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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1278.
Published online 2010 September 18. doi:  10.1107/S160053681003672X
PMCID: PMC2983236

Bromido(quinolin-8-ol-κ2 N,O)(quinolin-8-olato-κ2 N,O)zinc(II) methanol monosolvate

Abstract

The title compound, [ZnBr(C9H6NO)(C9H7NO)]·CH3OH, has its metal atom N,O-chelated by a neutral and a deproton­ated 8-hy­droxy­quinoline ligand. The hy­droxy unit of the neutral ligand is a hydrogen-bond donor to the methanol O atom and the alk­oxy O atom of the monoanionic ligand is a hydrogen-bond acceptor to the methanol O atom. In the crystal, adjacent mol­ecules are linked by these two hydrogen bonds, generating a chain running along the a axis.

Related literature

For a related structure, see: Najafi et al. (2010 [triangle]).

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Object name is e-66-m1278-scheme1.jpg

Experimental

Crystal data

  • [ZnBr(C9H6NO)(C9H7NO)]·CH4O
  • M r = 466.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1278-efi1.jpg
  • a = 8.4485 (7) Å
  • b = 8.6968 (7) Å
  • c = 13.1868 (10) Å
  • α = 97.241 (1)°
  • β = 99.209 (1)°
  • γ = 109.470 (1)°
  • V = 884.81 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.67 mm−1
  • T = 100 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.406, T max = 0.711
  • 8392 measured reflections
  • 4022 independent reflections
  • 3354 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.103
  • S = 1.10
  • 4022 reflections
  • 237 parameters
  • H-atom parameters constrained
  • Δρmax = 0.78 e Å−3
  • Δρmin = −0.85 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/S160053681003672X/bt5356sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003672X/bt5356Isup2.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+.ZnBr2(C10H8NO).CH3OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Br hydrogen bonds into a linear chain. The salt was synthesized by reacting zinc bromide and 2-methyl-8-hydroxyquinoline in methanol; no base was added (Najafi et al., 2010). The present study uses 8-hydoxyquinoline instead of 2-methy-8-hydroxyquinoline as the organic reactant. The product is a mono-solavated neutral molecule (Scheme I, Fig. 1). The methanol-solvated compound, ZnBr(C9H6NO)(C9H7NO).CH3OH, has its metal atom N,O-chelated by a neutral and deprotonated 8-hydroxyquinoline ligand. The hydroxy unit of the neutral ligand is hydrogen-bond donor methanol O atom and the alkoxy O atom of the monoanionic ligand is hydrogen-bond acceptor to methanol O atom. Adjacent molecules are linked by these two hydrogen bonds to generate a linear chain running along the a-axis of the triclinic unit cell (Fig. 2).

Experimental

Zinc bromide (0.19 g, 0.75 mmol) and 8-hydroxyquinoline (0.22 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, 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,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.
Fig. 2.
Hydrogen bonded chain structure.

Crystal data

[ZnBr(C9H6NO)(C9H7NO)]·CH4OZ = 2
Mr = 466.63F(000) = 468
Triclinic, P1Dx = 1.751 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4485 (7) ÅCell parameters from 3867 reflections
b = 8.6968 (7) Åθ = 2.5–28.2°
c = 13.1868 (10) ŵ = 3.67 mm1
α = 97.241 (1)°T = 100 K
β = 99.209 (1)°Prism, yellow
γ = 109.470 (1)°0.30 × 0.20 × 0.10 mm
V = 884.81 (12) Å3

Data collection

Bruker SMART APEX diffractometer4022 independent reflections
Radiation source: fine-focus sealed tube3354 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.406, Tmax = 0.711k = −11→11
8392 measured reflectionsl = −15→17

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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0457P)2 + 1.9422P] where P = (Fo2 + 2Fc2)/3
4022 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = −0.85 e Å3

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

xyzUiso*/Ueq
Zn10.45338 (5)0.64466 (5)0.71737 (3)0.01184 (12)
Br10.58054 (4)0.92415 (4)0.81357 (3)0.01654 (11)
O10.6864 (3)0.6465 (3)0.64187 (19)0.0152 (5)
O20.2092 (3)0.5306 (3)0.73396 (19)0.0145 (5)
H20.12300.54610.70240.022*
O30.9908 (3)0.6800 (3)0.7299 (2)0.0209 (6)
H30.89080.67070.70160.031*
N10.3868 (4)0.6687 (4)0.5653 (2)0.0119 (6)
N20.5025 (4)0.4869 (3)0.8093 (2)0.0121 (6)
C10.5180 (4)0.7280 (4)0.5148 (3)0.0110 (6)
C20.6796 (4)0.7212 (4)0.5573 (3)0.0128 (7)
C30.8163 (4)0.7842 (4)0.5120 (3)0.0150 (7)
H3A0.92550.78190.54150.018*
C40.7946 (5)0.8531 (5)0.4209 (3)0.0177 (7)
H40.88970.89500.38920.021*
C50.6384 (4)0.8603 (4)0.3777 (3)0.0151 (7)
H50.62640.90800.31720.018*
C60.4957 (5)0.7963 (4)0.4238 (3)0.0141 (7)
C70.3290 (5)0.7915 (4)0.3821 (3)0.0153 (7)
H70.30850.83500.32080.018*
C80.1969 (5)0.7238 (5)0.4304 (3)0.0173 (7)
H80.08350.71660.40200.021*
C90.2328 (4)0.6652 (4)0.5232 (3)0.0156 (7)
H90.14120.62080.55710.019*
C100.3596 (4)0.4025 (4)0.8429 (3)0.0109 (6)
C110.2035 (4)0.4283 (4)0.8012 (3)0.0138 (7)
C120.0569 (4)0.3427 (4)0.8339 (3)0.0150 (7)
H12−0.04810.35600.80740.018*
C130.0599 (5)0.2365 (5)0.9055 (3)0.0165 (7)
H13−0.04330.18000.92630.020*
C140.2083 (5)0.2119 (4)0.9464 (3)0.0165 (7)
H140.20790.14000.99510.020*
C150.3606 (4)0.2956 (4)0.9146 (3)0.0128 (7)
C160.5206 (5)0.2803 (4)0.9519 (3)0.0145 (7)
H160.52820.20850.99960.017*
C170.6636 (5)0.3682 (4)0.9194 (3)0.0153 (7)
H170.77160.36040.94570.018*
C180.6497 (4)0.4706 (4)0.8467 (3)0.0134 (7)
H180.74940.53010.82350.016*
C191.0704 (5)0.8335 (5)0.8036 (3)0.0271 (9)
H19A1.09330.81070.87430.041*
H19B0.99360.89670.80040.041*
H19C1.17890.89840.78670.041*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0117 (2)0.0145 (2)0.0111 (2)0.00508 (15)0.00377 (15)0.00635 (15)
Br10.0208 (2)0.01368 (17)0.01481 (19)0.00510 (14)0.00314 (14)0.00568 (13)
O10.0162 (12)0.0189 (12)0.0138 (12)0.0078 (10)0.0056 (10)0.0078 (10)
O20.0105 (11)0.0194 (12)0.0163 (13)0.0080 (10)0.0012 (9)0.0076 (10)
O30.0130 (12)0.0228 (13)0.0256 (15)0.0072 (11)−0.0002 (11)0.0035 (11)
N10.0106 (13)0.0158 (14)0.0101 (14)0.0054 (11)0.0026 (11)0.0030 (11)
N20.0159 (14)0.0129 (13)0.0080 (13)0.0037 (11)0.0045 (11)0.0049 (11)
C10.0104 (15)0.0115 (15)0.0109 (16)0.0041 (12)0.0033 (12)−0.0001 (12)
C20.0159 (17)0.0138 (15)0.0117 (16)0.0083 (13)0.0044 (13)0.0042 (13)
C30.0115 (16)0.0187 (17)0.0171 (18)0.0080 (13)0.0034 (13)0.0043 (14)
C40.0172 (18)0.0193 (17)0.0155 (18)0.0026 (14)0.0076 (14)0.0052 (14)
C50.0169 (17)0.0161 (16)0.0107 (16)0.0044 (14)0.0015 (13)0.0030 (13)
C60.0185 (17)0.0126 (15)0.0114 (16)0.0046 (13)0.0061 (14)0.0027 (13)
C70.0180 (17)0.0180 (17)0.0099 (16)0.0072 (14)−0.0003 (13)0.0043 (13)
C80.0159 (17)0.0236 (18)0.0126 (17)0.0076 (14)0.0010 (14)0.0061 (14)
C90.0120 (16)0.0209 (17)0.0161 (18)0.0077 (14)0.0045 (14)0.0045 (14)
C100.0124 (15)0.0120 (15)0.0089 (15)0.0056 (12)0.0025 (12)0.0011 (12)
C110.0145 (16)0.0158 (16)0.0118 (16)0.0062 (13)0.0025 (13)0.0034 (13)
C120.0108 (16)0.0208 (17)0.0123 (17)0.0054 (13)0.0003 (13)0.0038 (13)
C130.0146 (17)0.0199 (17)0.0152 (18)0.0041 (14)0.0063 (14)0.0062 (14)
C140.0206 (18)0.0153 (16)0.0152 (18)0.0056 (14)0.0069 (14)0.0066 (14)
C150.0151 (16)0.0123 (15)0.0082 (16)0.0029 (13)0.0004 (13)−0.0002 (12)
C160.0197 (18)0.0145 (16)0.0127 (17)0.0105 (14)0.0021 (14)0.0048 (13)
C170.0143 (17)0.0208 (17)0.0127 (17)0.0093 (14)0.0009 (13)0.0043 (14)
C180.0121 (16)0.0171 (16)0.0143 (17)0.0081 (13)0.0049 (13)0.0045 (13)
C190.0193 (19)0.027 (2)0.029 (2)0.0051 (16)0.0007 (17)−0.0014 (17)

Geometric parameters (Å, °)

Zn1—O22.030 (2)C7—C81.372 (5)
Zn1—N22.040 (3)C7—H70.9500
Zn1—N12.050 (3)C8—C91.411 (5)
Zn1—O12.340 (2)C8—H80.9500
Zn1—Br12.3911 (5)C9—H90.9500
O1—C21.362 (4)C10—C151.409 (5)
O2—C111.328 (4)C10—C111.445 (5)
O2—H20.8400C11—C121.383 (5)
O3—C191.430 (5)C12—C131.404 (5)
O3—H30.8400C12—H120.9500
N1—C91.319 (4)C13—C141.378 (5)
N1—C11.372 (4)C13—H130.9500
N2—C181.322 (4)C14—C151.410 (5)
N2—C101.361 (4)C14—H140.9500
C1—C21.414 (5)C15—C161.417 (5)
C1—C61.418 (5)C16—C171.364 (5)
C2—C31.368 (5)C16—H160.9500
C3—C41.422 (5)C17—C181.406 (5)
C3—H3A0.9500C17—H170.9500
C4—C51.376 (5)C18—H180.9500
C4—H40.9500C19—H19A0.9800
C5—C61.416 (5)C19—H19B0.9800
C5—H50.9500C19—H19C0.9800
C6—C71.412 (5)
O2—Zn1—N282.51 (11)C6—C7—H7120.1
O2—Zn1—N195.88 (11)C7—C8—C9118.8 (3)
N2—Zn1—N1143.75 (11)C7—C8—H8120.6
O2—Zn1—O1150.98 (10)C9—C8—H8120.6
N2—Zn1—O190.06 (10)N1—C9—C8123.4 (3)
N1—Zn1—O173.91 (10)N1—C9—H9118.3
O2—Zn1—Br1112.41 (7)C8—C9—H9118.3
N2—Zn1—Br1109.66 (8)N2—C10—C15122.9 (3)
N1—Zn1—Br1104.40 (8)N2—C10—C11116.5 (3)
O1—Zn1—Br196.52 (6)C15—C10—C11120.7 (3)
C2—O1—Zn1108.4 (2)O2—C11—C12124.4 (3)
C11—O2—Zn1111.3 (2)O2—C11—C10118.4 (3)
C11—O2—H2124.4C12—C11—C10117.2 (3)
Zn1—O2—H2124.4C11—C12—C13121.4 (3)
C19—O3—H3109.5C11—C12—H12119.3
C9—N1—C1118.4 (3)C13—C12—H12119.3
C9—N1—Zn1122.8 (2)C14—C13—C12121.9 (3)
C1—N1—Zn1117.2 (2)C14—C13—H13119.0
C18—N2—C10119.0 (3)C12—C13—H13119.0
C18—N2—Zn1129.8 (2)C13—C14—C15118.6 (3)
C10—N2—Zn1110.8 (2)C13—C14—H14120.7
N1—C1—C2117.6 (3)C15—C14—H14120.7
N1—C1—C6122.0 (3)C10—C15—C14120.1 (3)
C2—C1—C6120.3 (3)C10—C15—C16116.4 (3)
O1—C2—C3124.0 (3)C14—C15—C16123.5 (3)
O1—C2—C1116.0 (3)C17—C16—C15120.2 (3)
C3—C2—C1119.9 (3)C17—C16—H16119.9
C2—C3—C4119.9 (3)C15—C16—H16119.9
C2—C3—H3A120.0C16—C17—C18119.3 (3)
C4—C3—H3A120.0C16—C17—H17120.4
C5—C4—C3121.2 (3)C18—C17—H17120.4
C5—C4—H4119.4N2—C18—C17122.2 (3)
C3—C4—H4119.4N2—C18—H18118.9
C4—C5—C6119.7 (3)C17—C18—H18118.9
C4—C5—H5120.2O3—C19—H19A109.5
C6—C5—H5120.2O3—C19—H19B109.5
C7—C6—C5123.5 (3)H19A—C19—H19B109.5
C7—C6—C1117.5 (3)O3—C19—H19C109.5
C5—C6—C1118.9 (3)H19A—C19—H19C109.5
C8—C7—C6119.8 (3)H19B—C19—H19C109.5
C8—C7—H7120.1
O2—Zn1—O1—C294.6 (3)C4—C5—C6—C7−177.0 (3)
N2—Zn1—O1—C2169.1 (2)C4—C5—C6—C10.9 (5)
N1—Zn1—O1—C222.0 (2)N1—C1—C6—C7−4.1 (5)
Br1—Zn1—O1—C2−81.1 (2)C2—C1—C6—C7176.7 (3)
N2—Zn1—O2—C116.3 (2)N1—C1—C6—C5177.9 (3)
N1—Zn1—O2—C11149.9 (2)C2—C1—C6—C5−1.3 (5)
O1—Zn1—O2—C1182.7 (3)C5—C6—C7—C8178.5 (3)
Br1—Zn1—O2—C11−101.9 (2)C1—C6—C7—C80.6 (5)
O2—Zn1—N1—C921.6 (3)C6—C7—C8—C92.0 (5)
N2—Zn1—N1—C9106.9 (3)C1—N1—C9—C8−1.9 (5)
O1—Zn1—N1—C9173.8 (3)Zn1—N1—C9—C8162.7 (3)
Br1—Zn1—N1—C9−93.4 (3)C7—C8—C9—N1−1.4 (6)
O2—Zn1—N1—C1−173.6 (2)C18—N2—C10—C15−1.2 (5)
N2—Zn1—N1—C1−88.3 (3)Zn1—N2—C10—C15−174.5 (3)
O1—Zn1—N1—C1−21.3 (2)C18—N2—C10—C11178.6 (3)
Br1—Zn1—N1—C171.4 (2)Zn1—N2—C10—C115.2 (4)
O2—Zn1—N2—C18−178.6 (3)Zn1—O2—C11—C12175.2 (3)
N1—Zn1—N2—C1891.6 (3)Zn1—O2—C11—C10−5.4 (4)
O1—Zn1—N2—C1829.5 (3)N2—C10—C11—O20.1 (5)
Br1—Zn1—N2—C18−67.5 (3)C15—C10—C11—O2179.8 (3)
O2—Zn1—N2—C10−6.2 (2)N2—C10—C11—C12179.6 (3)
N1—Zn1—N2—C10−96.0 (3)C15—C10—C11—C12−0.7 (5)
O1—Zn1—N2—C10−158.1 (2)O2—C11—C12—C13−179.9 (3)
Br1—Zn1—N2—C10104.9 (2)C10—C11—C12—C130.7 (5)
C9—N1—C1—C2−176.1 (3)C11—C12—C13—C14−0.2 (6)
Zn1—N1—C1—C218.4 (4)C12—C13—C14—C15−0.3 (5)
C9—N1—C1—C64.7 (5)N2—C10—C15—C14179.9 (3)
Zn1—N1—C1—C6−160.8 (3)C11—C10—C15—C140.2 (5)
Zn1—O1—C2—C3161.4 (3)N2—C10—C15—C160.5 (5)
Zn1—O1—C2—C1−20.0 (3)C11—C10—C15—C16−179.2 (3)
N1—C1—C2—O13.7 (4)C13—C14—C15—C100.3 (5)
C6—C1—C2—O1−177.1 (3)C13—C14—C15—C16179.7 (3)
N1—C1—C2—C3−177.7 (3)C10—C15—C16—C171.0 (5)
C6—C1—C2—C31.6 (5)C14—C15—C16—C17−178.5 (3)
O1—C2—C3—C4177.1 (3)C15—C16—C17—C18−1.7 (5)
C1—C2—C3—C4−1.4 (5)C10—N2—C18—C170.4 (5)
C2—C3—C4—C51.0 (6)Zn1—N2—C18—C17172.3 (3)
C3—C4—C5—C6−0.8 (5)C16—C17—C18—N21.0 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.841.902.585 (4)137
O3—H3···O10.841.712.551 (4)178

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5356).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Najafi, E., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m1276. [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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