2-Cyano­quinolin-1-ium hydrogen sulfate

Loh, W.-S.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S160053681003878X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2709

https://doi.org/10.1107/S160053681003878X

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2-Cyanoquinolin-1-ium hydrogen sulfate

Wan-Sin Loh,^a ‡ Madhukar Hemamalini ^a and Hoong-Kun Fun ^a ^*§

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 27 September 2010; accepted 28 September 2010; online 2 October 2010)

The title salt, C₁₀H₇N₂⁺·HSO₄⁻, is formed by the transfer of a proton from H₂SO₄ to the N atom of 2-cyanoquinoline during crystallization. The quinoline ring system is approximately planar with a maximum deviation of 0.013 (3) Å. In the crystal, the cations are linked to the anions via intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, forming a layered network.

Related literature

For background to and the biological activity of quinoline derivatives, see: Loh et al. (2010a ,b); Sasaki et al. (1998 ); Reux et al. (2009 ); Morimoto et al. (1991 ); Michael (1997 ); Markees et al. (1970 ); Campbell et al. (1988 ). For related structures, see: Loh et al. (2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₀H₇N₂⁺·HSO₄⁻
M_r = 252.24
Triclinic, $[P \overline 1]$
a = 7.2154 (3) Å
b = 8.2334 (4) Å
c = 9.9985 (4) Å
α = 110.622 (2)°
β = 90.982 (3)°
γ = 110.791 (2)°
V = 512.82 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.34 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.900, T_max = 0.963
5740 measured reflections
1979 independent reflections
1721 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.154
S = 1.11
1979 reflections
186 parameters
All H-atom parameters refined
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.98 (5)	1.71 (5)	2.669 (3)	169 (4)
O4—H1O4⋯O2ⁱⁱ	0.67 (5)	1.97 (5)	2.641 (3)	176 (7)
C2—H2A⋯O2ⁱⁱⁱ	0.91 (4)	2.53 (4)	3.320 (4)	145 (3)
C5—H5A⋯O4^iv	0.98 (3)	2.52 (3)	3.475 (4)	166 (3)
C7—H7A⋯O3^iv	0.94 (4)	2.41 (4)	3.338 (4)	167 (3)
C8—H8A⋯O2^v	0.99 (4)	2.59 (4)	3.309 (4)	130 (3)
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+1; (iv) x+1, y, z+1; (v) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003878X/hb5657sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003878X/hb5657Isup2.hkl

checkCIF report

Comment top

Recently, hydrogen-bonding patterns involving quinoline and its derivatives with organic acid have been investigated (Loh at al., 2010a,b). Syntheses of the quinoline derivatives were discussed earlier (Sasaki et al., 1998; Reux et al., 2009). Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991; Michael, 1997) and biologically active compounds (Markees et al., 1970; Campbell et al., 1988). Heterocyclic molecules containing cyano group are useful as drug intermediates. Herein we report the synthesis of 2-cyanoquinolin-1-ium hydrogen sulfate.

The asymmetric unit of the title compound (Fig. 1) consists of one 2-cyanoquinolin-1-ium cation (C1–C10/N1/N2) and one hydrogen sulfate anion (O1–O4/S1). One proton is transferred from the hydroxyl group of hydrogen sulfate to the atom N1 of 2-cyanoquinoline during the crystallization, resulting in the formation of salt. The quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.013 (3) Å at atom C6. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh et al., 2010a,b).

In the crystal (Fig. 2), the cations are linked by the anions via intermolecular N1—H1N1···O1, O4—H1O4···O2, C2—H2A···O2, C5—H5A···O4, C7—H7A···O3 and C8—H8A···O2 hydrogen bonds (Table 1) into a two-dimensional networks.

Related literature top

For background to and the biological activity of quinoline derivatives, see: Loh et al. (2010a,b); Sasaki et al. (1998); Reux et al. (2009); Morimoto et al. (1991); Michael (1997); Markees et al. (1970); Campbell et al. (1988). For related structures, see: Loh et al. (2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

A few drops of sulfuric acid were added to a hot methanol solution (20 ml) of quinoline-2-carbonitrile (39 mg, Aldrich) which had been warmed over a magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly to room temperature. Colourless blocks of (I) appeared after a few days.

Structure description top

For background to and the biological activity of quinoline derivatives, see: Loh et al. (2010a,b); Sasaki et al. (1998); Reux et al. (2009); Morimoto et al. (1991); Michael (1997); Markees et al. (1970); Campbell et al. (1988). For related structures, see: Loh et al. (2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of (I), viewed along the c axis.

2-Cyanoquinolin-1-ium hydrogen sulfate top

Crystal data top

C₁₀H₇N₂⁺·HSO₄⁻	Z = 2
M_r = 252.24	F(000) = 260
Triclinic, P1	D_x = 1.634 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2154 (3) Å	Cell parameters from 2998 reflections
b = 8.2334 (4) Å	θ = 2.2–27.6°
c = 9.9985 (4) Å	µ = 0.32 mm⁻¹
α = 110.622 (2)°	T = 100 K
β = 90.982 (3)°	Block, colourless
γ = 110.791 (2)°	0.34 × 0.19 × 0.12 mm
V = 512.82 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	1979 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→6
T_min = 0.900, T_max = 0.963	k = −10→10
5740 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	All H-atom parameters refined
S = 1.11	w = 1/[σ²(F_o²) + (0.0884P)² + 0.5522P] where P = (F_o² + 2F_c²)/3
1979 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₀H₇N₂⁺·HSO₄⁻	γ = 110.791 (2)°
M_r = 252.24	V = 512.82 (4) Å³
Triclinic, P1	Z = 2
a = 7.2154 (3) Å	Mo Kα radiation
b = 8.2334 (4) Å	µ = 0.32 mm⁻¹
c = 9.9985 (4) Å	T = 100 K
α = 110.622 (2)°	0.34 × 0.19 × 0.12 mm
β = 90.982 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	1979 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1721 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.963	R_int = 0.032
5740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.154	All H-atom parameters refined
S = 1.11	Δρ_max = 0.82 e Å⁻³
1979 reflections	Δρ_min = −0.56 e Å⁻³
186 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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
S1	0.15454 (10)	0.99553 (10)	0.33365 (7)	0.0141 (3)
O1	0.3450 (3)	1.0495 (3)	0.4227 (2)	0.0216 (5)
O2	0.0561 (3)	1.1258 (3)	0.3966 (2)	0.0184 (5)
O3	0.1678 (3)	0.9584 (3)	0.1832 (2)	0.0199 (5)
O4	0.0149 (3)	0.8001 (3)	0.3345 (3)	0.0213 (5)
N1	0.5709 (4)	0.3044 (3)	0.6749 (3)	0.0153 (5)
N2	0.7421 (5)	0.4421 (4)	0.4025 (3)	0.0341 (8)
C1	0.5498 (4)	0.2853 (4)	0.8046 (3)	0.0146 (6)
C2	0.3903 (4)	0.1311 (4)	0.8119 (3)	0.0171 (6)
C3	0.3736 (5)	0.1152 (4)	0.9439 (3)	0.0176 (6)
C4	0.5161 (4)	0.2496 (4)	1.0697 (3)	0.0178 (7)
C5	0.6693 (4)	0.3999 (4)	1.0632 (3)	0.0157 (6)
C6	0.6915 (4)	0.4236 (4)	0.9298 (3)	0.0151 (6)
C7	0.8438 (4)	0.5775 (4)	0.9151 (3)	0.0161 (6)
C8	0.8587 (4)	0.5909 (4)	0.7818 (3)	0.0164 (6)
C9	0.7188 (4)	0.4485 (4)	0.6622 (3)	0.0171 (6)
C10	0.7297 (5)	0.4459 (4)	0.5172 (3)	0.0224 (7)
H2A	0.305 (5)	0.040 (5)	0.730 (4)	0.017 (8)*
H3A	0.266 (5)	0.008 (5)	0.947 (4)	0.018 (8)*
H4A	0.493 (5)	0.226 (5)	1.157 (4)	0.025 (9)*
H5A	0.767 (4)	0.498 (4)	1.148 (3)	0.008 (7)*
H7A	0.933 (5)	0.672 (5)	0.999 (4)	0.016 (8)*
H8A	0.964 (5)	0.696 (5)	0.767 (4)	0.015 (8)*
H1N1	0.474 (6)	0.211 (6)	0.589 (5)	0.045 (11)*
H1O4	−0.005 (7)	0.814 (7)	0.402 (5)	0.040 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0155 (4)	0.0150 (4)	0.0056 (4)	0.0016 (3)	−0.0029 (3)	0.0015 (3)
O1	0.0213 (11)	0.0246 (12)	0.0092 (10)	0.0065 (9)	−0.0058 (8)	−0.0016 (9)
O2	0.0221 (11)	0.0209 (11)	0.0133 (10)	0.0093 (9)	0.0018 (8)	0.0069 (9)
O3	0.0229 (11)	0.0231 (12)	0.0058 (10)	0.0025 (9)	0.0009 (8)	0.0031 (9)
O4	0.0286 (13)	0.0204 (12)	0.0079 (11)	0.0045 (10)	0.0005 (9)	0.0028 (10)
N1	0.0176 (13)	0.0158 (13)	0.0088 (12)	0.0046 (10)	−0.0020 (10)	0.0025 (10)
N2	0.0415 (18)	0.0289 (16)	0.0134 (14)	−0.0059 (14)	−0.0036 (12)	0.0070 (12)
C1	0.0183 (15)	0.0194 (15)	0.0080 (13)	0.0100 (12)	0.0014 (11)	0.0047 (12)
C2	0.0155 (14)	0.0167 (15)	0.0130 (15)	0.0041 (12)	−0.0030 (12)	0.0013 (12)
C3	0.0175 (15)	0.0185 (16)	0.0148 (15)	0.0047 (13)	−0.0003 (12)	0.0066 (13)
C4	0.0218 (16)	0.0229 (16)	0.0113 (15)	0.0116 (13)	0.0031 (12)	0.0063 (13)
C5	0.0183 (15)	0.0199 (15)	0.0079 (14)	0.0094 (13)	−0.0005 (11)	0.0023 (12)
C6	0.0159 (14)	0.0145 (15)	0.0122 (14)	0.0051 (12)	−0.0019 (11)	0.0030 (12)
C7	0.0197 (15)	0.0157 (15)	0.0093 (14)	0.0073 (12)	−0.0016 (12)	0.0004 (12)
C8	0.0154 (14)	0.0162 (15)	0.0134 (14)	0.0033 (12)	−0.0013 (11)	0.0039 (12)
C9	0.0209 (15)	0.0182 (15)	0.0113 (14)	0.0069 (12)	0.0007 (11)	0.0055 (12)
C10	0.0259 (17)	0.0183 (16)	0.0134 (16)	0.0001 (13)	−0.0026 (12)	0.0040 (13)

Geometric parameters (Å, º) top

S1—O3	1.438 (2)	C3—C4	1.425 (4)
S1—O1	1.457 (2)	C3—H3A	0.96 (3)
S1—O2	1.460 (2)	C4—C5	1.358 (4)
S1—O4	1.570 (2)	C4—H4A	0.96 (4)
O4—H1O4	0.67 (5)	C5—C6	1.418 (4)
N1—C9	1.333 (4)	C5—H5A	0.98 (3)
N1—C1	1.365 (4)	C6—C7	1.408 (4)
N1—H1N1	0.98 (5)	C7—C8	1.378 (4)
N2—C10	1.142 (4)	C7—H7A	0.95 (4)
C1—C2	1.404 (4)	C8—C9	1.398 (4)
C1—C6	1.426 (4)	C8—H8A	0.99 (3)
C2—C3	1.375 (4)	C9—C10	1.446 (4)
C2—H2A	0.91 (3)

O3—S1—O1	113.75 (13)	C5—C4—C3	120.9 (3)
O3—S1—O2	113.56 (12)	C5—C4—H4A	124 (2)
O1—S1—O2	111.77 (12)	C3—C4—H4A	115 (2)
O3—S1—O4	104.10 (13)	C4—C5—C6	120.2 (3)
O1—S1—O4	105.98 (13)	C4—C5—H5A	123.1 (17)
O2—S1—O4	106.81 (13)	C6—C5—H5A	116.7 (17)
S1—O4—H1O4	108 (4)	C7—C6—C5	123.5 (3)
C9—N1—C1	122.0 (2)	C7—C6—C1	118.5 (3)
C9—N1—H1N1	119 (3)	C5—C6—C1	118.0 (3)
C1—N1—H1N1	119 (3)	C8—C7—C6	120.6 (3)
N1—C1—C2	119.6 (3)	C8—C7—H7A	121 (2)
N1—C1—C6	118.8 (3)	C6—C7—H7A	118 (2)
C2—C1—C6	121.7 (3)	C7—C8—C9	118.4 (3)
C3—C2—C1	118.2 (3)	C7—C8—H8A	122.8 (19)
C3—C2—H2A	121 (2)	C9—C8—H8A	118.8 (19)
C1—C2—H2A	121 (2)	N1—C9—C8	121.7 (3)
C2—C3—C4	121.0 (3)	N1—C9—C10	116.2 (3)
C2—C3—H3A	117 (2)	C8—C9—C10	122.1 (3)
C4—C3—H3A	121 (2)	N2—C10—C9	178.2 (4)

C9—N1—C1—C2	179.6 (3)	C2—C1—C6—C7	−178.0 (3)
C9—N1—C1—C6	−0.5 (4)	N1—C1—C6—C5	−179.0 (2)
N1—C1—C2—C3	179.7 (3)	C2—C1—C6—C5	1.0 (4)
C6—C1—C2—C3	−0.3 (4)	C5—C6—C7—C8	179.2 (3)
C1—C2—C3—C4	−1.1 (5)	C1—C6—C7—C8	−1.9 (4)
C2—C3—C4—C5	1.8 (5)	C6—C7—C8—C9	0.2 (4)
C3—C4—C5—C6	−1.1 (4)	C1—N1—C9—C8	−1.4 (4)
C4—C5—C6—C7	178.7 (3)	C1—N1—C9—C10	176.8 (3)
C4—C5—C6—C1	−0.3 (4)	C7—C8—C9—N1	1.5 (5)
N1—C1—C6—C7	2.0 (4)	C7—C8—C9—C10	−176.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.98 (5)	1.71 (5)	2.669 (3)	169 (4)
O4—H1O4···O2ⁱⁱ	0.67 (5)	1.97 (5)	2.641 (3)	176 (7)
C2—H2A···O2ⁱⁱⁱ	0.91 (4)	2.53 (4)	3.320 (4)	145 (3)
C5—H5A···O4^iv	0.98 (3)	2.52 (3)	3.475 (4)	166 (3)
C7—H7A···O3^iv	0.94 (4)	2.41 (4)	3.338 (4)	167 (3)
C8—H8A···O2^v	0.99 (4)	2.59 (4)	3.309 (4)	130 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₇N₂⁺·HSO₄⁻
M_r	252.24
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.2154 (3), 8.2334 (4), 9.9985 (4)
α, β, γ (°)	110.622 (2), 90.982 (3), 110.791 (2)
V (Å³)	512.82 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.34 × 0.19 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.900, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	5740, 1979, 1721
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.154, 1.11
No. of reflections	1979
No. of parameters	186
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.56

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.98 (5)	1.71 (5)	2.669 (3)	169 (4)
O4—H1O4···O2ⁱⁱ	0.67 (5)	1.97 (5)	2.641 (3)	176 (7)
C2—H2A···O2ⁱⁱⁱ	0.91 (4)	2.53 (4)	3.320 (4)	145 (3)
C5—H5A···O4^iv	0.98 (3)	2.52 (3)	3.475 (4)	166 (3)
C7—H7A···O3^iv	0.94 (4)	2.41 (4)	3.338 (4)	167 (3)
C8—H8A···O2^v	0.99 (4)	2.59 (4)	3.309 (4)	130 (3)

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL thanks USM for the award of a USM fellowship and HM thanks USM for the award of a post doctoral fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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