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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1276.
Published online 2010 September 18. doi:  10.1107/S1600536810036706
PMCID: PMC2983420

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

Abstract

The anion of the title salt, (C10H10NO)[ZnBr2(C10H8NO)]·CH3OH, has its metal atom N,O-chelated by the deprotonated 2-methyl-8-hy­droxy­quinoline ligand. The hy­droxy unit of the cation is a hydrogen-bond donor to the alkoxide O atom of the tetra­hedrally coordinated anion, whereas the ammonium cation is a hydrogen-bond donor to the methano­lic O atom. In the crystal, adjacent ion pairs and solvent mol­ecules are linked by a methanol–halogen O—H(...)Br hydrogen bond, generating a chain running along the a axis.

Related literature

For the isostructural chloro analog, see: Sattarzadeh et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1276-scheme1.jpg

Experimental

Crystal data

  • (C10H10NO)[ZnBr2(C10H8NO)]·CH4O
  • M r = 575.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1276-efi1.jpg
  • a = 9.9704 (8) Å
  • b = 13.9954 (11) Å
  • c = 15.8815 (12) Å
  • β = 105.815 (1)°
  • V = 2132.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.93 mm−1
  • T = 100 K
  • 0.35 × 0.30 × 0.25 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.278, T max = 0.372
  • 19908 measured reflections
  • 4889 independent reflections
  • 4044 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.057
  • S = 1.03
  • 4889 reflections
  • 267 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036706/bt5354sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036706/bt5354Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

An earlier study reported C10H10NO+.ZnCI2(C10H8NO).CH3OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Cl hydrogen bonds into a linear chain (Sattarzadeh et al., 2009). The present bromide analog (Scheme I, Fig. 1) is isostructural, the two compounds displaying matching cell dimensions. The hydroxy unit of the cation is hydrogen-bond donor to the alkoxide O atom of the tetrahedrally coordinated anion whereas the ammonium unit is hydrogen-bond donor to the methanolic O atom. Adjacent ion-pairs and solvent molecules are linked by a O–Hmethanol···Br hydrogen bond to generate a linear chain running along the a-axis of the monoclinic unit cell.

Experimental

Zinc bromide (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

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98, N–H 0.86 and O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,N,O).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C10H10NO)[ZnBr2(C10H8NO)]·CH4OF(000) = 1144
Mr = 575.60Dx = 1.793 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6099 reflections
a = 9.9704 (8) Åθ = 2.6–28.2°
b = 13.9954 (11) ŵ = 4.93 mm1
c = 15.8815 (12) ÅT = 100 K
β = 105.815 (1)°Prism, yellow
V = 2132.2 (3) Å30.35 × 0.30 × 0.25 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4889 independent reflections
Radiation source: fine-focus sealed tube4044 reflections with I > 2σ(I)
graphiteRint = 0.040
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.278, Tmax = 0.372k = −18→18
19908 measured reflectionsl = −19→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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0224P)2 + 0.8543P] where P = (Fo2 + 2Fc2)/3
4889 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
Br11.00294 (2)0.228905 (17)0.184698 (15)0.01708 (6)
Br21.12097 (3)0.497149 (17)0.227454 (16)0.02018 (7)
Zn10.99449 (3)0.369708 (19)0.266658 (17)0.01403 (7)
O10.79813 (16)0.40171 (12)0.25997 (10)0.0166 (4)
O20.58392 (16)0.36051 (12)0.13590 (10)0.0155 (3)
H20.65900.37180.17410.023*
O30.30839 (18)0.27619 (14)0.15184 (11)0.0255 (4)
H30.22400.26600.14820.038*
N11.01652 (19)0.36488 (13)0.39831 (12)0.0120 (4)
N20.35285 (19)0.35026 (13)0.00209 (12)0.0129 (4)
H2N0.35400.33480.05470.015*
C10.8930 (2)0.38963 (15)0.41453 (15)0.0124 (5)
C20.7784 (2)0.40932 (16)0.33955 (15)0.0141 (5)
C30.6537 (2)0.43641 (17)0.35416 (16)0.0168 (5)
H3a0.57620.45050.30580.020*
C40.6399 (3)0.44345 (17)0.43988 (16)0.0181 (5)
H40.55250.46190.44800.022*
C50.7483 (3)0.42455 (17)0.51175 (16)0.0185 (5)
H50.73620.42950.56890.022*
C60.8786 (2)0.39750 (16)0.50003 (15)0.0143 (5)
C70.9995 (3)0.37848 (16)0.56932 (15)0.0169 (5)
H70.99520.38260.62830.020*
C81.1213 (3)0.35443 (16)0.55191 (15)0.0157 (5)
H81.20160.34150.59870.019*
C91.1288 (2)0.34858 (15)0.46464 (15)0.0140 (5)
C101.2609 (2)0.32358 (17)0.44237 (16)0.0177 (5)
H10A1.29130.37810.41350.027*
H10B1.24470.26830.40300.027*
H10C1.33320.30790.49610.027*
C110.4758 (2)0.37589 (15)−0.01425 (15)0.0124 (5)
C120.5986 (2)0.38162 (15)0.05651 (15)0.0127 (5)
C130.7208 (2)0.40884 (16)0.03862 (15)0.0144 (5)
H130.80440.41290.08470.017*
C140.7223 (2)0.43073 (16)−0.04781 (16)0.0157 (5)
H140.80760.4494−0.05880.019*
C150.6052 (2)0.42585 (16)−0.11591 (15)0.0157 (5)
H150.60900.4413−0.17350.019*
C160.4782 (2)0.39768 (15)−0.10042 (15)0.0133 (5)
C170.3494 (2)0.39320 (16)−0.16628 (16)0.0164 (5)
H170.34700.4067−0.22530.020*
C180.2294 (3)0.36989 (16)−0.14609 (16)0.0178 (5)
H180.14380.3684−0.19080.021*
C190.2312 (2)0.34802 (16)−0.05948 (15)0.0152 (5)
C200.1026 (2)0.32331 (18)−0.03312 (17)0.0212 (5)
H20A0.10080.35980.01920.032*
H20B0.10250.2548−0.02040.032*
H20C0.02020.3392−0.08090.032*
C210.3867 (3)0.27543 (19)0.24135 (16)0.0218 (5)
H21A0.48640.27420.24520.033*
H21B0.36230.21860.27010.033*
H21C0.36520.33290.27040.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.01686 (12)0.02067 (12)0.01393 (12)−0.00406 (9)0.00458 (9)−0.00180 (9)
Br20.02141 (13)0.02021 (12)0.02170 (14)−0.00056 (10)0.01060 (11)0.00474 (10)
Zn10.01209 (14)0.02082 (14)0.00922 (14)−0.00032 (11)0.00298 (10)0.00126 (11)
O10.0102 (8)0.0304 (9)0.0080 (8)0.0014 (7)0.0003 (6)0.0007 (7)
O20.0124 (8)0.0244 (9)0.0078 (8)−0.0009 (7)−0.0005 (6)0.0012 (7)
O30.0159 (9)0.0454 (12)0.0159 (9)−0.0032 (9)0.0056 (7)0.0036 (8)
N10.0126 (9)0.0126 (9)0.0103 (9)−0.0021 (8)0.0024 (8)0.0006 (7)
N20.0143 (10)0.0131 (9)0.0103 (10)0.0007 (8)0.0019 (8)0.0002 (7)
C10.0154 (12)0.0108 (10)0.0119 (11)−0.0042 (9)0.0051 (9)−0.0005 (8)
C20.0157 (12)0.0144 (11)0.0119 (12)−0.0035 (9)0.0032 (9)0.0000 (9)
C30.0130 (11)0.0203 (12)0.0154 (12)−0.0033 (9)0.0011 (10)0.0006 (9)
C40.0150 (12)0.0197 (12)0.0217 (13)−0.0031 (10)0.0084 (10)−0.0042 (10)
C50.0270 (14)0.0165 (12)0.0152 (12)−0.0053 (10)0.0113 (11)−0.0031 (10)
C60.0189 (12)0.0124 (11)0.0116 (11)−0.0042 (9)0.0043 (10)0.0006 (9)
C70.0262 (13)0.0152 (12)0.0090 (12)−0.0049 (10)0.0045 (10)−0.0006 (9)
C80.0197 (12)0.0131 (11)0.0120 (12)−0.0016 (9)0.0003 (10)0.0007 (9)
C90.0177 (12)0.0097 (11)0.0144 (12)−0.0032 (9)0.0039 (10)0.0010 (9)
C100.0158 (12)0.0202 (12)0.0153 (13)0.0008 (10)0.0013 (10)0.0005 (10)
C110.0160 (12)0.0095 (10)0.0118 (11)0.0033 (9)0.0041 (9)−0.0007 (8)
C120.0153 (11)0.0120 (11)0.0100 (11)0.0022 (9)0.0018 (9)−0.0016 (8)
C130.0114 (11)0.0165 (11)0.0140 (12)0.0022 (9)0.0012 (9)−0.0018 (9)
C140.0142 (12)0.0155 (11)0.0199 (13)0.0023 (9)0.0090 (10)−0.0004 (9)
C150.0212 (13)0.0161 (11)0.0112 (12)0.0023 (10)0.0065 (10)−0.0001 (9)
C160.0168 (12)0.0108 (10)0.0115 (11)0.0049 (9)0.0021 (9)−0.0008 (9)
C170.0217 (13)0.0139 (11)0.0134 (12)0.0052 (9)0.0042 (10)−0.0012 (9)
C180.0175 (12)0.0186 (12)0.0144 (12)0.0021 (10)−0.0009 (10)−0.0022 (9)
C190.0152 (12)0.0114 (11)0.0175 (13)0.0007 (9)0.0017 (10)−0.0005 (9)
C200.0145 (12)0.0254 (13)0.0220 (14)−0.0006 (10)0.0023 (11)0.0035 (11)
C210.0207 (13)0.0275 (14)0.0160 (13)−0.0011 (11)0.0032 (10)0.0022 (10)

Geometric parameters (Å, °)

Br1—Zn12.3758 (4)C8—H80.9500
Br2—Zn12.3637 (4)C9—C101.496 (3)
Zn1—O11.9828 (16)C10—H10A0.9800
Zn1—N12.0431 (19)C10—H10B0.9800
O1—C21.335 (3)C10—H10C0.9800
O2—C121.341 (3)C11—C161.409 (3)
O2—H20.8400C11—C121.421 (3)
O3—C211.423 (3)C12—C131.378 (3)
O3—H30.8400C13—C141.411 (3)
N1—C91.331 (3)C13—H130.9500
N1—C11.370 (3)C14—C151.359 (3)
N2—C191.335 (3)C14—H140.9500
N2—C111.368 (3)C15—C161.411 (3)
N2—H2N0.8600C15—H150.9500
C1—C61.408 (3)C16—C171.419 (3)
C1—C21.434 (3)C17—C181.360 (3)
C2—C31.379 (3)C17—H170.9500
C3—C41.409 (3)C18—C191.404 (3)
C3—H3a0.9500C18—H180.9500
C4—C51.367 (3)C19—C201.494 (3)
C4—H40.9500C20—H20A0.9800
C5—C61.414 (3)C20—H20B0.9800
C5—H50.9500C20—H20C0.9800
C6—C71.418 (3)C21—H21A0.9800
C7—C81.359 (3)C21—H21B0.9800
C7—H70.9500C21—H21C0.9800
C8—C91.411 (3)
O1—Zn1—N183.77 (7)H10A—C10—H10B109.5
O1—Zn1—Br2113.91 (5)C9—C10—H10C109.5
N1—Zn1—Br2112.22 (5)H10A—C10—H10C109.5
O1—Zn1—Br1109.87 (5)H10B—C10—H10C109.5
N1—Zn1—Br1121.55 (5)N2—C11—C16119.6 (2)
Br2—Zn1—Br1112.362 (14)N2—C11—C12119.2 (2)
C2—O1—Zn1111.41 (13)C16—C11—C12121.1 (2)
C12—O2—H2109.5O2—C12—C13125.7 (2)
C21—O3—H3109.5O2—C12—C11116.1 (2)
C9—N1—C1119.98 (19)C13—C12—C11118.2 (2)
C9—N1—Zn1130.41 (16)C12—C13—C14120.4 (2)
C1—N1—Zn1109.43 (14)C12—C13—H13119.8
C19—N2—C11123.3 (2)C14—C13—H13119.8
C19—N2—H2N118.3C15—C14—C13121.9 (2)
C11—N2—H2N118.3C15—C14—H14119.0
N1—C1—C6122.3 (2)C13—C14—H14119.0
N1—C1—C2116.5 (2)C14—C15—C16119.5 (2)
C6—C1—C2121.2 (2)C14—C15—H15120.3
O1—C2—C3123.6 (2)C16—C15—H15120.3
O1—C2—C1118.8 (2)C11—C16—C15118.9 (2)
C3—C2—C1117.6 (2)C11—C16—C17117.1 (2)
C2—C3—C4120.8 (2)C15—C16—C17124.0 (2)
C2—C3—H3a119.6C18—C17—C16120.9 (2)
C4—C3—H3a119.6C18—C17—H17119.5
C5—C4—C3122.0 (2)C16—C17—H17119.5
C5—C4—H4119.0C17—C18—C19120.4 (2)
C3—C4—H4119.0C17—C18—H18119.8
C4—C5—C6119.2 (2)C19—C18—H18119.8
C4—C5—H5120.4N2—C19—C18118.6 (2)
C6—C5—H5120.4N2—C19—C20118.6 (2)
C1—C6—C5119.1 (2)C18—C19—C20122.8 (2)
C1—C6—C7116.5 (2)C19—C20—H20A109.5
C5—C6—C7124.4 (2)C19—C20—H20B109.5
C8—C7—C6120.4 (2)H20A—C20—H20B109.5
C8—C7—H7119.8C19—C20—H20C109.5
C6—C7—H7119.8H20A—C20—H20C109.5
C7—C8—C9120.3 (2)H20B—C20—H20C109.5
C7—C8—H8119.9O3—C21—H21A109.5
C9—C8—H8119.9O3—C21—H21B109.5
N1—C9—C8120.6 (2)H21A—C21—H21B109.5
N1—C9—C10117.2 (2)O3—C21—H21C109.5
C8—C9—C10122.1 (2)H21A—C21—H21C109.5
C9—C10—H10A109.5H21B—C21—H21C109.5
C9—C10—H10B109.5
N1—Zn1—O1—C23.23 (14)C6—C7—C8—C90.3 (3)
Br2—Zn1—O1—C2−108.35 (14)C1—N1—C9—C81.4 (3)
Br1—Zn1—O1—C2124.58 (13)Zn1—N1—C9—C8176.10 (15)
O1—Zn1—N1—C9−178.0 (2)C1—N1—C9—C10−178.93 (19)
Br2—Zn1—N1—C9−64.7 (2)Zn1—N1—C9—C10−4.3 (3)
Br1—Zn1—N1—C972.5 (2)C7—C8—C9—N1−1.1 (3)
O1—Zn1—N1—C1−2.90 (14)C7—C8—C9—C10179.2 (2)
Br2—Zn1—N1—C1110.42 (13)C19—N2—C11—C16−2.7 (3)
Br1—Zn1—N1—C1−112.43 (13)C19—N2—C11—C12176.3 (2)
C9—N1—C1—C6−0.9 (3)N2—C11—C12—O20.2 (3)
Zn1—N1—C1—C6−176.60 (17)C16—C11—C12—O2179.15 (19)
C9—N1—C1—C2177.82 (19)N2—C11—C12—C13−179.13 (19)
Zn1—N1—C1—C22.1 (2)C16—C11—C12—C13−0.2 (3)
Zn1—O1—C2—C3176.09 (18)O2—C12—C13—C14−179.0 (2)
Zn1—O1—C2—C1−3.1 (2)C11—C12—C13—C140.3 (3)
N1—C1—C2—O10.6 (3)C12—C13—C14—C15−0.1 (3)
C6—C1—C2—O1179.3 (2)C13—C14—C15—C16−0.3 (3)
N1—C1—C2—C3−178.6 (2)N2—C11—C16—C15178.7 (2)
C6—C1—C2—C30.1 (3)C12—C11—C16—C15−0.2 (3)
O1—C2—C3—C4−179.7 (2)N2—C11—C16—C171.1 (3)
C1—C2—C3—C4−0.6 (3)C12—C11—C16—C17−177.8 (2)
C2—C3—C4—C50.4 (4)C14—C15—C16—C110.4 (3)
C3—C4—C5—C60.3 (4)C14—C15—C16—C17177.9 (2)
N1—C1—C6—C5179.2 (2)C11—C16—C17—C180.8 (3)
C2—C1—C6—C50.6 (3)C15—C16—C17—C18−176.8 (2)
N1—C1—C6—C70.1 (3)C16—C17—C18—C19−1.2 (3)
C2—C1—C6—C7−178.6 (2)C11—N2—C19—C182.2 (3)
C4—C5—C6—C1−0.7 (3)C11—N2—C19—C20−177.2 (2)
C4—C5—C6—C7178.4 (2)C17—C18—C19—N2−0.3 (3)
C1—C6—C7—C80.2 (3)C17—C18—C19—C20179.1 (2)
C5—C6—C7—C8−178.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O10.841.712.546 (2)172
O3—H3···Br1i0.842.483.2941 (17)163
N2—H2n···O30.861.912.739 (3)162

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5354).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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