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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m288.
Published online 2010 February 13. doi:  10.1107/S160053681000471X
PMCID: PMC2983540

Aqua­[N-phenyl-2-(quinolin-8-yl­oxy)acetamide]dinitratozinc(II)

Abstract

In the title complex, [Zn(NO3)2(C17H14N2O2)(H2O)], the six-coordinated Zn atom is in a distorted octa­hedral geometry, the donor centers being two O atoms and one N atom from the tridentate organic ligand, a water O atom and two O atoms from two monodentate nitrate ions. In the crystal, O—H(...)O hydrogen bonds between the coordinated water mol­ecules and nitrate O atoms and N—H(...)O hydrogen bonds between the main ligand and nitrate O atoms consolidate the three-dimensional network.

Related literature

For the synthesis of N-phenyl-2-(quinolin-8-yl­oxy)acetamide, see: Li et al. (2005 [triangle]); Wu et al. (2006 [triangle]). For the crystal structure of the hydrate of this mol­ecule, see: Li et al. (2005 [triangle]). For the coordination ability of related amides to lanthanides, see: Cai & Tan (2002 [triangle]); Wu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m288-scheme1.jpg

Experimental

Crystal data

  • [Zn(NO3)2(C17H14N2O2)(H2O)]
  • M r = 485.71
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m288-efi1.jpg
  • a = 7.9980 (14) Å
  • b = 9.5109 (16) Å
  • c = 13.359 (2) Å
  • α = 94.876 (2)°
  • β = 96.496 (2)°
  • γ = 106.031 (2)°
  • V = 963.2 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.34 mm−1
  • T = 296 K
  • 0.30 × 0.19 × 0.11 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.745, T max = 0.863
  • 10541 measured reflections
  • 4030 independent reflections
  • 3454 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.093
  • S = 1.05
  • 4030 reflections
  • 281 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681000471X/bh2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000471X/bh2270Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Henan Administration of Science and Technology (grant No. 092102210363), the Main Teacher Project of Henan Province (grant No. 649082) and the Doctoral Foundation of Henan Polytechnic University (B2009–65 648359 and B2009–70 648364).

supplementary crystallographic information

Comment

Including our previous work (Wu et al., 2006), the amide type ligands have been widely used to enhance the luminescent emissions of the lanthanide ions because of their excellent coordination ability (Cai & Tan, 2002). However, little work has been done on their transition metal complexes. Therefore, as part of our ongoing studies of the amide type ligands, the title complex was synthesized and characterized by X-ray diffraction.

As shown in Fig. 1, in the title complex, the six-coordinated Zn atom is in a distorted octahedral geometry with the donor centers of two O atoms and one N atom from the ligand, one O atom from one water molecule and two O atoms from two nitrate ions. The dihedral angle between phenyl ring and naphthyl ring is 22.5 (1)°.

In the crystal, O—H···O hydrogen bonds between the coordinated water molecules and nitrate O atoms, and N—H···O hydrogen bonds between the ligands and nitrate O atoms are helpful to consolidate the three-dimensional network (Fig. 2).

Experimental

N-phenyl-2-(quinolin-8-yloxy)acetamide (Wu et al., 2006; Li et al., 2005) (0.278 g, 1 mmol) was dissolved in acetonitrile (10 ml), then an acetonitrile solution (10 ml) containing zinc nitrate hexahydrate (0.295 g, 1 mmol) was added dropwise at room temperature. After stirring for 2 h, the mixture was filtered and set aside to crystallize at room temperature for 8 d, giving colorless prismatic crystals.

Refinement

Atoms H9A and H9B (water molecule O9) were located in a difference map and their positions fixed, with Uiso(H) = 1.5Ueq(O9). Other H atoms bonded to C and N atoms were placed in calculated positions and treated using a riding-model approximation [aromatic groups: C—H = 0.93 Å and Uiso(H) = 1.2Ueq(carrier C); methylene group: C—H = 0.97 Å and Uiso(H) = 1.2Ueq(carrier C); amine group: N—H = 0.86 Å and Uiso(H2) = 1.2Ueq(N2)].

Figures

Fig. 1.
The molecular structure shown with 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing for the title complex via hydrogen bonds (dashed lines).

Crystal data

[Zn(NO3)2(C17H14N2O2)(H2O)]Z = 2
Mr = 485.71F(000) = 496
Triclinic, P1Dx = 1.675 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9980 (14) ÅCell parameters from 4639 reflections
b = 9.5109 (16) Åθ = 2.6–26.4°
c = 13.359 (2) ŵ = 1.34 mm1
α = 94.876 (2)°T = 296 K
β = 96.496 (2)°Prism, colorless
γ = 106.031 (2)°0.30 × 0.19 × 0.11 mm
V = 963.2 (3) Å3

Data collection

Bruker SMART CCD diffractometer4030 independent reflections
Radiation source: fine-focus sealed tube3454 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 26.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −10→10
Tmin = 0.745, Tmax = 0.863k = −11→11
10541 measured reflectionsl = −16→16

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1851P] where P = (Fo2 + 2Fc2)/3
4030 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.39 e Å3

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

xyzUiso*/Ueq
Zn10.40610 (3)0.96202 (3)0.180722 (18)0.03178 (10)
O10.3965 (2)0.74601 (17)0.24213 (12)0.0397 (4)
O20.2694 (2)0.78947 (17)0.06551 (12)0.0379 (4)
O30.1934 (2)0.9611 (2)0.25329 (13)0.0468 (4)
O4−0.0719 (3)0.9596 (3)0.26368 (17)0.0721 (6)
O50.0289 (3)0.9897 (3)0.12235 (16)0.0820 (8)
O60.4097 (3)1.1192 (2)0.08737 (14)0.0524 (5)
O70.3915 (4)1.2818 (2)0.20478 (17)0.0757 (7)
O80.3628 (4)1.3175 (2)0.04674 (17)0.0769 (7)
O90.6309 (2)0.9394 (2)0.12457 (14)0.0566 (5)
H9A0.61020.92050.06260.085*
H9B0.73720.94030.15130.085*
N10.5583 (2)1.0166 (2)0.32636 (13)0.0337 (4)
N20.2226 (3)0.5535 (2)−0.00405 (15)0.0401 (5)
H20.23060.46950.01170.048*
N30.0477 (3)0.9699 (2)0.21100 (16)0.0447 (5)
N40.3863 (3)1.2425 (2)0.11447 (17)0.0480 (5)
C10.6333 (3)1.1531 (3)0.36958 (19)0.0450 (6)
H10.61031.23010.33750.054*
C20.7469 (4)1.1865 (3)0.4625 (2)0.0530 (7)
H2A0.79611.28400.49120.064*
C30.7839 (4)1.0767 (3)0.50957 (19)0.0528 (7)
H30.86051.09850.57030.063*
C40.7068 (3)0.9290 (3)0.46704 (17)0.0431 (6)
C50.7382 (4)0.8075 (4)0.5099 (2)0.0566 (7)
H50.81260.82230.57110.068*
C60.6612 (4)0.6687 (4)0.4632 (2)0.0608 (8)
H60.68420.58970.49270.073*
C70.5464 (4)0.6413 (3)0.37011 (19)0.0510 (7)
H70.49580.54560.33830.061*
C80.5119 (3)0.7573 (3)0.32834 (17)0.0370 (5)
C90.5925 (3)0.9046 (3)0.37403 (16)0.0343 (5)
C100.3655 (3)0.6234 (3)0.16737 (18)0.0411 (5)
H10A0.28770.53630.18800.049*
H10B0.47500.60330.15670.049*
C110.2808 (3)0.6650 (2)0.07116 (17)0.0339 (5)
C120.1501 (3)0.5535 (3)−0.10558 (18)0.0381 (5)
C130.1263 (4)0.4259 (3)−0.1706 (2)0.0494 (6)
H130.15770.3465−0.14650.059*
C140.0558 (4)0.4166 (3)−0.2714 (2)0.0610 (8)
H140.04080.3311−0.31500.073*
C150.0081 (4)0.5329 (3)−0.3068 (2)0.0629 (8)
H15−0.03940.5267−0.37440.076*
C160.0308 (4)0.6595 (3)−0.2417 (2)0.0604 (8)
H16−0.00180.7382−0.26610.072*
C170.1011 (4)0.6711 (3)−0.1408 (2)0.0493 (6)
H170.11540.7566−0.09740.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03517 (16)0.03244 (16)0.02720 (15)0.01224 (11)−0.00243 (10)0.00149 (10)
O10.0471 (9)0.0359 (9)0.0332 (8)0.0153 (7)−0.0107 (7)−0.0015 (7)
O20.0448 (9)0.0303 (8)0.0348 (8)0.0113 (7)−0.0075 (7)−0.0007 (6)
O30.0357 (9)0.0719 (12)0.0367 (9)0.0229 (8)0.0013 (7)0.0082 (8)
O40.0428 (11)0.1124 (19)0.0713 (15)0.0334 (12)0.0168 (10)0.0182 (13)
O50.0611 (14)0.148 (2)0.0473 (13)0.0476 (15)−0.0026 (10)0.0271 (14)
O60.0806 (13)0.0421 (10)0.0500 (11)0.0342 (10)0.0243 (10)0.0164 (8)
O70.115 (2)0.0597 (14)0.0523 (13)0.0335 (13)0.0008 (12)−0.0042 (11)
O80.126 (2)0.0575 (13)0.0664 (14)0.0540 (14)0.0119 (13)0.0232 (11)
O90.0378 (10)0.0931 (15)0.0413 (10)0.0280 (10)0.0000 (8)−0.0016 (10)
N10.0325 (10)0.0397 (11)0.0271 (9)0.0100 (8)−0.0001 (7)0.0016 (8)
N20.0509 (12)0.0290 (10)0.0365 (11)0.0114 (9)−0.0060 (9)−0.0010 (8)
N30.0375 (11)0.0521 (13)0.0450 (12)0.0175 (9)−0.0009 (9)0.0022 (10)
N40.0587 (14)0.0367 (11)0.0504 (13)0.0177 (10)0.0046 (11)0.0070 (10)
C10.0481 (14)0.0432 (14)0.0376 (13)0.0074 (11)0.0004 (11)−0.0016 (11)
C20.0539 (16)0.0532 (16)0.0370 (14)−0.0016 (13)−0.0032 (12)−0.0062 (12)
C30.0450 (15)0.0700 (19)0.0307 (13)0.0029 (13)−0.0070 (11)−0.0007 (12)
C40.0370 (13)0.0630 (16)0.0257 (11)0.0110 (11)−0.0010 (9)0.0032 (11)
C50.0592 (17)0.079 (2)0.0327 (13)0.0256 (15)−0.0087 (12)0.0133 (14)
C60.077 (2)0.068 (2)0.0456 (16)0.0351 (17)−0.0035 (14)0.0193 (14)
C70.0645 (17)0.0495 (15)0.0398 (14)0.0212 (13)−0.0035 (12)0.0092 (12)
C80.0382 (12)0.0444 (13)0.0282 (11)0.0142 (10)−0.0012 (9)0.0045 (9)
C90.0299 (11)0.0461 (13)0.0263 (11)0.0110 (9)0.0023 (8)0.0043 (9)
C100.0516 (14)0.0333 (12)0.0362 (12)0.0150 (10)−0.0056 (10)−0.0008 (10)
C110.0323 (11)0.0328 (12)0.0340 (12)0.0080 (9)−0.0006 (9)0.0021 (9)
C120.0377 (12)0.0352 (12)0.0351 (12)0.0043 (9)−0.0016 (9)−0.0008 (9)
C130.0568 (16)0.0402 (14)0.0447 (14)0.0107 (12)−0.0035 (12)−0.0051 (11)
C140.072 (2)0.0539 (17)0.0426 (15)0.0062 (14)−0.0029 (14)−0.0165 (13)
C150.075 (2)0.0621 (19)0.0345 (14)0.0007 (15)−0.0108 (13)−0.0008 (13)
C160.073 (2)0.0503 (17)0.0489 (16)0.0117 (14)−0.0149 (14)0.0106 (13)
C170.0614 (17)0.0370 (13)0.0413 (14)0.0084 (12)−0.0077 (12)−0.0008 (11)

Geometric parameters (Å, °)

Zn1—O62.0231 (17)C3—C41.408 (4)
Zn1—O32.0494 (17)C3—H30.9300
Zn1—O92.0818 (17)C4—C51.403 (4)
Zn1—O22.1110 (15)C4—C91.418 (3)
Zn1—N12.1166 (17)C5—C61.354 (4)
Zn1—O12.2612 (16)C5—H50.9300
O1—C81.369 (3)C6—C71.418 (4)
O1—C101.416 (3)C6—H60.9300
O2—C111.220 (3)C7—C81.358 (3)
O3—N31.264 (3)C7—H70.9300
O4—N31.238 (3)C8—C91.421 (3)
O5—N31.214 (3)C10—C111.518 (3)
O6—N41.266 (3)C10—H10A0.9700
O7—N41.225 (3)C10—H10B0.9700
O8—N41.228 (3)C12—C171.384 (4)
O9—H9A0.8200C12—C131.385 (3)
O9—H9B0.8812C13—C141.385 (4)
N1—C11.320 (3)C13—H130.9300
N1—C91.360 (3)C14—C151.370 (4)
N2—C111.339 (3)C14—H140.9300
N2—C121.414 (3)C15—C161.379 (4)
N2—H20.8600C15—H150.9300
C1—C21.409 (4)C16—C171.384 (4)
C1—H10.9300C16—H160.9300
C2—C31.347 (4)C17—H170.9300
C2—H2A0.9300
O6—Zn1—O3103.05 (7)C5—C4—C3124.3 (2)
O6—Zn1—O986.57 (8)C5—C4—C9119.0 (2)
O3—Zn1—O9170.28 (7)C3—C4—C9116.6 (2)
O6—Zn1—O293.07 (7)C6—C5—C4120.6 (2)
O3—Zn1—O295.75 (7)C6—C5—H5119.7
O9—Zn1—O285.04 (7)C4—C5—H5119.7
O6—Zn1—N1120.13 (8)C5—C6—C7121.5 (3)
O3—Zn1—N186.60 (7)C5—C6—H6119.3
O9—Zn1—N187.29 (7)C7—C6—H6119.3
O2—Zn1—N1145.38 (7)C8—C7—C6118.8 (3)
O6—Zn1—O1163.42 (7)C8—C7—H7120.6
O3—Zn1—O186.10 (7)C6—C7—H7120.6
O9—Zn1—O184.93 (7)C7—C8—O1124.8 (2)
O2—Zn1—O172.04 (6)C7—C8—C9121.5 (2)
N1—Zn1—O173.67 (6)O1—C8—C9113.7 (2)
C8—O1—C10119.01 (18)N1—C9—C4122.7 (2)
C8—O1—Zn1114.78 (14)N1—C9—C8118.74 (19)
C10—O1—Zn1114.98 (13)C4—C9—C8118.6 (2)
C11—O2—Zn1120.10 (14)O1—C10—C11105.98 (18)
N3—O3—Zn1124.92 (15)O1—C10—H10A110.5
N4—O6—Zn1123.50 (16)C11—C10—H10A110.5
Zn1—O9—H9A109.5O1—C10—H10B110.5
Zn1—O9—H9B135.6C11—C10—H10B110.5
H9A—O9—H9B114.8H10A—C10—H10B108.7
C1—N1—C9118.3 (2)O2—C11—N2124.8 (2)
C1—N1—Zn1123.78 (16)O2—C11—C10121.6 (2)
C9—N1—Zn1117.69 (14)N2—C11—C10113.54 (19)
C11—N2—C12129.5 (2)C17—C12—C13120.1 (2)
C11—N2—H2115.3C17—C12—N2123.6 (2)
C12—N2—H2115.3C13—C12—N2116.3 (2)
O5—N3—O4122.1 (2)C12—C13—C14120.1 (3)
O5—N3—O3120.4 (2)C12—C13—H13120.0
O4—N3—O3117.5 (2)C14—C13—H13120.0
O7—N4—O8123.7 (2)C15—C14—C13120.1 (3)
O7—N4—O6119.6 (2)C15—C14—H14120.0
O8—N4—O6116.7 (2)C13—C14—H14120.0
N1—C1—C2122.5 (3)C14—C15—C16119.7 (3)
N1—C1—H1118.7C14—C15—H15120.1
C2—C1—H1118.7C16—C15—H15120.1
C3—C2—C1119.7 (3)C15—C16—C17121.1 (3)
C3—C2—H2A120.2C15—C16—H16119.5
C1—C2—H2A120.2C17—C16—H16119.5
C2—C3—C4120.1 (2)C16—C17—C12119.0 (3)
C2—C3—H3119.9C16—C17—H17120.5
C4—C3—H3119.9C12—C17—H17120.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O9—H9A···O6i0.821.992.803 (3)173
O9—H9B···O4ii0.881.972.797 (3)155
N2—H2···O8iii0.862.072.869 (3)155

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y, z; (iii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2270).

References

  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cai, Z.-H. & Tan, M.-Y. (2002). J. Rare Earths, 20, 382–384.
  • Li, X.-M., Wen, Y.-H., Li, M.-J. & Zhang, S.-S. (2005). Acta Cryst. E61, o2389–o2390.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, W.-N., Yuan, W.-B., Tang, N., Yang, R.-D., Yan, L. & Xu, Z.-H. (2006). Spectrochim. Acta A, 65, 912–918. [PubMed]

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