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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m553.
Published online 2009 April 22. doi:  10.1107/S1600536809014202
PMCID: PMC2977600

8-Hydr­oxy-2-methyl­quinolinium dichlorido(2-methyl­quinolin-8-olato-κ2 N,O)zincate(II) methanol solvate

Abstract

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

Unlike 8-hydroxy­quinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxy­quinoline forms only a small number of metal chelates. Besides a related acetate salt (Sattarzadeh et al., 2009 [triangle]), there is only one crystal structure report of another zinc derivative; for aqua­bis(2-methyl­quinolin-8-ato)zinc, see: da Silva et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m553-scheme1.jpg

Experimental

Crystal data

  • (C10H10NO)[ZnCl2(C10H8NO)]·CH4O
  • M r = 486.68
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m553-efi1.jpg
  • a = 10.0717 (2) Å
  • b = 13.7886 (3) Å
  • c = 15.4828 (3) Å
  • β = 105.48 (1)°
  • V = 2072.15 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.47 mm−1
  • T = 100 K
  • 0.32 × 0.12 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.651, T max = 0.892
  • 18982 measured reflections
  • 4753 independent reflections
  • 3600 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.108
  • S = 1.02
  • 4753 reflections
  • 277 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.08 e Å−3
  • Δρmin = −1.00 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014202/tk2423sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014202/tk2423Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

(C10H10NO)[ZnCl2(C10H8NO)]·CH4OF(000) = 1000
Mr = 486.68Dx = 1.560 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer4753 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

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 = 1.02w = 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 Å3
3 restraintsΔρmin = −1.00 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2423).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m554. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography