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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m770.
Published online 2008 May 3. doi:  10.1107/S1600536808011793
PMCID: PMC2961423

(2-Meth­oxy-1,10-phenanthroline-κ2 N,N′)bis­(thio­cyanato-κN)zinc(II)

Abstract

In the title complex, [Zn(NCS)2(C13H10N2O)], the ZnII ion is in a distorted tetra­hdral ZnN2Cl2 coordination environment. In the crystal structure, there is a weak π–π stacking inter­action between adjacent 1,10-phenanthroline rings, with a pyridine centroid–centroid distance of 3.6620 (15) Å.

Related literature

For a related structure, see: Zhang et al. (2006 [triangle]). For related literature, see: McMorran & Steel (2002 [triangle]).

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Object name is e-64-0m770-scheme1.jpg

Experimental

Crystal data

  • [Zn(NCS)2(C13H10N2O)]
  • M r = 391.76
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m770-efi1.jpg
  • a = 26.360 (5) Å
  • b = 8.5949 (16) Å
  • c = 14.814 (3) Å
  • β = 96.266 (2)°
  • V = 3336.3 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.73 mm−1
  • T = 298 (2) K
  • 0.61 × 0.42 × 0.40 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.418, T max = 0.545 (expected range = 0.385–0.501)
  • 9311 measured reflections
  • 3616 independent reflections
  • 2974 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.097
  • S = 1.05
  • 3616 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011793/lh2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011793/lh2603Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Shandong Province of China for support (grant No. Y2007B26).

supplementary crystallographic information

Comment

Derivatives of 1,10-phenanthroline play a pivotal role in the area of modern coordination chemistry (e.g. Zhang et al. 2006 and important references cited within), but no structures of complexes with 2-methoxy-1,10-phenanthroline as a ligand have been reported. Herein we report the crystal structure of the title complex (I).

The molecular structure of (I) is shown in Fig. 1. In this mononuclear complex atom Zn1 is in a distorted tetrahedral coordination geometry (Table 1). In the crystal structure, there are weak π-π stacking interactions between symmetry related 1,10-phenanthroline ligands, with the relevant distances being Cg1···Cg1i = 3.6620 (15) Å and a perpendicular distance of 3.563 Å [symmetry code: (i) 1/2-x, 3/2-y, 1-z; Cg1 is the centroid of the N1/C1/C3/C4/C5/C15 ring].

Experimental

A methanol solution (15ml) of Zn(ClO4).6H2O (0.2951 g, 0.792 mmol) was added into a 10 ml methanol solution containing 2-methoxy-1,10-phenanthroline (0.1666 g, 0.792 mmol), and the mixture was stirred for a few minutes. Then a 10 ml methanol solution of NaSCN (0.1296 g, 1.60 mmol) was added to the above mixture. Yellow single crystals were obtained after the solution had been allowed to stand at room temperature for two weeks.

Refinement

H atoms were placed in calculated positions (C—H = 0.96 Å for methyl group and C—H = 0.93 Å for other H atoms) and refined as riding with Uiso = 1.5 Ueq(C) for methyl H and Uiso = 1.2 Ueq(C) for other H.

Figures

Fig. 1.
The molecular structure of (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.

Crystal data

[Zn(NCS)2(C13H10N2O)]F000 = 1584
Mr = 391.76Dx = 1.560 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4025 reflections
a = 26.360 (5) Åθ = 2.2–27.6º
b = 8.5949 (16) ŵ = 1.73 mm1
c = 14.814 (3) ÅT = 298 (2) K
β = 96.266 (2)ºBar, yellow
V = 3336.3 (10) Å30.61 × 0.42 × 0.40 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer3616 independent reflections
Radiation source: fine-focus sealed tube2974 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 298(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −33→26
Tmin = 0.418, Tmax = 0.545k = −9→10
9311 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0536P)2 + 0.2305P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3616 reflectionsΔρmax = 0.33 e Å3
209 parametersΔρmin = −0.49 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
Zn10.130923 (10)1.01266 (3)0.392499 (16)0.04081 (11)
S20.07232 (4)1.52220 (8)0.35198 (6)0.0700 (2)
S30.15576 (3)0.73246 (10)0.13159 (4)0.0627 (2)
N10.19776 (7)0.98293 (19)0.47711 (12)0.0374 (4)
N20.10343 (6)0.8750 (2)0.48692 (10)0.0372 (4)
C50.19054 (7)0.8893 (2)0.54870 (12)0.0350 (4)
N30.10454 (8)1.2204 (3)0.38239 (13)0.0557 (5)
O10.02497 (6)0.8745 (2)0.41868 (12)0.0593 (4)
C40.22974 (8)0.8481 (3)0.61569 (13)0.0415 (5)
C80.13985 (8)0.8311 (2)0.55315 (13)0.0363 (4)
C60.21868 (10)0.7477 (3)0.68714 (15)0.0510 (6)
H60.24460.72050.73200.061*
C120.05651 (8)0.8226 (3)0.48815 (15)0.0446 (5)
N40.13885 (8)0.9127 (3)0.27851 (13)0.0580 (5)
C140.14584 (8)0.8383 (3)0.21771 (14)0.0424 (5)
C90.13065 (9)0.7316 (3)0.62413 (15)0.0435 (5)
C20.09073 (8)1.3458 (3)0.37012 (13)0.0422 (5)
C70.17119 (10)0.6909 (3)0.69101 (15)0.0530 (6)
H70.16500.62440.73810.064*
C110.04328 (10)0.7227 (3)0.55773 (17)0.0552 (6)
H110.00990.68780.55800.066*
C30.27856 (9)0.9092 (3)0.60652 (16)0.0517 (6)
H30.30590.88540.64940.062*
C100.07972 (10)0.6789 (3)0.62360 (16)0.0545 (6)
H100.07130.61300.66950.065*
C150.28561 (10)1.0030 (3)0.53490 (19)0.0543 (7)
H150.31771.04350.52860.065*
C10.24425 (9)1.0379 (3)0.47095 (17)0.0471 (5)
H10.24951.10200.42230.057*
C13−0.02649 (9)0.8142 (4)0.4045 (2)0.0721 (8)
H13A−0.02540.70270.40120.108*
H13B−0.04330.85480.34870.108*
H13C−0.04490.84500.45400.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03960 (18)0.04250 (18)0.04019 (16)0.00072 (11)0.00369 (11)0.00223 (10)
S20.0862 (6)0.0478 (4)0.0775 (5)0.0193 (4)0.0155 (4)−0.0028 (3)
S30.0606 (4)0.0723 (5)0.0568 (4)0.0133 (3)0.0135 (3)−0.0126 (3)
N10.0323 (10)0.0394 (10)0.0409 (9)−0.0019 (7)0.0053 (7)−0.0012 (7)
N20.0320 (9)0.0377 (10)0.0427 (9)−0.0020 (8)0.0078 (7)−0.0029 (7)
C50.0357 (11)0.0319 (10)0.0383 (10)0.0010 (9)0.0080 (8)−0.0052 (8)
N30.0631 (14)0.0480 (13)0.0566 (12)0.0108 (11)0.0095 (10)0.0064 (9)
O10.0332 (9)0.0696 (12)0.0735 (11)−0.0053 (8)−0.0016 (7)0.0038 (9)
C40.0399 (12)0.0424 (12)0.0419 (11)0.0026 (10)0.0027 (9)−0.0043 (9)
C80.0378 (11)0.0344 (11)0.0380 (10)0.0001 (9)0.0099 (8)−0.0028 (8)
C60.0518 (15)0.0577 (15)0.0419 (12)0.0095 (12)−0.0021 (10)0.0045 (10)
C120.0355 (12)0.0456 (13)0.0533 (12)−0.0043 (10)0.0072 (9)−0.0080 (10)
N40.0637 (14)0.0639 (14)0.0467 (11)0.0039 (12)0.0065 (9)−0.0073 (11)
C140.0345 (11)0.0474 (13)0.0448 (12)0.0044 (10)0.0024 (9)0.0073 (10)
C90.0524 (14)0.0397 (12)0.0406 (11)−0.0023 (10)0.0145 (9)0.0000 (9)
C20.0395 (12)0.0512 (14)0.0369 (10)0.0001 (11)0.0089 (8)−0.0035 (9)
C70.0645 (17)0.0512 (15)0.0451 (12)0.0054 (12)0.0135 (11)0.0098 (11)
C110.0421 (13)0.0618 (16)0.0648 (15)−0.0143 (12)0.0205 (11)−0.0046 (12)
C30.0390 (12)0.0560 (15)0.0572 (13)0.0013 (11)−0.0072 (10)−0.0045 (12)
C100.0574 (15)0.0576 (15)0.0522 (13)−0.0120 (13)0.0220 (11)0.0036 (11)
C150.0366 (13)0.0585 (17)0.0672 (17)−0.0106 (11)0.0034 (12)−0.0008 (12)
C10.0373 (13)0.0486 (13)0.0561 (13)−0.0088 (11)0.0083 (10)0.0019 (10)
C130.0303 (13)0.086 (2)0.099 (2)−0.0058 (14)−0.0020 (13)−0.0092 (17)

Geometric parameters (Å, °)

Zn1—N31.916 (2)C6—C71.351 (3)
Zn1—N41.926 (2)C6—H60.9300
Zn1—N22.0254 (16)C12—C111.414 (3)
Zn1—N12.0636 (19)N4—C141.136 (3)
S2—C21.606 (3)C9—C101.416 (3)
S3—C141.611 (2)C9—C71.419 (3)
N1—C11.326 (3)C7—H70.9300
N1—C51.361 (3)C11—C101.346 (4)
N2—C121.319 (3)C11—H110.9300
N2—C81.349 (3)C3—C151.361 (4)
C5—C41.398 (3)C3—H30.9300
C5—C81.435 (3)C10—H100.9300
N3—C21.145 (3)C15—C11.397 (4)
O1—C121.328 (3)C15—H150.9300
O1—C131.446 (3)C1—H10.9300
C4—C31.410 (3)C13—H13A0.9600
C4—C61.421 (3)C13—H13B0.9600
C8—C91.397 (3)C13—H13C0.9600
N3—Zn1—N4114.85 (9)N4—C14—S3179.9 (3)
N3—Zn1—N2116.36 (8)C8—C9—C10115.7 (2)
N4—Zn1—N2115.23 (9)C8—C9—C7119.8 (2)
N3—Zn1—N1116.20 (8)C10—C9—C7124.5 (2)
N4—Zn1—N1108.07 (8)N3—C2—S2178.9 (2)
N2—Zn1—N181.62 (7)C6—C7—C9120.8 (2)
C1—N1—C5118.2 (2)C6—C7—H7119.6
C1—N1—Zn1130.42 (16)C9—C7—H7119.6
C5—N1—Zn1111.33 (14)C10—C11—C12119.0 (2)
C12—N2—C8119.23 (18)C10—C11—H11120.5
C12—N2—Zn1128.04 (15)C12—C11—H11120.5
C8—N2—Zn1112.68 (13)C15—C3—C4119.9 (2)
N1—C5—C4123.20 (19)C15—C3—H3120.0
N1—C5—C8116.87 (18)C4—C3—H3120.0
C4—C5—C8119.93 (18)C11—C10—C9121.0 (2)
C2—N3—Zn1174.4 (2)C11—C10—H10119.5
C12—O1—C13119.4 (2)C9—C10—H10119.5
C5—C4—C3116.7 (2)C3—C15—C1119.5 (2)
C5—C4—C6119.1 (2)C3—C15—H15120.2
C3—C4—C6124.2 (2)C1—C15—H15120.2
N2—C8—C9123.38 (19)N1—C1—C15122.4 (2)
N2—C8—C5117.48 (17)N1—C1—H1118.8
C9—C8—C5119.14 (19)C15—C1—H1118.8
C7—C6—C4121.2 (2)O1—C13—H13A109.5
C7—C6—H6119.4O1—C13—H13B109.5
C4—C6—H6119.4H13A—C13—H13B109.5
N2—C12—O1112.55 (19)O1—C13—H13C109.5
N2—C12—C11121.6 (2)H13A—C13—H13C109.5
O1—C12—C11125.8 (2)H13B—C13—H13C109.5
C14—N4—Zn1171.4 (2)
N3—Zn1—N1—C1−64.6 (2)C4—C5—C8—C9−1.0 (3)
N4—Zn1—N1—C166.2 (2)C5—C4—C6—C70.4 (3)
N2—Zn1—N1—C1−179.9 (2)C3—C4—C6—C7−178.8 (2)
N3—Zn1—N1—C5116.32 (14)C8—N2—C12—O1−179.57 (18)
N4—Zn1—N1—C5−112.90 (14)Zn1—N2—C12—O1−2.3 (3)
N2—Zn1—N1—C51.00 (13)C8—N2—C12—C110.7 (3)
N3—Zn1—N2—C1266.0 (2)Zn1—N2—C12—C11177.98 (16)
N4—Zn1—N2—C12−72.75 (19)C13—O1—C12—N2173.2 (2)
N1—Zn1—N2—C12−178.84 (19)C13—O1—C12—C11−7.1 (4)
N3—Zn1—N2—C8−116.55 (14)N2—C8—C9—C10−0.6 (3)
N4—Zn1—N2—C8104.70 (15)C5—C8—C9—C10−179.83 (19)
N1—Zn1—N2—C8−1.40 (13)N2—C8—C9—C7179.9 (2)
C1—N1—C5—C4−0.2 (3)C5—C8—C9—C70.6 (3)
Zn1—N1—C5—C4179.00 (16)C4—C6—C7—C9−0.7 (4)
C1—N1—C5—C8−179.68 (19)C8—C9—C7—C60.2 (4)
Zn1—N1—C5—C8−0.5 (2)C10—C9—C7—C6−179.3 (2)
N1—C5—C4—C30.2 (3)N2—C12—C11—C10−0.8 (4)
C8—C5—C4—C3179.70 (19)O1—C12—C11—C10179.5 (2)
N1—C5—C4—C6−178.99 (19)C5—C4—C3—C15−0.1 (3)
C8—C5—C4—C60.5 (3)C6—C4—C3—C15179.1 (2)
C12—N2—C8—C90.1 (3)C12—C11—C10—C90.2 (4)
Zn1—N2—C8—C9−177.64 (16)C8—C9—C10—C110.5 (3)
C12—N2—C8—C5179.27 (18)C7—C9—C10—C11180.0 (2)
Zn1—N2—C8—C51.6 (2)C4—C3—C15—C10.0 (4)
N1—C5—C8—N2−0.7 (3)C5—N1—C1—C150.1 (3)
C4—C5—C8—N2179.77 (18)Zn1—N1—C1—C15−178.98 (17)
N1—C5—C8—C9178.51 (17)C3—C15—C1—N10.1 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2603).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • McMorran, D. A. & Steel, P. J. (2002). Dalton Trans. pp. 3321–3326.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, J.-P., Lin, Y.-Y., Huang, X.-C. & Chen, X.-M. (2006). Eur. J. Inorg. Chem. pp. 3407–3412.

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