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8-Hydroxy-5-(hydroxymethyl)quinolin-1-ium chloride
aLaboratoire de Physico-chimie des Matériaux Vitreux et Cristallisés, Equipe de Physico-chimie des Matériaux Inorganiques, Faculté des Sciences, Université Ibn Tofail, Kénitra, Morocco, bLaboratoire d'Agroressources et Génie des Procédés, Faculté des Sciences, Université Ibn Tofail Kénitra, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: elhassan.arbib@yahoo.com
The title compound, C10H10NO2+·Cl−, contains a quinoline ring system which is essentially planar, with the largest deviation from the mean plane being 0.017 (1) Å. In the crystal, the ion pairs and their inversion-symmetry-related partners are linked by N—H⋯Cl and O—H⋯Cl hydrogen bonds to form tetramers which are further connected through O—H⋯O hydrogen bonds, building infinite one-dimensional chains parallel to the [010] direction.
Related literature
For antioxidant properties, see: Kayyali et al. (1998). For the synthesis of some substituted 8-quinolinol derivatives, see: Mishra et al. (2004
). For the application of the corresponding aluminium complexes, see: Tang et al. (1989
); Chen & Shi (1998
); Shougen et al. (2000
). For application as a promising display, see: Cao et al. (1996
); Wu et al. (2003
). For the synthesis, see: Zheng et al. (2005
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: PLATON (Spek, 2009
) and publCIF (Westrip, 2010
).
Supporting information
https://doi.org/10.1107/S1600536812024233/fj2562sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024233/fj2562Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812024233/fj2562Isup3.cml
5-Chloromethyl-8-hydroxyquinoline hydrochloride (I) was synthesized according to the method described by Zheng et al. (2005). A mixture of 10.0 g (0.068 mol) of 8-hydroxyquinoline, 11 ml of concentrated hydrochloric acid, and 11 ml (0.397 mol) of 37% formaldehyde was treated with hydrogen chloride gas and stirred for 6 h. The solution was allowed to stand at room temperature for 2 h without stirring. The yellow solid obtained was collected on a filter, washed with acetone or alcohol, and dried under vacuum to give 5-chloromethyl-8-hydroxyquinoline hydrochloride (I) (13.0 g, 98%). The compound obtained was dissolved in distilled water in a box Petrys and let in air at room temperature. After 10 days, transparent single crystals as platelets were isolated. X-ray
shows that the obtained product is the 5-(hydroxymethyl)-8-quinolinol hydrochloride.H atoms were located in a difference map and treated as riding with N—H = 0.86 Å, C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and O—H = 0.82 Å with Uiso(H) = 1.2 Ueq (aromatic, methylene) and Uiso(H)= 1.5 Ueq (OH).
8-Quinolinol is a strong iron chelator with antioxidant property (Kayyali et al. 1998). 5-Chloromethyl-8-hydroxyquinoline hydrochloride (I) is used as an intermediate in the synthesis of 5-hydroxymethyl-8-quinolinol and some substituted 8-quinolinol derivatives (Mishra et al. (2004). The corresponding aluminium complexes has been used as an excellent Organic Light-Emitting Diodes (OLEDs) (Tang et al. (1989), Chen & Shi (1998), Shougen et al. (2000)) witch are currently under intensive investigation for application as a promising display technology due to their high luminous efficiency and capability of emitting full colour flat displays (Cao et al. (1996), Wu et al. (2003)). The present work describes the
of C10H10NO2.Cl (scheme 1) obtained from the X-ray diffraction data on single-crystal.The 5-(hydroxymethyl)-8-quinolinol hydrochloride molecule structure is built up from two fused six-membered rings linked to CH2OH and to OH groups as shown in Fg.1. The fused-ring system is essentially planar, with the maximum deviation of 0.017 (1) Å from C7 atom. The dihedral angle between them does not exceed 1.15 (5)°. The hydroxide O2—H linked to –C10H2– form an angle of 56.68 (6) ° with the mean plane of the quinolin ring. In the crystal, each molecule and its symmetry through the inversion center are linked by N—H···Cl and O—H···Cl hydrogen bonds in the way to form dimers as shown in Fig.2. These dimers are further connected through O—H···O hydrogen bonds building infinite one-dimensional chains parallel to [0 1 0] direction (Table 1).
For antioxidant properties, see: Kayyali et al. (1998). For the synthesis of some substituted 8-quinolinol derivatives, see: Mishra et al. (2004). For the application of the corresponding aluminium complexes, see: Tang et al. (1989); Chen & Shi (1998); Shougen et al. (2000). For application as a promising display, see: Cao et al. (1996); Wu et al. (2003). For the synthesis, see: Zheng et al. (2005).
Data collection: APEX2 (Bruker, 2005); cell
APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).C10H10NO2+·Cl− | F(000) = 440 |
Mr = 211.64 | Dx = 1.498 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p_2ybc | Cell parameters from 4615 reflections |
a = 6.9081 (5) Å | θ = 2.8–36.5° |
b = 8.0577 (5) Å | µ = 0.38 mm−1 |
c = 17.1890 (11) Å | T = 296 K |
β = 101.183 (3)° | Needle, colourless |
V = 938.63 (11) Å3 | 0.54 × 0.43 × 0.12 mm |
Z = 4 |
Bruker X8 APEX diffractometer | 3679 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 36.5°, θmin = 2.8° |
φ and ω scans | h = −11→11 |
22727 measured reflections | k = −12→13 |
4615 independent reflections | l = −28→28 |
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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1142P] where P = (Fo2 + 2Fc2)/3 |
4615 reflections | (Δ/σ)max = 0.001 |
127 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C10H10NO2+·Cl− | V = 938.63 (11) Å3 |
Mr = 211.64 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.9081 (5) Å | µ = 0.38 mm−1 |
b = 8.0577 (5) Å | T = 296 K |
c = 17.1890 (11) Å | 0.54 × 0.43 × 0.12 mm |
β = 101.183 (3)° |
Bruker X8 APEX diffractometer | 3679 reflections with I > 2σ(I) |
22727 measured reflections | Rint = 0.024 |
4615 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.50 e Å−3 |
4615 reflections | Δρmin = −0.20 e Å−3 |
127 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.16928 (4) | 0.17354 (3) | 0.310398 (15) | 0.03843 (8) | |
O1 | 0.30276 (12) | 0.22164 (9) | 0.51946 (4) | 0.03652 (16) | |
H1O | 0.3342 | 0.1525 | 0.5547 | 0.055* | |
O2 | 0.44071 (12) | 0.98428 (9) | 0.61542 (5) | 0.03859 (17) | |
H2O | 0.5509 | 0.9455 | 0.6316 | 0.058* | |
N1 | 0.19725 (11) | 0.47152 (9) | 0.41916 (4) | 0.02749 (14) | |
H1N | 0.1996 | 0.3699 | 0.4041 | 0.033* | |
C1 | 0.14320 (16) | 0.58746 (13) | 0.36492 (5) | 0.03366 (18) | |
H1 | 0.1075 | 0.5578 | 0.3118 | 0.040* | |
C2 | 0.13937 (16) | 0.75383 (12) | 0.38682 (6) | 0.0362 (2) | |
H2 | 0.1026 | 0.8355 | 0.3486 | 0.043* | |
C3 | 0.19059 (14) | 0.79558 (11) | 0.46549 (6) | 0.03077 (17) | |
H3 | 0.1887 | 0.9064 | 0.4804 | 0.037* | |
C4 | 0.24629 (12) | 0.67260 (10) | 0.52439 (5) | 0.02444 (14) | |
C5 | 0.24952 (12) | 0.50630 (10) | 0.49814 (5) | 0.02361 (14) | |
C6 | 0.30430 (13) | 0.37354 (10) | 0.55186 (5) | 0.02688 (15) | |
C7 | 0.35081 (16) | 0.40924 (12) | 0.63135 (5) | 0.03253 (18) | |
H7 | 0.3846 | 0.3239 | 0.6679 | 0.039* | |
C8 | 0.34767 (16) | 0.57403 (12) | 0.65797 (5) | 0.03347 (18) | |
H8 | 0.3807 | 0.5948 | 0.7121 | 0.040* | |
C9 | 0.29775 (14) | 0.70577 (11) | 0.60713 (5) | 0.02761 (15) | |
C10 | 0.29652 (17) | 0.87978 (12) | 0.63908 (6) | 0.03501 (19) | |
H10A | 0.1669 | 0.9279 | 0.6209 | 0.042* | |
H10B | 0.3200 | 0.8753 | 0.6965 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.04035 (14) | 0.03721 (14) | 0.03423 (12) | 0.00236 (9) | −0.00147 (9) | −0.00972 (8) |
O1 | 0.0523 (4) | 0.0204 (3) | 0.0344 (3) | 0.0019 (3) | 0.0024 (3) | 0.0011 (2) |
O2 | 0.0372 (4) | 0.0224 (3) | 0.0521 (4) | −0.0014 (2) | −0.0014 (3) | 0.0061 (3) |
N1 | 0.0306 (3) | 0.0242 (3) | 0.0260 (3) | −0.0013 (2) | 0.0016 (2) | −0.0007 (2) |
C1 | 0.0395 (5) | 0.0317 (4) | 0.0265 (4) | −0.0006 (3) | −0.0018 (3) | 0.0027 (3) |
C2 | 0.0431 (5) | 0.0286 (4) | 0.0326 (4) | 0.0007 (4) | −0.0034 (4) | 0.0066 (3) |
C3 | 0.0334 (4) | 0.0218 (3) | 0.0342 (4) | 0.0001 (3) | −0.0006 (3) | 0.0035 (3) |
C4 | 0.0243 (3) | 0.0209 (3) | 0.0274 (3) | −0.0018 (2) | 0.0033 (3) | 0.0011 (2) |
C5 | 0.0242 (3) | 0.0209 (3) | 0.0251 (3) | −0.0015 (2) | 0.0034 (2) | 0.0013 (2) |
C6 | 0.0304 (4) | 0.0207 (3) | 0.0289 (3) | −0.0018 (3) | 0.0043 (3) | 0.0028 (3) |
C7 | 0.0432 (5) | 0.0253 (4) | 0.0277 (4) | −0.0024 (3) | 0.0037 (3) | 0.0053 (3) |
C8 | 0.0450 (5) | 0.0295 (4) | 0.0254 (3) | −0.0046 (4) | 0.0057 (3) | 0.0009 (3) |
C9 | 0.0317 (4) | 0.0232 (3) | 0.0280 (3) | −0.0040 (3) | 0.0060 (3) | −0.0014 (3) |
C10 | 0.0425 (5) | 0.0263 (4) | 0.0369 (4) | −0.0026 (3) | 0.0094 (4) | −0.0061 (3) |
O1—C6 | 1.3439 (11) | C3—H3 | 0.9300 |
O1—H1O | 0.8200 | C4—C5 | 1.4155 (11) |
O2—C10 | 1.4225 (13) | C4—C9 | 1.4229 (12) |
O2—H2O | 0.8200 | C5—C6 | 1.4158 (11) |
N1—C1 | 1.3215 (12) | C6—C7 | 1.3721 (13) |
N1—C5 | 1.3644 (11) | C7—C8 | 1.4059 (14) |
N1—H1N | 0.8600 | C7—H7 | 0.9300 |
C1—C2 | 1.3941 (14) | C8—C9 | 1.3757 (13) |
C1—H1 | 0.9300 | C8—H8 | 0.9300 |
C2—C3 | 1.3718 (14) | C9—C10 | 1.5065 (12) |
C2—H2 | 0.9300 | C10—H10A | 0.9700 |
C3—C4 | 1.4155 (12) | C10—H10B | 0.9700 |
C6—O1—H1O | 109.5 | C4—C5—C6 | 121.75 (7) |
C10—O2—H2O | 109.5 | O1—C6—C7 | 125.81 (8) |
C1—N1—C5 | 122.74 (8) | O1—C6—C5 | 115.99 (8) |
C1—N1—H1N | 118.6 | C7—C6—C5 | 118.19 (8) |
C5—N1—H1N | 118.6 | C6—C7—C8 | 120.44 (8) |
N1—C1—C2 | 120.45 (9) | C6—C7—H7 | 119.8 |
N1—C1—H1 | 119.8 | C8—C7—H7 | 119.8 |
C2—C1—H1 | 119.8 | C9—C8—C7 | 122.67 (8) |
C3—C2—C1 | 119.16 (8) | C9—C8—H8 | 118.7 |
C3—C2—H2 | 120.4 | C7—C8—H8 | 118.7 |
C1—C2—H2 | 120.4 | C8—C9—C4 | 118.25 (8) |
C2—C3—C4 | 121.05 (8) | C8—C9—C10 | 120.34 (8) |
C2—C3—H3 | 119.5 | C4—C9—C10 | 121.41 (8) |
C4—C3—H3 | 119.5 | O2—C10—C9 | 113.14 (8) |
C3—C4—C5 | 116.98 (8) | O2—C10—H10A | 109.0 |
C3—C4—C9 | 124.33 (8) | C9—C10—H10A | 109.0 |
C5—C4—C9 | 118.69 (7) | O2—C10—H10B | 109.0 |
N1—C5—C4 | 119.60 (7) | C9—C10—H10B | 109.0 |
N1—C5—C6 | 118.65 (7) | H10A—C10—H10B | 107.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl1 | 0.86 | 2.24 | 3.0261 (8) | 152 |
O1—H1O···O2i | 0.82 | 1.78 | 2.5841 (10) | 166 |
O2—H2O···Cl1ii | 0.82 | 2.21 | 3.0281 (8) | 172 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H10NO2+·Cl− |
Mr | 211.64 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.9081 (5), 8.0577 (5), 17.1890 (11) |
β (°) | 101.183 (3) |
V (Å3) | 938.63 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.54 × 0.43 × 0.12 |
Data collection | |
Diffractometer | Bruker X8 APEX |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22727, 4615, 3679 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.838 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.124, 1.07 |
No. of reflections | 4615 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.20 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl1 | 0.86 | 2.24 | 3.0261 (8) | 152 |
O1—H1O···O2i | 0.82 | 1.78 | 2.5841 (10) | 166 |
O2—H2O···Cl1ii | 0.82 | 2.21 | 3.0281 (8) | 172 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
References
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, Y., Parker, I. D., Yu, G., Zhang, C. & Heeger, A. J. (1996). Nature, 397, 414–417. Google Scholar
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161–174. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kayyali, R., Pannala, A. S., Khodr, H. & Hider, R. C. (1998). Biochem. Pharmacol. 55 1327–1332. Web of Science CrossRef CAS PubMed Google Scholar
Mishra, A., Nayak, P. K. & Periasamy, N. (2004). Tetrahedron Lett. 45, 6265–6268. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shougen, Y., Yulin, H., Xiaohong, C., Xiaohui, Y., Yanbing, H. & Xurong, X. (2000). Synth. Met. 111–112, 109–112. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, C. W., Vanslyke, S. A. & Chen, C. H. (1989). J. Appl. Phys. 65, 3610–3616. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, Z., Yang, H., Duan, Y., Xie, W., Liu, S. & Zhao, Y. (2003). Semicond. Sci. Technol. 18, 49–52. Web of Science CrossRef Google Scholar
Zheng, H., Weiner, L. M., Bar-Am, O., Epsztejn, S., Cabantchik, Z. I., Warshawsky, A., Youdim, M. B. H. & Fridkin, M. (2005). Bioorg. Med. Chem. 13, 773–783. Web of Science CrossRef PubMed CAS Google Scholar
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8-Quinolinol is a strong iron chelator with antioxidant property (Kayyali et al. 1998). 5-Chloromethyl-8-hydroxyquinoline hydrochloride (I) is used as an intermediate in the synthesis of 5-hydroxymethyl-8-quinolinol and some substituted 8-quinolinol derivatives (Mishra et al. (2004). The corresponding aluminium complexes has been used as an excellent Organic Light-Emitting Diodes (OLEDs) (Tang et al. (1989), Chen & Shi (1998), Shougen et al. (2000)) witch are currently under intensive investigation for application as a promising display technology due to their high luminous efficiency and capability of emitting full colour flat displays (Cao et al. (1996), Wu et al. (2003)). The present work describes the crystal structure of C10H10NO2.Cl (scheme 1) obtained from the X-ray diffraction data on single-crystal.
The 5-(hydroxymethyl)-8-quinolinol hydrochloride molecule structure is built up from two fused six-membered rings linked to CH2OH and to OH groups as shown in Fg.1. The fused-ring system is essentially planar, with the maximum deviation of 0.017 (1) Å from C7 atom. The dihedral angle between them does not exceed 1.15 (5)°. The hydroxide O2—H linked to –C10H2– form an angle of 56.68 (6) ° with the mean plane of the quinolin ring. In the crystal, each molecule and its symmetry through the inversion center are linked by N—H···Cl and O—H···Cl hydrogen bonds in the way to form dimers as shown in Fig.2. These dimers are further connected through O—H···O hydrogen bonds building infinite one-dimensional chains parallel to [0 1 0] direction (Table 1).