Home The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
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The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br

  • Zhao Bo EMAIL logo and Zhang Shilu
Published/Copyright: September 1, 2018

Abstract

C17H21O2N2Br, orthorhombic, Pbcn (no. 36), a = 20.179(12) Å, b = 10.902(7) Å, c = 15.026(9) Å, V = 3306(3) Å3, Z = 8, Rgt(F) = 0.0465, wRref(F2) = 0.1276, T = 296(2) K.

CCDC no.: 1584455

The crystal structure is shown in the figure. Hydrogen atoms are omitted for clarity. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Crystal collection and handling.

Crystal:Rod, yellow
Size:0.28 × 0.25 × 0.18 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:2.496 mm−1
Diffractometer, scan mode:Bruker APEX II, Φ and ω-scans
θmax, completeness:26.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:17024, 3243, 0.0864
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 1923
N(param)refined:200
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
Br10.66944(2)0.55079(4)0.05020(3)0.0648(2)
O10.57046(12)0.94773(19)0.17491(16)0.0404(6)
O20.41762(15)0.5944(3)0.27339(19)0.0609(8)
H20.39150.57820.31350.091
N10.44788(13)0.8954(2)0.10058(17)0.0333(7)
N20.43354(15)0.6996(2)0.10192(19)0.0386(7)
C10.53344(19)1.0427(3)0.1458(2)0.0362(9)
C20.5533(2)1.1630(3)0.1508(3)0.0475(10)
H2A0.59381.18230.17680.057
C30.5139(2)1.2549(3)0.1180(3)0.0535(11)
H3A0.52831.33580.12150.064
C40.4547(2)1.2298(3)0.0807(3)0.0501(11)
H4A0.42911.29360.05820.060
C50.4312(2)1.1098(3)0.0751(2)0.0394(9)
C60.47233(18)1.0153(3)0.1083(2)0.0336(8)
C70.3685(2)1.0820(4)0.0371(3)0.0488(11)
H7A0.34211.14610.01680.059
C80.3463(2)0.9677(4)0.0295(3)0.0514(11)
H8A0.30510.95200.00410.062
C90.38627(19)0.8709(3)0.0607(2)0.0402(9)
C100.3786(2)0.7473(4)0.0621(3)0.0466(10)
H10A0.34260.70340.04010.056
C110.47459(18)0.7878(3)0.1253(2)0.0335(8)
H11A0.51500.77740.15400.040
C120.4433(2)0.5707(3)0.1214(3)0.0459(10)
H12A0.48940.55660.13670.055
H12B0.43310.52250.06890.055
C130.4001(2)0.5302(3)0.1970(3)0.0541(11)
H13A0.35400.54570.18270.065
H13B0.40550.44280.20690.065
C140.63712(19)0.9720(3)0.2039(2)0.0391(9)
H14A0.63641.01820.25900.047
H14B0.66021.02020.15930.047
C150.67182(18)0.8534(3)0.2176(3)0.0423(9)
H15A0.67480.81040.16120.051
H15B0.64610.80300.25800.051
C160.74048(19)0.8705(3)0.2549(3)0.0514(11)
H16A0.76660.91830.21330.062
H16B0.73760.91650.31000.062
C170.7748(3)0.7521(4)0.2723(5)0.0946(18)
H17A0.81810.76790.29600.142
H17B0.74960.70510.31450.142
H17C0.77870.70690.21780.142

Source of materials

8-Butoxyquinoline-2-carbaldehyde was prepared according to the literature [4]. The title compound was synthesized by the reaction of 8-butoxyquinoline-2-carbaldehyde (4.59 g, 20 mmol), formaldehyde (2.8 mL, 30 mmol) and 2-aminoethanol (1.20 mL, 20 mmol) in ethanol [5]. Hydrogen bromide (1 equiv) was add to the reaction mixture, which was stirred at room temperature for 12 h. The residual mixture was filtrated, and washed with ethanol and ether. The product was obtained as a yellow solid (6.04 g, 86%). 1H NMR (400 MHz, CDCl3, 25 °C): σ 10.29 (m, J = 1.2 Hz, 1H), 8.27 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.60 (t, J = 8 Hz, 1H), 7.44−7.46 (m, 1H), 7.16 (d, J = 8 Hz, 1H, Ar-H), 4.31 (t, J = 6.8 Hz, 2H), 2.02–2.09 (m, 2H), 1.57–1.65 (m, 2H), 1.05 (t, J = 7.4 Hz, 3H). 13C NMR (100 MHz, CDCl3): σ 13.81, 19.19, 30.84, 69.03, 109.58, 117.66, 119.24, 129.67, 131.30, 137.09, 140.08, 151.33, 155.61, 193.80.

Experimental details

The structure was solved by Direct Methods, and the non-hydrogen atoms were subjected to anisotropic refinement using SHELXTL package [2].

Comment

The focus of many groups has been put on designing and assemblying NHC precursor due to their potential applications [6], [7], [8], [9]. The NHC precursor containing imidazo[1,5-a]pyridinium are quite rare [10], [11], [12], [13].

The angle of N1–C11–N2 is 108.15(3)°. There is one molecule of the title compound in the asymmetric unit. Only some parameters should be mentioned: the angle of C1—O1—C14 is 118.34(3)°. The O—C bond lengths are between 1.35(4) Å and 1.43(5) Å. Hydrogen bonding is present: (d(H⋯acceptor) and d(donor⋯acceptor), donor–H⋯acceptor): O2—H2⋯Br1i (2.41, 3.2145(3) Å), 168.5°; i = −x + 1, y, −z + 1/2.

Acknowledgements

We gratefully acknowledge support by Scientific and Technological Innovation Project of Sichuan (2017063).

References

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Received: 2018-05-31
Accepted: 2018-08-09
Published Online: 2018-09-01
Published in Print: 2018-11-27

©2018 Zhao Bo et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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