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In the title compound, [Zn(C10H7NO3)2(H2O)], the Zn atom is pentacoordinated and has a square pyramidal geometry. The Zn atom is coordinated by two N and two O atoms of the two organic ligands, forming the square plane. One aqua O atom occupies the vertex of the square pyramid. The N and O atoms of the ligands lie in trans positions with respect to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007840/cv6181sup1.cif
Contains datablocks globall, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007840/cv6181Isup2.hkl
Contains datablock I

CCDC reference: 214563

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.049
  • wR factor = 0.170
  • Data-to-parameter ratio = 15.8

checkCIF results

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ADDSYM reports no extra symmetry








Comment top

Quinoline-2-carboxylic acid is a tryptophan metabolite (Martell & Smith, 1974). Crystal strutures of its metal complexes have been determined as copper(II) (Haendler, 1986), manganese(II) (Haendler, 1996; Okabe & Koizumi, 1997), iron(II), cobalt(II) (Okabe & Makino, 1998, 1999), zinc(II) (Zevaco et al., 1998), nickel(II) (Odoko et al., 2001) and vanadium(IV) (Okabe & Muranishi, 2002) complexes. In these complexes, the Zn complex is considered as the efficient catalyst for potential carbon dioxide activator (Zevaco et al., 1998). Although the Zn complex was already determined as the anhydrous complex (Zevaco et al., 1998), [Zn(2-quinolinecarboxylato)2(1-methylimidazole)2], in which the Zn atom is hexacoordinated, and exhibits a slightly distorted octahedral geometry. The structure of the title Zn complex, (I), with a square-pyramidal geometry is shown in Fig. 1, and selected geometric parameters are listed in Table 1.

The Zn atom is pentacoordinated. The structure of (I) resembles the Cu complex (Haendler, 1986). The Zn atom is coordinated by two N and two O atoms of the two quinaldinate ligands which form the square plane and one aqua O atom occupies the vertex of the square pyramid. The N and O atoms of the ligands lie in trans positions with respect to each other. The organic ligands and the central Zn atom form five-membered rings which are usually observed in the metal compounds of quinoline-2-carboxylic acid Okabe & Makino, 1999). The Zn—O(carboxylate) and Zn—N distances in (I) (Table 1) are shorter than those in hexacoordinated Zn complex with octahedral geometry (Zevaco et al., 1998), that may indicate on preferred stability of Zn complex in a square pyramidal coordination in comparison with a distorted octahedral geometry. In the crystal packing shown in Fig. 2, quinoline rings of the complex form stacks along the b axis. The water molecules form a hydrogen-bonding network (Table 2).

Experimental top

The purple plate crystal was obtained by slow evapolation from the mixture of quinoline-2-carboxylic acid and Fe(NH4)2(SO4)2·6H2O (4:1) dissolved in water.

Refinement top

All H atoms were located from the difference Fourier maps, and the H atoms of the quinoline rings were regenerated at the ideal positions by riding models using SHELXL HFIX instructions. The H atoms of the water molecules were left at the positions located in the Fourier maps, since they were not idealized with the SHELXL SADI restriction.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Scheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme and 50% probability ellipsoids.
[Figure 2] Fig. 2. Molecular packing of (I).
(I) top
Crystal data top
[Zn(C10H7NO3)2(H2O)]F(000) = 872.0
Mr = 427.72Dx = 1.629 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 22 reflections
a = 7.716 (4) Åθ = 12.2–14.4°
b = 7.564 (6) ŵ = 1.45 mm1
c = 30.037 (3) ÅT = 296 K
β = 95.97 (2)°Plate, purple
V = 1743.6 (17) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.048
ω scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 010
Tmin = 0.771, Tmax = 0.865k = 09
4602 measured reflectionsl = 3938
3985 independent reflections3 standard reflections every 150 reflections
2001 reflections with I > 2σ(I) intensity decay: 0.04%
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.170(Δ/σ)max = 0.001
S = 0.89Δρmax = 0.72 e Å3
3985 reflectionsΔρmin = 0.45 e Å3
253 parameters
Crystal data top
[Zn(C10H7NO3)2(H2O)]V = 1743.6 (17) Å3
Mr = 427.72Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.716 (4) ŵ = 1.45 mm1
b = 7.564 (6) ÅT = 296 K
c = 30.037 (3) Å0.20 × 0.15 × 0.10 mm
β = 95.97 (2)°
Data collection top
Rigaku AFC-5R
diffractometer
2001 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.048
Tmin = 0.771, Tmax = 0.8653 standard reflections every 150 reflections
4602 measured reflections intensity decay: 0.04%
3985 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049253 parameters
wR(F2) = 0.170H-atom parameters not refined
S = 0.89Δρmax = 0.72 e Å3
3985 reflectionsΔρmin = 0.45 e Å3
Special details top

Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.18189 (6)0.24548 (8)0.38134 (2)0.0346 (2)
O10.2641 (5)0.0026 (5)0.3964 (1)0.0445 (9)
O1W0.3659 (4)0.4241 (5)0.3979 (1)0.0393 (8)
O20.3310 (6)0.2557 (5)0.3653 (1)0.066 (1)
O30.0562 (4)0.3209 (5)0.3564 (1)0.0450 (9)
O40.3283 (5)0.3556 (7)0.3714 (1)0.059 (1)
N10.2482 (5)0.1610 (6)0.3171 (1)0.0335 (9)
N20.0544 (5)0.2645 (5)0.4414 (1)0.0329 (8)
C10.2946 (6)0.0059 (7)0.3186 (2)0.035 (1)
C20.3350 (7)0.1025 (7)0.2810 (2)0.042 (1)
C30.3189 (7)0.0210 (8)0.2405 (2)0.048 (1)
C40.2644 (7)0.1550 (7)0.2370 (2)0.040 (1)
C50.2405 (8)0.2459 (9)0.1955 (2)0.051 (1)
C60.1865 (8)0.4182 (8)0.1940 (2)0.053 (1)
C70.1575 (7)0.5061 (7)0.2329 (2)0.046 (1)
C80.1805 (7)0.4237 (7)0.2735 (2)0.040 (1)
C90.2328 (5)0.2454 (7)0.2763 (1)0.0336 (9)
C100.2990 (7)0.0981 (8)0.3636 (2)0.042 (1)
C110.1113 (6)0.3040 (6)0.4325 (2)0.035 (1)
C120.2256 (7)0.3220 (8)0.4657 (2)0.046 (1)
C130.1615 (7)0.2944 (8)0.5092 (2)0.051 (2)
C140.0142 (7)0.2484 (8)0.5199 (2)0.042 (1)
C150.0920 (8)0.2178 (8)0.5644 (2)0.053 (2)
C160.2622 (9)0.1780 (9)0.5720 (2)0.061 (2)
C170.3686 (8)0.1666 (9)0.5371 (2)0.052 (1)
C180.2997 (7)0.1951 (8)0.4943 (2)0.044 (1)
C190.1228 (6)0.2370 (7)0.4848 (2)0.036 (1)
C200.1724 (6)0.3295 (8)0.3832 (2)0.040 (1)
H1A0.46860.40990.39410.0471*
H1B0.33930.52240.38770.0471*
H20.37190.21940.28380.0502*
H30.34400.08230.21520.0576*
H50.26160.18820.16930.0618*
H60.16910.47660.16660.0631*
H70.12160.62350.23140.0549*
H80.16170.48530.29930.0475*
H120.34190.35210.45830.0551*
H130.23430.30600.53190.0609*
H150.02460.22550.58830.0630*
H160.31060.15760.60120.0736*
H170.48620.13960.54320.0625*
H180.37030.18680.47120.0525*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0352 (3)0.0412 (3)0.0287 (3)0.0048 (3)0.0089 (2)0.0024 (3)
O10.063 (2)0.040 (2)0.032 (2)0.011 (2)0.011 (2)0.010 (2)
O1W0.036 (2)0.040 (2)0.044 (2)0.003 (2)0.012 (1)0.008 (2)
O20.105 (4)0.035 (2)0.058 (3)0.013 (3)0.007 (2)0.009 (2)
O30.035 (2)0.069 (2)0.032 (2)0.010 (2)0.010 (1)0.002 (2)
O40.038 (2)0.092 (3)0.048 (2)0.011 (2)0.010 (2)0.006 (2)
N10.037 (2)0.034 (2)0.030 (2)0.005 (2)0.007 (2)0.001 (2)
N20.037 (2)0.034 (2)0.029 (2)0.000 (2)0.010 (1)0.002 (2)
C10.040 (3)0.037 (3)0.029 (2)0.001 (2)0.004 (2)0.001 (2)
C20.049 (3)0.033 (3)0.044 (3)0.009 (2)0.006 (2)0.009 (2)
C30.054 (3)0.054 (4)0.037 (3)0.001 (3)0.010 (2)0.012 (3)
C40.043 (3)0.042 (3)0.037 (3)0.003 (3)0.009 (2)0.007 (2)
C50.067 (3)0.058 (3)0.031 (2)0.001 (4)0.012 (2)0.004 (3)
C60.065 (4)0.057 (4)0.037 (3)0.000 (3)0.012 (3)0.010 (3)
C70.056 (3)0.037 (3)0.044 (3)0.002 (3)0.006 (2)0.007 (2)
C80.047 (3)0.041 (3)0.031 (2)0.001 (3)0.007 (2)0.003 (2)
C90.031 (2)0.041 (3)0.030 (2)0.002 (3)0.007 (2)0.002 (3)
C100.048 (3)0.039 (3)0.039 (3)0.002 (3)0.002 (2)0.002 (2)
C110.038 (3)0.033 (3)0.036 (3)0.003 (2)0.013 (2)0.007 (2)
C120.036 (3)0.062 (3)0.042 (3)0.000 (3)0.016 (2)0.002 (3)
C130.049 (3)0.070 (4)0.038 (3)0.009 (3)0.023 (2)0.004 (3)
C140.049 (3)0.048 (3)0.031 (2)0.009 (3)0.013 (2)0.004 (3)
C150.064 (4)0.067 (5)0.029 (2)0.009 (3)0.015 (2)0.001 (3)
C160.076 (4)0.080 (4)0.027 (3)0.004 (4)0.006 (3)0.008 (3)
C170.054 (3)0.064 (4)0.039 (3)0.000 (3)0.004 (2)0.003 (3)
C180.045 (3)0.053 (3)0.034 (3)0.005 (2)0.007 (2)0.006 (2)
C190.040 (2)0.039 (3)0.031 (2)0.003 (3)0.010 (2)0.000 (2)
C200.037 (3)0.047 (3)0.037 (3)0.003 (2)0.010 (2)0.001 (2)
Geometric parameters (Å, º) top
Zn1—O12.017 (4)C5—H50.930
Zn1—O1W1.986 (3)C6—C71.383 (8)
Zn1—O31.994 (4)C6—H60.930
Zn1—N12.144 (4)C7—C81.364 (7)
Zn1—N22.147 (4)C7—H70.930
O1—C101.272 (7)C8—C91.407 (8)
O1W—H1A0.820C8—H80.930
O1W—H1B0.822C11—C121.406 (8)
O2—C101.217 (7)C11—C201.520 (7)
O3—C201.268 (6)C12—C131.365 (7)
O4—C201.234 (6)C12—H120.930
N1—C11.312 (7)C13—C141.404 (8)
N1—C91.378 (6)C13—H130.930
N2—C111.314 (6)C14—C151.426 (7)
N2—C191.372 (6)C14—C191.416 (7)
C1—C21.407 (7)C15—C161.344 (9)
C1—C101.519 (7)C15—H150.930
C2—C31.357 (7)C16—C171.401 (9)
C2—H20.930C16—H160.930
C3—C41.397 (8)C17—C181.354 (7)
C3—H30.930C17—H170.930
C4—C51.418 (8)C18—C191.401 (7)
C4—C91.405 (7)C18—H180.930
C5—C61.368 (9)
O1···C15i3.501 (7)O4···C3vi3.498 (7)
O1···C17ii3.520 (7)N1···C7v3.529 (7)
O1W···O2iii2.616 (5)C2···C5vii3.473 (8)
O1W···O4iv2.620 (5)C2···C7viii3.510 (8)
O2···C16ii3.539 (8)C7···C9vi3.500 (7)
O3···C6v3.501 (7)C13···C19ix3.561 (8)
O3···C3vi3.575 (6)
O1—Zn1—O1W112.2 (1)C8—C7—H7119.4
O1—Zn1—O3127.3 (2)C7—C8—C9120.0 (5)
O1—Zn1—N179.9 (1)C7—C8—H8120.0
O1—Zn1—N292.0 (1)C9—C8—H8120.0
O1W—Zn1—O3120.4 (2)N1—C9—C4121.0 (5)
O1W—Zn1—N1101.4 (1)N1—C9—C8119.6 (4)
O1W—Zn1—N297.0 (1)C4—C9—C8119.4 (4)
O3—Zn1—N192.5 (1)O1—C10—O2125.7 (5)
O3—Zn1—N279.2 (1)O1—C10—C1116.1 (5)
N1—Zn1—N2161.6 (1)O2—C10—C1118.1 (5)
Zn1—O1—C10116.3 (3)N2—C11—C12123.2 (4)
Zn1—O1W—H1A123.5N2—C11—C20115.1 (4)
Zn1—O1W—H1B112.1C12—C11—C20121.8 (4)
H1A—O1W—H1B105.9C11—C12—C13118.3 (5)
Zn1—O3—C20117.4 (3)C11—C12—H12120.8
Zn1—N1—C1110.2 (3)C13—C12—H12120.9
Zn1—N1—C9131.1 (3)C12—C13—C14120.1 (5)
C1—N1—C9118.3 (4)C12—C13—H13119.9
Zn1—N2—C11111.5 (3)C14—C13—H13119.9
Zn1—N2—C19128.6 (3)C13—C14—C15123.8 (5)
C11—N2—C19119.9 (4)C13—C14—C19118.5 (4)
N1—C1—C2123.7 (4)C15—C14—C19117.7 (5)
N1—C1—C10117.0 (4)C14—C15—C16120.2 (5)
C2—C1—C10119.3 (4)C14—C15—H15119.9
C1—C2—C3118.4 (5)C16—C15—H15119.9
C1—C2—H2120.8C15—C16—C17121.7 (5)
C3—C2—H2120.8C15—C16—H16119.1
C2—C3—C4120.0 (5)C17—C16—H16119.1
C2—C3—H3120.0C16—C17—C18119.8 (5)
C4—C3—H3120.0C16—C17—H17120.1
C3—C4—C5122.6 (5)C18—C17—H17120.1
C3—C4—C9118.5 (5)C17—C18—C19120.5 (5)
C5—C4—C9118.9 (5)C17—C18—H18119.7
C4—C5—C6120.2 (5)C19—C18—H18119.7
C4—C5—H5119.9N2—C19—C14120.0 (4)
C6—C5—H5119.9N2—C19—C18119.9 (4)
C5—C6—C7120.3 (5)C14—C19—C18120.0 (4)
C5—C6—H6119.8O3—C20—O4124.0 (5)
C7—C6—H6119.9O3—C20—C11116.4 (4)
C6—C7—C8121.2 (5)O4—C20—C11119.6 (5)
C6—C7—H7119.4
Zn1—O1—C10—O2171.2 (4)N1—C9—C8—C7177.1 (5)
Zn1—O1—C10—C17.0 (6)N2—Zn1—O1—C10156.9 (4)
Zn1—O3—C20—O4171.9 (5)N2—Zn1—O3—C206.2 (4)
Zn1—O3—C20—C117.6 (6)N2—Zn1—N1—C160.7 (6)
Zn1—N1—C1—C2175.9 (4)N2—Zn1—N1—C9112.0 (5)
Zn1—N1—C1—C102.4 (5)N2—C11—C12—C131.1 (8)
Zn1—N1—C9—C4171.7 (3)N2—C19—C14—C132.3 (8)
Zn1—N1—C9—C86.8 (6)N2—C19—C14—C15179.7 (5)
Zn1—N2—C11—C12179.1 (4)N2—C19—C18—C17179.6 (5)
Zn1—N2—C11—C201.0 (5)C1—N1—C9—C40.6 (6)
Zn1—N2—C19—C14177.1 (4)C1—N1—C9—C8179.0 (4)
Zn1—N2—C19—C182.0 (7)C1—C2—C3—C40.4 (8)
O1—Zn1—O3—C2078.0 (4)C2—C1—N1—C92.1 (7)
O1—Zn1—N1—C14.5 (3)C2—C3—C4—C5178.2 (5)
O1—Zn1—N1—C9177.2 (4)C2—C3—C4—C92.0 (8)
O1—Zn1—N2—C11124.1 (3)C3—C2—C1—C10175.6 (5)
O1—Zn1—N2—C1954.2 (4)C3—C4—C5—C6179.8 (5)
O1—C10—C1—N12.8 (7)C3—C4—C9—C8179.0 (5)
O1—C10—C1—C2178.9 (5)C4—C5—C6—C71.1 (9)
O1W—Zn1—O1—C10104.7 (4)C4—C9—C8—C71.4 (7)
O1W—Zn1—O3—C2098.0 (4)C5—C4—C9—C80.8 (7)
O1W—Zn1—N1—C1115.3 (3)C5—C6—C7—C80.5 (9)
O1W—Zn1—N1—C972.0 (4)C6—C5—C4—C90.4 (8)
O1W—Zn1—N2—C11123.3 (3)C6—C7—C8—C90.8 (8)
O1W—Zn1—N2—C1958.4 (4)C9—N1—C1—C10176.2 (4)
O2—C10—C1—N1175.4 (5)C11—N2—C19—C141.0 (7)
O2—C10—C1—C22.9 (7)C11—N2—C19—C18179.9 (5)
O3—Zn1—O1—C1079.0 (4)C11—C12—C13—C140.3 (9)
O3—Zn1—N1—C1123.0 (3)C12—C11—N2—C190.7 (7)
O3—Zn1—N1—C949.7 (4)C12—C13—C14—C15179.7 (6)
O3—Zn1—N2—C113.6 (3)C12—C13—C14—C191.9 (8)
O3—Zn1—N2—C19178.2 (4)C13—C12—C11—C20179.0 (5)
O3—C20—C11—N24.2 (7)C13—C14—C15—C16178.5 (6)
O3—C20—C11—C12175.8 (5)C13—C14—C19—C18178.7 (5)
O4—C20—C11—N2175.4 (5)C14—C15—C16—C170.5 (10)
O4—C20—C11—C124.7 (8)C14—C19—C18—C170.5 (8)
N1—Zn1—O1—C106.4 (4)C15—C14—C19—C180.6 (8)
N1—Zn1—O3—C20157.2 (4)C15—C16—C17—C180 (1)
N1—Zn1—N2—C1160.7 (6)C16—C15—C14—C190.6 (9)
N1—Zn1—N2—C19117.6 (5)C16—C17—C18—C190.4 (9)
N1—C1—C2—C32.6 (8)C19—N2—C11—C20179.4 (4)
N1—C9—C4—C32.5 (7)C19—N2—C11—C20179.4 (4)
N1—C9—C4—C5177.7 (4)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) x, y1/2, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y1/2, z+1/2; (viii) x, y1, z; (ix) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O2iii0.821.812.616 (5)168
O1W—H1A···O4iv0.821.822.620 (5)165
Symmetry codes: (iii) x, y+1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Zn(C10H7NO3)2(H2O)]
Mr427.72
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.716 (4), 7.564 (6), 30.037 (3)
β (°) 95.97 (2)
V3)1743.6 (17)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.771, 0.865
No. of measured, independent and
observed [I > 2σ(I)] reflections
4602, 3985, 2001
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.170, 0.89
No. of reflections3985
No. of parameters253
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.72, 0.45

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation and Rigaku, 1999), SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Scheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
Zn1—O12.017 (4)Zn1—N12.144 (4)
Zn1—O1W1.986 (3)Zn1—N22.147 (4)
Zn1—O31.994 (4)
O1—Zn1—O1W112.2 (1)O1W—Zn1—N1101.4 (1)
O1—Zn1—O3127.3 (2)O1W—Zn1—N297.0 (1)
O1—Zn1—N179.9 (1)O3—Zn1—N192.5 (1)
O1—Zn1—N292.0 (1)O3—Zn1—N279.2 (1)
O1W—Zn1—O3120.4 (2)N1—Zn1—N2161.6 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O2i0.821.812.616 (5)168
O1W—H1A···O4ii0.821.822.620 (5)165
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
 

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