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In the title compound, [ZnCl2(C10H8N2)(C2H6OS)], the Zn atom is five-coordinate, forming a distorted trigonal–bipyramidal geometry involving one Cl atom, one dimethyl sulfoxide O atom and one 2,2′-bipyridine N atom in equatorial positions, with distances Zn—Cl = 2.2863 (7) Å, Zn—O = 2.1024 (15) Å and Zn—N = 2.1546 (16) Å. The axial positions are occupied by the other 2,2′-bipyridine N atom and a Cl atom, with distances N—Zn = 2.1604 (16) Å and Zn—Cl = 2.3123 (7) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047320/rk2047sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047320/rk2047Isup2.hkl
Contains datablock I

CCDC reference: 667105

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.079
  • Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.93 From the CIF: _diffrn_reflns_theta_full 27.93 From the CIF: _reflns_number_total 3420 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3609 Completeness (_total/calc) 94.76% PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.87
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The title compound, [ZnCl2(Bipy)(DMSO)] (I), has triclinic (P1) symmetry. The asymetric unit of (I) contains one monomeric five–coordinate zinc complex. The Zn atom is coordinated by one 2,2'–bipyridine ligand via both N atoms, two Cl- anions and one DMSO molecule via O atom. The complex exhibits a distorted trigonal bipyramidal geometry about the zinc atom, with atoms N2 and Cl2 in axial positions (Cl2—Zn1—N2 158.40 (5)°) and N1, Cl1 and O1 in equitorial positions. The Zn atom is 0.256 Å out of the equaitorial plane. The axial Zn—N and Zn—Cl bond lenghts are slightly longer than related equatorial bond lenghts. The Bipy ligand is slightly twisted, making an angle of 4.66° between the planes of two pyridine rings. The solid state of the molecule has a layer structure with the avrage distance of 3.397Å between 2,2'–bipyridins in closest layers. For related literature, see Lemoine et al. (2003) and Marjani et al. (2005).

Related literature top

For related literature, see: Lemoine et al. (2003); Marjani et al. (2005).

Experimental top

To a solution of ZnCl2 (0.136 g, 1 mmol) in freshly distilled ethanol (10 ml), was aded 2,2'–bipyridine (0.156 g, 1 mmol) and 2–mercaptopyridine (0.223 g, 2 mmol). The mixture was stirred under dinitrogen atmosphere for 4 h. Then resulted yellow suspension was filtered, washed with ethanol and dried in vacuo. The crude product was recrystalized from DMSO, yeild crystals of [ZnCl2(C10H8N2)(DMSO)], (0.28 g, 75.68%). M.p. = 593–598 K (decompose). Found: C, 38.66; H, 3.81; N, 6.75%. Calculated for C12H14Cl2N2OSZn: C, 38.89; H, 3.81; N, 7.56%.

Structure description top

?

# Following replaced by publCIF - Mon Sep 10 18:26:47 2007

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see (type here to add references to related literature).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the numbering scheme. Displacement ellipsoids drawn at the 50% probability level. H atoms are presented as a spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of (I), showing its layer structure.
(2,2'-Bipyridine-κ2N,N')dichlorido(dimethyl sulfoxide-κO)zinc(II) top
Crystal data top
[ZnCl2(C10H8N2)(C2H6OS)]V = 750.7 (3) Å3
Mr = 370.61Z = 2
Triclinic, P1F(000) = 376
Hall symbol: -P 1Dx = 1.640 Mg m3
a = 7.9553 (17) ÅMelting point: 593 K
b = 9.5504 (19) ÅMo Kα radiation, λ = 0.71073 Å
c = 10.003 (2) ŵ = 2.12 mm1
α = 84.042 (16)°T = 293 K
β = 86.787 (17)°Block, colourless
γ = 83.798 (17)°0.5 × 0.5 × 0.45 mm
Data collection top
Stoe IPDSII
diffractometer
3420 independent reflections
Radiation source: fine–focus sealed tube3325 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 0.15 pixels mm-1θmax = 27.9°, θmin = 2.1°
ω scansh = 108
Absorption correction: numerical
(X-RED32; Stoe & Cie, 2005)
k = 1212
Tmin = 0.360, Tmax = 0.380l = 1313
7002 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2984P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.013
3420 reflectionsΔρmax = 0.54 e Å3
175 parametersΔρmin = 0.48 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.127 (11)
Crystal data top
[ZnCl2(C10H8N2)(C2H6OS)]γ = 83.798 (17)°
Mr = 370.61V = 750.7 (3) Å3
Triclinic, P1Z = 2
a = 7.9553 (17) ÅMo Kα radiation
b = 9.5504 (19) ŵ = 2.12 mm1
c = 10.003 (2) ÅT = 293 K
α = 84.042 (16)°0.5 × 0.5 × 0.45 mm
β = 86.787 (17)°
Data collection top
Stoe IPDSII
diffractometer
3420 independent reflections
Absorption correction: numerical
(X-RED32; Stoe & Cie, 2005)
3325 reflections with I > 2σ(I)
Tmin = 0.360, Tmax = 0.380Rint = 0.046
7002 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.07Δρmax = 0.54 e Å3
3420 reflectionsΔρmin = 0.48 e Å3
175 parameters
Special details top

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 > 2σ(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) top
xyzUiso*/Ueq
C10.4259 (3)0.0788 (2)0.2605 (2)0.0447 (4)
H10.45170.05350.16990.054*
C20.4984 (3)0.2067 (2)0.3198 (3)0.0540 (5)
H20.57100.26660.27000.065*
C30.4610 (3)0.2435 (2)0.4539 (3)0.0557 (6)
H30.50840.32890.49600.067*
C40.3527 (3)0.1527 (2)0.5255 (2)0.0473 (5)
H40.32590.17610.61620.057*
C50.2844 (2)0.02600 (18)0.45973 (18)0.0342 (3)
C60.1691 (2)0.07944 (19)0.52816 (17)0.0338 (3)
C70.1270 (3)0.0653 (2)0.6656 (2)0.0471 (5)
H70.16800.01490.71970.057*
C80.0234 (3)0.1726 (3)0.7201 (2)0.0545 (6)
H80.00660.16500.81160.065*
C90.0351 (3)0.2901 (3)0.6387 (2)0.0528 (5)
H90.10310.36410.67410.063*
C100.0094 (3)0.2960 (2)0.5028 (2)0.0466 (4)
H100.03170.37480.44700.056*
C110.2481 (3)0.5039 (2)0.1321 (3)0.0540 (5)
H11A0.17670.56310.16980.065*
H11B0.33230.47500.19880.065*
H11C0.30260.55570.05620.065*
C120.2877 (3)0.2621 (3)0.0277 (3)0.0559 (5)
H12A0.37680.26000.09650.067*
H12B0.24410.16700.01270.067*
H12C0.33130.31030.05410.067*
N10.32037 (19)0.00978 (16)0.32836 (16)0.0354 (3)
N20.1092 (2)0.19316 (16)0.44821 (15)0.0362 (3)
O10.06662 (18)0.26907 (18)0.21056 (15)0.0500 (4)
Zn10.19104 (2)0.20350 (2)0.238136 (19)0.03318 (11)
S10.12365 (6)0.35232 (5)0.07942 (5)0.03847 (13)
Cl10.32074 (7)0.40566 (5)0.23911 (6)0.04915 (15)
Cl20.23552 (10)0.13441 (6)0.02310 (5)0.06124 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0436 (10)0.0488 (10)0.0407 (10)0.0033 (8)0.0032 (8)0.0069 (8)
C20.0479 (11)0.0471 (11)0.0662 (14)0.0107 (9)0.0106 (10)0.0135 (10)
C30.0575 (13)0.0400 (10)0.0673 (15)0.0045 (9)0.0174 (11)0.0032 (10)
C40.0534 (11)0.0442 (10)0.0432 (11)0.0069 (8)0.0113 (9)0.0085 (8)
C50.0352 (8)0.0365 (8)0.0317 (8)0.0088 (6)0.0070 (6)0.0004 (6)
C60.0350 (8)0.0402 (8)0.0280 (8)0.0122 (6)0.0032 (6)0.0016 (6)
C70.0514 (11)0.0603 (12)0.0302 (9)0.0148 (9)0.0026 (8)0.0026 (8)
C80.0534 (12)0.0832 (16)0.0305 (9)0.0173 (11)0.0039 (8)0.0144 (10)
C90.0498 (11)0.0642 (13)0.0477 (12)0.0071 (10)0.0060 (9)0.0247 (10)
C100.0523 (11)0.0443 (10)0.0431 (10)0.0017 (8)0.0016 (8)0.0094 (8)
C110.0581 (13)0.0422 (10)0.0605 (14)0.0043 (9)0.0048 (10)0.0049 (9)
C120.0603 (13)0.0563 (12)0.0531 (13)0.0065 (10)0.0126 (10)0.0101 (10)
N10.0369 (7)0.0368 (7)0.0319 (7)0.0023 (6)0.0035 (6)0.0020 (6)
N20.0406 (8)0.0377 (7)0.0303 (7)0.0055 (6)0.0006 (6)0.0033 (6)
O10.0365 (7)0.0688 (10)0.0399 (8)0.0023 (6)0.0026 (6)0.0141 (7)
Zn10.03600 (14)0.03394 (14)0.02856 (14)0.00156 (8)0.00143 (8)0.00035 (8)
S10.0346 (2)0.0440 (2)0.0339 (2)0.00181 (17)0.00193 (16)0.00573 (17)
Cl10.0550 (3)0.0430 (3)0.0505 (3)0.0150 (2)0.0055 (2)0.0035 (2)
Cl20.0945 (5)0.0534 (3)0.0326 (3)0.0171 (3)0.0126 (3)0.0099 (2)
Geometric parameters (Å, º) top
C1—N11.335 (3)C9—H90.9300
C1—C21.383 (3)C10—N21.337 (3)
C1—H10.9300C10—H100.9300
C2—C31.375 (4)C11—S11.773 (2)
C2—H20.9300C11—H11A0.9600
C3—C41.380 (3)C11—H11B0.9600
C3—H30.9300C11—H11C0.9600
C4—C51.388 (3)C12—S11.768 (2)
C4—H40.9300C12—H12A0.9600
C5—N11.346 (2)C12—H12B0.9600
C5—C61.482 (3)C12—H12C0.9600
C6—N21.341 (2)N1—Zn12.1546 (16)
C6—C71.393 (3)N2—Zn12.1604 (16)
C7—C81.382 (3)O1—S11.5268 (15)
C7—H70.9300O1—Zn12.1024 (15)
C8—C91.371 (4)Zn1—Cl12.2863 (7)
C8—H80.9300Zn1—Cl22.3123 (7)
C9—C101.383 (3)
N1—C1—C2122.4 (2)S1—C11—H11B109.5
N1—C1—H1118.8H11A—C11—H11B109.5
C2—C1—H1118.8S1—C11—H11C109.5
C3—C2—C1118.7 (2)H11A—C11—H11C109.5
C3—C2—H2120.7H11B—C11—H11C109.5
C1—C2—H2120.7S1—C12—H12A109.5
C2—C3—C4119.53 (19)S1—C12—H12B109.5
C2—C3—H3120.2H12A—C12—H12B109.5
C4—C3—H3120.2S1—C12—H12C109.5
C3—C4—C5118.8 (2)H12A—C12—H12C109.5
C3—C4—H4120.6H12B—C12—H12C109.5
C5—C4—H4120.6C1—N1—C5118.86 (16)
N1—C5—C4121.69 (18)C1—N1—Zn1123.98 (13)
N1—C5—C6115.39 (15)C5—N1—Zn1117.07 (12)
C4—C5—C6122.92 (17)C10—N2—C6118.90 (17)
N2—C6—C7121.45 (18)C10—N2—Zn1123.67 (14)
N2—C6—C5115.02 (15)C6—N2—Zn1117.35 (12)
C7—C6—C5123.51 (17)S1—O1—Zn1120.57 (8)
C8—C7—C6118.8 (2)O1—Zn1—N1132.24 (6)
C8—C7—H7120.6O1—Zn1—N282.67 (6)
C6—C7—H7120.6N1—Zn1—N275.01 (6)
C9—C8—C7119.7 (2)O1—Zn1—Cl1106.16 (5)
C9—C8—H8120.2N1—Zn1—Cl1117.33 (5)
C7—C8—H8120.2N2—Zn1—Cl195.19 (5)
C8—C9—C10118.4 (2)O1—Zn1—Cl293.00 (5)
C8—C9—H9120.8N1—Zn1—Cl292.94 (5)
C10—C9—H9120.8N2—Zn1—Cl2158.40 (5)
N2—C10—C9122.7 (2)Cl1—Zn1—Cl2106.32 (3)
N2—C10—H10118.6O1—S1—C12105.02 (11)
C9—C10—H10118.6O1—S1—C11104.08 (11)
S1—C11—H11A109.5C12—S1—C1198.71 (12)
N1—C1—C2—C30.4 (3)C7—C6—N2—Zn1178.26 (14)
C1—C2—C3—C40.1 (4)C5—C6—N2—Zn10.48 (19)
C2—C3—C4—C50.1 (3)S1—O1—Zn1—N1139.32 (10)
C3—C4—C5—N10.4 (3)S1—O1—Zn1—N2158.65 (12)
C3—C4—C5—C6179.00 (19)S1—O1—Zn1—Cl165.35 (12)
N1—C5—C6—N23.3 (2)S1—O1—Zn1—Cl242.60 (11)
C4—C5—C6—N2177.26 (17)C1—N1—Zn1—O1114.68 (16)
N1—C5—C6—C7175.40 (17)C5—N1—Zn1—O161.81 (15)
C4—C5—C6—C74.0 (3)C1—N1—Zn1—N2179.75 (17)
N2—C6—C7—C81.1 (3)C5—N1—Zn1—N23.26 (12)
C5—C6—C7—C8177.55 (18)C1—N1—Zn1—Cl192.14 (16)
C6—C7—C8—C90.2 (3)C5—N1—Zn1—Cl191.37 (13)
C7—C8—C9—C101.3 (3)C1—N1—Zn1—Cl217.94 (16)
C8—C9—C10—N21.2 (3)C5—N1—Zn1—Cl2158.55 (12)
C2—C1—N1—C50.7 (3)C10—N2—Zn1—O147.13 (17)
C2—C1—N1—Zn1175.75 (16)C6—N2—Zn1—O1136.01 (13)
C4—C5—N1—C10.7 (3)C10—N2—Zn1—N1175.47 (17)
C6—C5—N1—C1178.77 (16)C6—N2—Zn1—N11.38 (12)
C4—C5—N1—Zn1175.99 (14)C10—N2—Zn1—Cl158.54 (16)
C6—C5—N1—Zn14.56 (19)C6—N2—Zn1—Cl1118.31 (12)
C9—C10—N2—C60.1 (3)C10—N2—Zn1—Cl2126.67 (16)
C9—C10—N2—Zn1176.92 (17)C6—N2—Zn1—Cl256.5 (2)
C7—C6—N2—C101.2 (3)Zn1—O1—S1—C12129.40 (13)
C5—C6—N2—C10177.49 (17)Zn1—O1—S1—C11127.36 (12)

Experimental details

Crystal data
Chemical formula[ZnCl2(C10H8N2)(C2H6OS)]
Mr370.61
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.9553 (17), 9.5504 (19), 10.003 (2)
α, β, γ (°)84.042 (16), 86.787 (17), 83.798 (17)
V3)750.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.12
Crystal size (mm)0.5 × 0.5 × 0.45
Data collection
DiffractometerStoe IPDSII
Absorption correctionNumerical
(X-RED32; Stoe & Cie, 2005)
Tmin, Tmax0.360, 0.380
No. of measured, independent and
observed [I > 2σ(I)] reflections
7002, 3420, 3325
Rint0.046
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.080, 1.07
No. of reflections3420
No. of parameters175
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.48

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

 

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