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Acta Cryst. (2009). E65, m553    [ doi:10.1107/S1600536809014202 ]

8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-[kappa]2N,O)zincate(II) methanol solvate

E. Sattarzadeh, G. Mohammadnezhad, M. M. Amini and S. W. Ng

Abstract top

The reaction of zinc chloride and 2-methyl-8-hydroxyquinoline in methanol yielded the title monosolvated salt, (C10H10NO)[ZnCl2(C10H8NO)]·CH3OH, which has the Zn atom within a distorted Cl2NO tetrahedral coordination geometry. Supramolecular chains feature in the crystal structure, comprising all components of the structure stabilized by a combination of O-H...O, N-H...O and O-H...Cl hydrogen bonding.

Related literature top

Unlike 8-hydroxyquinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxyquinoline forms only a small number of metal chelates. There is only one crystal structure report of a zinc derivative; for aquabis(2-methylquinolin-8-ato)zinc, see: da Silva et al. (2007).

Experimental top

Zinc chloride (0.10 g, 0.75 mmol) and 2-methyl-8-hydroxyquinoline (0.24 g, 1.5 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after several days.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The O–H and N–H hydrogen atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and N–H 0.88±01 Å; their temperature factors were freely refined.

The final difference Fourier map had a large peak/deep hole in the vicinity of the O3 atom.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C10H10NO][Zn(C10H8NO)Cl2].CH3OH; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius.
8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ2N,O)zincate(II) methanol solvate top
Crystal data top
(C10H10NO)[ZnCl2(C10H8NO)]·CH4OF(000) = 1000
Mr = 486.68Dx = 1.560 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4908 reflections
a = 10.0717 (2) Åθ = 2.6–27.1°
b = 13.7886 (3) ŵ = 1.47 mm−1
c = 15.4828 (3) ÅT = 100 K
β = 105.48 (1)°Block, yellow
V = 2072.15 (7) Å30.32 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		4753 independent reflections
Radiation source: fine-focus sealed tube3600 reflections with I > 2σ(I)
graphiteRint = 0.036
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.651, Tmax = 0.892k = −17→17
18982 measured reflectionsl = −20→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0493P)2 + 2.8684P]
where P = (Fo2 + 2Fc2)/3
4753 reflections(Δ/σ)max = 0.001
277 parametersΔρmax = 1.08 e Å−3
3 restraintsΔρmin = −1.00 e Å−3
Crystal data top
(C10H10NO)[ZnCl2(C10H8NO)]·CH4OV = 2072.15 (7) Å3
Mr = 486.68Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0717 (2) ŵ = 1.47 mm−1
b = 13.7886 (3) ÅT = 100 K
c = 15.4828 (3) Å0.32 × 0.12 × 0.08 mm
β = 105.48 (1)°
Data collection top
Bruker SMART APEX
diffractometer		4753 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3600 reflections with I > 2σ(I)
Tmin = 0.651, Tmax = 0.892Rint = 0.036
18982 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108Δρmax = 1.08 e Å−3
S = 1.02Δρmin = −1.00 e Å−3
4753 reflectionsAbsolute structure: ?
277 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50382 (3)0.63261 (3)0.23689 (2)0.02655 (11)
Cl10.48941 (8)0.76378 (6)0.31836 (5)0.03149 (18)
Cl20.39683 (8)0.50528 (6)0.27699 (5)0.03503 (19)
O10.6980 (2)0.60686 (17)0.23887 (13)0.0318 (5)
O20.9135 (2)0.63848 (15)0.36428 (13)0.0258 (4)
H2O0.843 (3)0.626 (3)0.3225 (19)0.054 (13)*
O31.1916 (3)0.6985 (4)0.3410 (2)0.1114 (18)
H3O1.2770 (14)0.706 (5)0.353 (4)0.11 (2)*
N10.4760 (2)0.63643 (17)0.10133 (15)0.0232 (5)
N21.1439 (2)0.64419 (17)0.49938 (16)0.0239 (5)
H2N1.143 (4)0.657 (3)0.4435 (10)0.040 (10)*
C10.7143 (3)0.6004 (2)0.15652 (19)0.0257 (6)
C20.8383 (3)0.5781 (2)0.1389 (2)0.0345 (7)
H20.91780.56760.18720.041*
C30.8481 (3)0.5708 (2)0.0502 (2)0.0363 (8)
H30.93470.55570.04010.044*
C40.7372 (4)0.5847 (2)−0.0217 (2)0.0344 (7)
H40.74660.5793−0.08100.041*
C50.6079 (3)0.6075 (2)−0.00683 (19)0.0280 (6)
C60.5975 (3)0.6156 (2)0.08206 (18)0.0238 (6)
C70.4857 (4)0.6220 (2)−0.0757 (2)0.0324 (7)
H70.48730.6172−0.13660.039*
C80.3656 (3)0.6428 (2)−0.05527 (19)0.0303 (7)
H80.28390.6530−0.10200.036*
C90.3619 (3)0.6491 (2)0.03512 (19)0.0259 (6)
C100.2318 (3)0.6695 (2)0.0599 (2)0.0322 (7)
H10A0.24450.72640.09920.048*
H10B0.20740.61340.09140.048*
H10C0.15770.68230.00560.048*
C110.8990 (3)0.61926 (19)0.44627 (18)0.0211 (5)
C120.7783 (3)0.5956 (2)0.46570 (19)0.0254 (6)
H120.69530.59260.41890.031*
C130.7759 (3)0.5758 (2)0.5544 (2)0.0267 (6)
H130.69090.55940.56640.032*
C140.8927 (3)0.5795 (2)0.62372 (19)0.0279 (6)
H140.88870.56570.68310.033*
C151.0188 (3)0.6040 (2)0.60665 (18)0.0241 (6)
C161.0214 (3)0.62310 (19)0.51737 (18)0.0218 (6)
C171.1463 (3)0.6076 (2)0.6733 (2)0.0300 (7)
H171.14880.59610.73420.036*
C181.2650 (3)0.6276 (2)0.6509 (2)0.0309 (7)
H181.34960.62930.69640.037*
C191.2646 (3)0.6457 (2)0.5617 (2)0.0284 (6)
C201.3919 (3)0.6644 (3)0.5335 (2)0.0381 (8)
H20A1.39320.62270.48250.057*
H20B1.47260.65040.58340.057*
H20C1.39400.73260.51580.057*
C211.1182 (4)0.7302 (3)0.2615 (2)0.0478 (9)
H21C1.15770.79110.24710.072*
H21B1.02280.74130.26320.072*
H21A1.12000.68170.21560.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02484 (18)0.0370 (2)0.01749 (17)−0.00010 (14)0.00511 (13)0.00387 (14)
Cl10.0333 (4)0.0367 (4)0.0238 (3)−0.0047 (3)0.0066 (3)−0.0003 (3)
Cl20.0401 (4)0.0349 (4)0.0342 (4)−0.0009 (3)0.0170 (3)0.0076 (3)
O10.0251 (11)0.0528 (14)0.0170 (10)−0.0012 (10)0.0047 (8)0.0001 (9)
O20.0260 (10)0.0327 (11)0.0173 (10)−0.0003 (9)0.0032 (8)0.0002 (8)
O30.0368 (18)0.240 (5)0.063 (2)0.040 (2)0.0233 (16)0.091 (3)
N10.0269 (12)0.0231 (12)0.0180 (11)−0.0054 (10)0.0029 (9)0.0023 (9)
N20.0252 (12)0.0233 (12)0.0219 (12)0.0037 (10)0.0037 (10)0.0026 (10)
C10.0268 (15)0.0291 (15)0.0212 (14)−0.0070 (12)0.0063 (11)−0.0022 (11)
C20.0294 (16)0.0411 (19)0.0340 (17)−0.0086 (14)0.0100 (13)−0.0070 (14)
C30.0348 (18)0.0404 (19)0.0404 (19)−0.0108 (14)0.0216 (15)−0.0121 (15)
C40.048 (2)0.0317 (17)0.0290 (16)−0.0104 (15)0.0197 (15)−0.0057 (13)
C50.0413 (17)0.0217 (14)0.0222 (14)−0.0087 (12)0.0108 (13)0.0003 (11)
C60.0286 (15)0.0237 (14)0.0189 (13)−0.0073 (11)0.0062 (11)−0.0001 (10)
C70.053 (2)0.0247 (15)0.0175 (14)−0.0061 (14)0.0055 (13)−0.0002 (11)
C80.0424 (18)0.0250 (15)0.0162 (13)−0.0023 (13)−0.0050 (12)0.0019 (11)
C90.0306 (15)0.0206 (14)0.0230 (14)−0.0036 (11)0.0009 (12)0.0017 (11)
C100.0299 (16)0.0333 (16)0.0288 (16)0.0019 (13)−0.0001 (13)0.0029 (13)
C110.0276 (14)0.0176 (13)0.0170 (12)0.0024 (11)0.0041 (11)0.0006 (10)
C120.0271 (15)0.0254 (14)0.0227 (14)0.0006 (11)0.0048 (12)−0.0022 (11)
C130.0295 (15)0.0253 (15)0.0281 (15)0.0009 (12)0.0123 (12)0.0011 (12)
C140.0379 (17)0.0252 (15)0.0210 (14)0.0042 (13)0.0086 (12)0.0017 (11)
C150.0306 (15)0.0196 (13)0.0209 (14)0.0044 (11)0.0049 (11)−0.0026 (11)
C160.0266 (14)0.0181 (13)0.0199 (13)0.0033 (11)0.0047 (11)−0.0005 (10)
C170.0380 (17)0.0286 (16)0.0198 (14)0.0054 (13)0.0016 (12)−0.0013 (12)
C180.0282 (15)0.0321 (16)0.0260 (15)0.0031 (13)−0.0040 (12)−0.0026 (12)
C190.0274 (15)0.0230 (15)0.0307 (16)0.0033 (12)0.0005 (12)0.0000 (12)
C200.0264 (16)0.0411 (19)0.043 (2)−0.0007 (14)0.0029 (14)0.0084 (15)
C210.048 (2)0.057 (2)0.040 (2)−0.0010 (18)0.0137 (17)0.0023 (18)
Geometric parameters (Å, °) top
Zn1—N12.043 (2)C8—H80.9500
Zn1—O11.980 (2)C9—C101.488 (4)
Zn1—Cl12.2318 (8)C10—H10A0.9800
Zn1—Cl22.2331 (8)C10—H10B0.9800
O1—C11.331 (3)C10—H10C0.9800
O2—C111.342 (3)C11—C121.368 (4)
O2—H2O0.841 (10)C11—C161.418 (4)
O3—C211.329 (5)C12—C131.407 (4)
O3—H3O0.836 (10)C12—H120.9500
N1—C91.332 (4)C13—C141.365 (4)
N1—C61.365 (4)C13—H130.9500
N2—C191.335 (4)C14—C151.406 (4)
N2—C161.367 (4)C14—H140.9500
N2—H2N0.881 (10)C15—C161.414 (4)
C1—C21.382 (4)C15—C171.417 (4)
C1—C61.426 (4)C17—C181.359 (5)
C2—C31.406 (4)C17—H170.9500
C2—H20.9500C18—C191.402 (4)
C3—C41.364 (5)C18—H180.9500
C3—H30.9500C19—C201.484 (4)
C4—C51.417 (5)C20—H20A0.9800
C4—H40.9500C20—H20B0.9800
C5—C71.411 (4)C20—H20C0.9800
C5—C61.412 (4)C21—H21C0.9800
C7—C81.360 (5)C21—H21B0.9800
C7—H70.9500C21—H21A0.9800
C8—C91.413 (4)
O1—Zn1—N183.36 (9)H10A—C10—H10B109.5
O1—Zn1—Cl1110.46 (7)C9—C10—H10C109.5
N1—Zn1—Cl1123.24 (7)H10A—C10—H10C109.5
O1—Zn1—Cl2113.75 (7)H10B—C10—H10C109.5
N1—Zn1—Cl2111.22 (7)O2—C11—C12125.6 (3)
Cl1—Zn1—Cl2111.78 (3)O2—C11—C16115.8 (2)
C1—O1—Zn1111.79 (18)C12—C11—C16118.5 (3)
C11—O2—H2O114 (3)C11—C12—C13120.6 (3)
C21—O3—H3O117 (4)C11—C12—H12119.7
C9—N1—C6119.9 (2)C13—C12—H12119.7
C9—N1—Zn1130.4 (2)C14—C13—C12121.6 (3)
C6—N1—Zn1109.52 (18)C14—C13—H13119.2
C19—N2—C16123.6 (3)C12—C13—H13119.2
C19—N2—H2N118 (2)C13—C14—C15119.6 (3)
C16—N2—H2N118 (2)C13—C14—H14120.2
O1—C1—C2123.6 (3)C15—C14—H14120.2
O1—C1—C6118.6 (3)C14—C15—C16118.8 (3)
C2—C1—C6117.8 (3)C14—C15—C17124.1 (3)
C1—C2—C3120.7 (3)C16—C15—C17117.0 (3)
C1—C2—H2119.6N2—C16—C15119.5 (3)
C3—C2—H2119.6N2—C16—C11119.7 (2)
C4—C3—C2122.2 (3)C15—C16—C11120.9 (3)
C4—C3—H3118.9C18—C17—C15120.7 (3)
C2—C3—H3118.9C18—C17—H17119.7
C3—C4—C5119.0 (3)C15—C17—H17119.7
C3—C4—H4120.5C17—C18—C19121.0 (3)
C5—C4—H4120.5C17—C18—H18119.5
C7—C5—C6116.7 (3)C19—C18—H18119.5
C7—C5—C4124.2 (3)N2—C19—C18118.1 (3)
C6—C5—C4119.1 (3)N2—C19—C20118.8 (3)
N1—C6—C5122.2 (3)C18—C19—C20123.0 (3)
N1—C6—C1116.6 (2)C19—C20—H20A109.5
C5—C6—C1121.1 (3)C19—C20—H20B109.5
C8—C7—C5120.3 (3)H20A—C20—H20B109.5
C8—C7—H7119.8C19—C20—H20C109.5
C5—C7—H7119.8H20A—C20—H20C109.5
C7—C8—C9120.2 (3)H20B—C20—H20C109.5
C7—C8—H8119.9O3—C21—H21C109.5
C9—C8—H8119.9O3—C21—H21B109.5
N1—C9—C8120.6 (3)H21C—C21—H21B109.5
N1—C9—C10117.7 (3)O3—C21—H21A109.5
C8—C9—C10121.7 (3)H21C—C21—H21A109.5
C9—C10—H10A109.5H21B—C21—H21A109.5
C9—C10—H10B109.5
N1—Zn1—O1—C1−2.8 (2)C5—C7—C8—C9−0.5 (4)
Cl1—Zn1—O1—C1−125.81 (18)C6—N1—C9—C8−1.0 (4)
Cl2—Zn1—O1—C1107.55 (19)Zn1—N1—C9—C8−175.8 (2)
O1—Zn1—N1—C9178.1 (3)C6—N1—C9—C10178.7 (3)
Cl1—Zn1—N1—C9−71.7 (3)Zn1—N1—C9—C103.8 (4)
Cl2—Zn1—N1—C965.2 (3)C7—C8—C9—N11.0 (4)
O1—Zn1—N1—C62.88 (18)C7—C8—C9—C10−178.6 (3)
Cl1—Zn1—N1—C6113.03 (17)O2—C11—C12—C13179.2 (3)
Cl2—Zn1—N1—C6−110.05 (17)C16—C11—C12—C130.1 (4)
Zn1—O1—C1—C2−176.7 (3)C11—C12—C13—C140.1 (4)
Zn1—O1—C1—C62.2 (3)C12—C13—C14—C150.1 (4)
O1—C1—C2—C3178.9 (3)C13—C14—C15—C16−0.7 (4)
C6—C1—C2—C30.1 (5)C13—C14—C15—C17−178.4 (3)
C1—C2—C3—C4−0.3 (5)C19—N2—C16—C151.7 (4)
C2—C3—C4—C50.1 (5)C19—N2—C16—C11−177.4 (3)
C3—C4—C5—C7−179.0 (3)C14—C15—C16—N2−178.1 (3)
C3—C4—C5—C60.3 (4)C17—C15—C16—N2−0.2 (4)
C9—N1—C6—C50.5 (4)C14—C15—C16—C110.9 (4)
Zn1—N1—C6—C5176.3 (2)C17—C15—C16—C11178.9 (2)
C9—N1—C6—C1−178.4 (3)O2—C11—C16—N2−0.8 (4)
Zn1—N1—C6—C1−2.6 (3)C12—C11—C16—N2178.4 (2)
C7—C5—C6—N1−0.1 (4)O2—C11—C16—C15−179.9 (2)
C4—C5—C6—N1−179.4 (3)C12—C11—C16—C15−0.7 (4)
C7—C5—C6—C1178.8 (3)C14—C15—C17—C18177.0 (3)
C4—C5—C6—C1−0.6 (4)C16—C15—C17—C18−0.8 (4)
O1—C1—C6—N10.4 (4)C15—C17—C18—C190.5 (5)
C2—C1—C6—N1179.3 (3)C16—N2—C19—C18−2.0 (4)
O1—C1—C6—C5−178.6 (3)C16—N2—C19—C20176.8 (3)
C2—C1—C6—C50.4 (4)C17—C18—C19—N20.9 (4)
C6—C5—C7—C80.1 (4)C17—C18—C19—C20−177.8 (3)
C4—C5—C7—C8179.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.84 (1)1.70 (1)2.534 (3)177 (4)
O3—H3O···Cl1i0.84 (1)2.47 (3)3.239 (4)153 (5)
N2—H2N···O30.88 (1)1.87 (2)2.727 (4)163 (3)
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.84 (1)1.70 (1)2.534 (3)177 (4)
O3—H3O···Cl1i0.84 (1)2.47 (3)3.239 (4)153 (5)
N2—H2N···O30.88 (1)1.87 (2)2.727 (4)163 (3)
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Silva, L. E. da, Joussef, A. C., Rebelo, R. A., Foro, S. & Schmidt, B. (2007). Acta Cryst. E63, m129–m131.

Westrip, S. P. (2009). publCIF. In preparation.