 (8)
C7	0.0223 (10)	0.0237 (10)	0.0258 (10)	−0.0077 (8)	−0.0040 (8)	−0.0102 (8)
C8	0.0222 (10)	0.0240 (10)	0.0228 (9)	−0.0099 (8)	−0.0033 (7)	−0.0086 (8)
C9	0.0317 (12)	0.0254 (11)	0.0297 (11)	−0.0148 (9)	−0.0041 (9)	−0.0076 (8)
C10	0.0197 (9)	0.0247 (10)	0.0230 (9)	−0.0109 (8)	−0.0022 (7)	−0.0102 (8)
C11	0.0184 (9)	0.0310 (11)	0.0278 (10)	−0.0109 (8)	−0.0033 (8)	−0.0113 (8)
C12	0.0213 (10)	0.0281 (11)	0.0329 (11)	−0.0059 (8)	−0.0057 (8)	−0.0121 (9)
C13	0.0266 (11)	0.0245 (10)	0.0307 (11)	−0.0120 (9)	−0.0034 (9)	−0.0098 (8)
C14	0.0213 (10)	0.0275 (10)	0.0253 (10)	−0.0126 (8)	−0.0030 (8)	−0.0086 (8)
C15	0.0192 (9)	0.0264 (10)	0.0212 (9)	−0.0112 (8)	−0.0019 (7)	−0.0101 (8)
C16	0.0178 (9)	0.0268 (10)	0.0225 (9)	−0.0113 (8)	−0.0015 (7)	−0.0109 (8)
C17	0.0176 (9)	0.0252 (10)	0.0278 (10)	−0.0091 (8)	−0.0035 (8)	−0.0115 (8)
C18	0.0201 (9)	0.0260 (10)	0.0242 (10)	−0.0121 (8)	−0.0025 (7)	−0.0091 (8)
C19	0.0258 (10)	0.0272 (11)	0.0288 (11)	−0.0154 (9)	−0.0009 (8)	−0.0097 (8)
C20	0.0192 (9)	0.0251 (10)	0.0228 (9)	−0.0102 (8)	−0.0035 (7)	−0.0092 (8)
N1	0.0177 (9)	0.0285 (10)	0.0355 (10)	−0.0099 (8)	−0.0012 (7)	−0.0112 (8)
N2	0.0199 (8)	0.0259 (9)	0.0248 (8)	−0.0121 (7)	−0.0015 (7)	−0.0106 (7)
N3	0.0160 (9)	0.0269 (10)	0.0325 (10)	−0.0104 (8)	−0.0011 (7)	−0.0101 (8)
N4	0.0171 (8)	0.0292 (9)	0.0255 (9)	−0.0130 (7)	−0.0011 (6)	−0.0109 (7)
O1	0.0226 (8)	0.0384 (10)	0.0315 (9)	−0.0084 (7)	−0.0048 (7)	−0.0127 (7)
O2	0.0302 (8)	0.0337 (9)	0.0284 (8)	−0.0149 (7)	0.0030 (6)	−0.0162 (7)
O3	0.0305 (9)	0.0282 (8)	0.0435 (10)	−0.0172 (7)	0.0046 (7)	−0.0167 (7)
O4	0.0183 (7)	0.0330 (9)	0.0387 (9)	−0.0157 (7)	−0.0021 (6)	−0.0111 (7)
O5	0.0238 (8)	0.0329 (9)	0.0346 (9)	−0.0071 (7)	−0.0045 (7)	−0.0135 (7)
O6	0.0300 (9)	0.0380 (9)	0.0305 (8)	−0.0175 (7)	0.0027 (7)	−0.0148 (7)
O7	0.0325 (9)	0.0268 (8)	0.0367 (9)	−0.0127 (7)	−0.0027 (7)	−0.0121 (7)
O8	0.0206 (8)	0.0443 (10)	0.0398 (10)	−0.0194 (7)	−0.0011 (7)	−0.0124 (8)
O9	0.0656 (14)	0.0587 (13)	0.0308 (10)	−0.0463 (12)	0.0001 (9)	−0.0143 (9)
O10	0.0614 (13)	0.0439 (11)	0.0288 (9)	−0.0365 (10)	−0.0023 (8)	−0.0099 (8)
O11	0.0253 (8)	0.0320 (9)	0.0328 (9)	−0.0150 (7)	−0.0018 (7)	−0.0130 (7)
O12	0.0208 (8)	0.0380 (10)	0.0445 (10)	−0.0133 (7)	−0.0023 (7)	−0.0191 (8)
S1	0.0171 (3)	0.0242 (3)	0.0272 (3)	−0.0123 (2)	−0.00033 (19)	−0.0103 (2)
S2	0.0170 (3)	0.0253 (3)	0.0263 (3)	−0.0114 (2)	−0.00057 (19)	−0.0105 (2)

Geometric parameters (Å, º) top

C1—C2	1.369 (3)	C16—C17	1.407 (3)
C1—C10	1.405 (3)	C17—C18	1.380 (3)
C1—H1A	0.93	C17—H17	0.93
C2—C3	1.411 (3)	C18—N4	1.344 (3)
C2—H2A	0.93	C18—C19	1.499 (3)
C3—C4	1.374 (3)	C19—H19A	0.96
C3—H3A	0.93	C19—H19B	0.96
C4—C5	1.414 (3)	C19—H19C	0.96
C4—H4A	0.93	C20—N4	1.380 (3)
C5—C10	1.420 (3)	N1—H1B	0.89 (3)
C5—C6	1.437 (3)	N1—H1C	0.89 (3)
C6—N1	1.339 (3)	N2—H2B	0.95 (3)
C6—C7	1.406 (3)	N3—H3B	0.90 (3)
C7—C8	1.376 (3)	N3—H3C	0.86 (3)
C7—H7	0.93	N4—H4B	0.90 (3)
C8—N2	1.348 (3)	O1—S1	1.5293 (18)
C8—C9	1.500 (3)	O1—H1D	0.87 (4)
C9—H9C	0.96	O2—S1	1.4601 (17)
C9—H9B	0.96	O3—S1	1.4548 (16)
C9—H9A	0.96	O4—S1	1.4568 (15)
C10—N2	1.379 (3)	O5—S2	1.5543 (18)
C11—C12	1.370 (3)	O5—H5	0.94 (4)
C11—C20	1.408 (3)	O6—S2	1.4406 (17)
C11—H11A	0.93	O7—S2	1.4646 (17)
C12—C13	1.414 (3)	O8—S2	1.4536 (15)
C12—H12A	0.93	O9—H9D	0.84 (4)
C13—C14	1.374 (3)	O9—H9E	0.81 (4)
C13—H13	0.93	O10—H10A	0.88 (4)
C14—C15	1.415 (3)	O10—H10B	0.82 (3)
C14—H14	0.93	O11—H11C	0.85 (3)
C15—C20	1.419 (3)	O11—H11B	0.82 (4)
C15—C16	1.440 (3)	O12—H12B	0.86 (4)
C16—N3	1.339 (2)	O12—H12C	0.92 (4)

C2—C1—C10	119.60 (19)	N3—C16—C17	120.0 (2)
C2—C1—H1A	120.2	N3—C16—C15	121.66 (19)
C10—C1—H1A	120.2	C17—C16—C15	118.32 (18)
C1—C2—C3	120.6 (2)	C18—C17—C16	121.0 (2)
C1—C2—H2A	119.7	C18—C17—H17	119.5
C3—C2—H2A	119.7	C16—C17—H17	119.5
C4—C3—C2	120.19 (19)	N4—C18—C17	120.30 (19)
C4—C3—H3A	119.9	N4—C18—C19	117.20 (18)
C2—C3—H3A	119.9	C17—C18—C19	122.5 (2)
C3—C4—C5	121.01 (19)	C18—C19—H19A	109.5
C3—C4—H4A	119.5	C18—C19—H19B	109.5
C5—C4—H4A	119.5	H19A—C19—H19B	109.5
C4—C5—C10	117.63 (19)	C18—C19—H19C	109.5
C4—C5—C6	124.08 (18)	H19A—C19—H19C	109.5
C10—C5—C6	118.30 (18)	H19B—C19—H19C	109.5
N1—C6—C7	120.1 (2)	N4—C20—C11	119.97 (18)
N1—C6—C5	121.16 (19)	N4—C20—C15	119.33 (19)
C7—C6—C5	118.71 (18)	C11—C20—C15	120.70 (19)
C8—C7—C6	120.9 (2)	C6—N1—H1B	122 (2)
C8—C7—H7	119.6	C6—N1—H1C	120.9 (19)
C6—C7—H7	119.6	H1B—N1—H1C	117 (3)
N2—C8—C7	120.14 (19)	C8—N2—C10	122.78 (17)
N2—C8—C9	116.95 (18)	C8—N2—H2B	121.3 (18)
C7—C8—C9	122.9 (2)	C10—N2—H2B	115.9 (18)
C8—C9—H9C	109.5	C16—N3—H3B	123 (2)
C8—C9—H9B	109.5	C16—N3—H3C	118.9 (19)
H9C—C9—H9B	109.5	H3B—N3—H3C	118 (3)
C8—C9—H9A	109.5	C18—N4—C20	122.61 (17)
H9C—C9—H9A	109.5	C18—N4—H4B	122.8 (17)
H9B—C9—H9A	109.5	C20—N4—H4B	114.6 (17)
N2—C10—C1	119.84 (18)	S1—O1—H1D	114 (2)
N2—C10—C5	119.20 (19)	S2—O5—H5	111 (2)
C1—C10—C5	120.96 (19)	H9D—O9—H9E	109 (4)
C12—C11—C20	119.83 (19)	H10A—O10—H10B	114 (3)
C12—C11—H11A	120.1	H11C—O11—H11B	111 (3)
C20—C11—H11A	120.1	H12B—O12—H12C	111 (3)
C11—C12—C13	120.4 (2)	O3—S1—O4	110.45 (10)
C11—C12—H12A	119.8	O3—S1—O2	111.62 (10)
C13—C12—H12A	119.8	O4—S1—O2	112.86 (10)
C14—C13—C12	120.2 (2)	O3—S1—O1	108.74 (10)
C14—C13—H13	119.9	O4—S1—O1	108.47 (10)
C12—C13—H13	119.9	O2—S1—O1	104.41 (10)
C13—C14—C15	120.93 (19)	O6—S2—O8	113.87 (10)
C13—C14—H14	119.5	O6—S2—O7	112.78 (10)
C15—C14—H14	119.5	O8—S2—O7	110.74 (11)
C14—C15—C20	117.89 (19)	O6—S2—O5	104.17 (10)
C14—C15—C16	123.65 (18)	O8—S2—O5	108.13 (10)
C20—C15—C16	118.47 (18)	O7—S2—O5	106.56 (10)

C10—C1—C2—C3	0.0 (3)	C13—C14—C15—C16	179.5 (2)
C1—C2—C3—C4	−0.2 (3)	C14—C15—C16—N3	0.0 (3)
C2—C3—C4—C5	−0.3 (3)	C20—C15—C16—N3	179.79 (19)
C3—C4—C5—C10	1.0 (3)	C14—C15—C16—C17	179.10 (19)
C3—C4—C5—C6	−179.1 (2)	C20—C15—C16—C17	−1.2 (3)
C4—C5—C6—N1	0.8 (3)	N3—C16—C17—C18	−179.9 (2)
C10—C5—C6—N1	−179.22 (19)	C15—C16—C17—C18	1.0 (3)
C4—C5—C6—C7	−179.12 (19)	C16—C17—C18—N4	−0.2 (3)
C10—C5—C6—C7	0.8 (3)	C16—C17—C18—C19	179.12 (19)
N1—C6—C7—C8	179.3 (2)	C12—C11—C20—N4	179.5 (2)
C5—C6—C7—C8	−0.7 (3)	C12—C11—C20—C15	−0.9 (3)
C6—C7—C8—N2	0.3 (3)	C14—C15—C20—N4	−179.74 (18)
C6—C7—C8—C9	−179.5 (2)	C16—C15—C20—N4	0.5 (3)
C2—C1—C10—N2	−179.89 (19)	C14—C15—C20—C11	0.7 (3)
C2—C1—C10—C5	0.8 (3)	C16—C15—C20—C11	−179.10 (19)
C4—C5—C10—N2	179.44 (18)	C7—C8—N2—C10	0.1 (3)
C6—C5—C10—N2	−0.5 (3)	C9—C8—N2—C10	179.83 (18)
C4—C5—C10—C1	−1.3 (3)	C1—C10—N2—C8	−179.24 (19)
C6—C5—C10—C1	178.79 (19)	C5—C10—N2—C8	0.1 (3)
C20—C11—C12—C13	0.8 (3)	C17—C18—N4—C20	−0.5 (3)
C11—C12—C13—C14	−0.4 (3)	C19—C18—N4—C20	−179.86 (18)
C12—C13—C14—C15	0.1 (3)	C11—C20—N4—C18	179.95 (19)
C13—C14—C15—C20	−0.2 (3)	C15—C20—N4—C18	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O7ⁱ	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1—H1C···O7ⁱⁱ	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1—H1C···O8ⁱⁱ	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1—H1D···O9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2—H2B···O11ⁱⁱⁱ	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3—H3B···O3^iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3—H3C···O3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3—H3C···O4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4—H4B···O12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5—H5···O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9—H9D···O8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9—H9E···O6^v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10—H10A···O4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10—H10B···O2^vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11—H11B···O2^vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11—H11C···O7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12—H12B···O3^vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12—H12C···O11ⁱⁱ	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.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₂⁺·HSO₄⁻·2H₂O
M_r	292.32
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	10.1585 (9), 11.2131 (9), 13.3545 (11)
α, β, γ (°)	68.283 (6), 76.355 (7), 67.949 (6)
V (Å³)	1301.51 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.5 × 0.15 × 0.12

Data collection
Diffractometer	Stoe IPDSII
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.950, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	16357, 7008, 5729
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.182, 1.06
No. of reflections	7008
No. of parameters	409
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.99

Computer programs: X-RED32 (Stoe & Cie, 2005), X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O7ⁱ	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1—H1C···O7ⁱⁱ	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1—H1C···O8ⁱⁱ	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1—H1D···O9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2—H2B···O11ⁱⁱⁱ	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3—H3B···O3^iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3—H3C···O3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3—H3C···O4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4—H4B···O12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5—H5···O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9—H9D···O8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9—H9E···O6^v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10—H10A···O4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10—H10B···O2^vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11—H11B···O2^vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11—H11C···O7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12—H12B···O3^vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12—H12C···O11ⁱⁱ	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.

Acknowledgements

The authors acknowledge Shahid Beheshti University for financial support.

References

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