Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047320/rk2047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047320/rk2047Isup2.hkl |
CCDC reference: 667105
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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%.
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# 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).
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).
[ZnCl2(C10H8N2)(C2H6OS)] | V = 750.7 (3) Å3 |
Mr = 370.61 | Z = 2 |
Triclinic, P1 | F(000) = 376 |
Hall symbol: -P 1 | Dx = 1.640 Mg m−3 |
a = 7.9553 (17) Å | Melting point: 593 K |
b = 9.5504 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 10.003 (2) Å | µ = 2.12 mm−1 |
α = 84.042 (16)° | T = 293 K |
β = 86.787 (17)° | Block, colourless |
γ = 83.798 (17)° | 0.5 × 0.5 × 0.45 mm |
Stoe IPDSII diffractometer | 3420 independent reflections |
Radiation source: fine–focus sealed tube | 3325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 0.15 pixels mm-1 | θmax = 27.9°, θmin = 2.1° |
ω scans | h = −10→8 |
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005) | k = −12→12 |
Tmin = 0.360, Tmax = 0.380 | l = −13→13 |
7002 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-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 reflections | Δρmax = 0.54 e Å−3 |
175 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.127 (11) |
[ZnCl2(C10H8N2)(C2H6OS)] | γ = 83.798 (17)° |
Mr = 370.61 | V = 750.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9553 (17) Å | Mo Kα radiation |
b = 9.5504 (19) Å | µ = 2.12 mm−1 |
c = 10.003 (2) Å | T = 293 K |
α = 84.042 (16)° | 0.5 × 0.5 × 0.45 mm |
β = 86.787 (17)° |
Stoe IPDSII diffractometer | 3420 independent reflections |
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005) | 3325 reflections with I > 2σ(I) |
Tmin = 0.360, Tmax = 0.380 | Rint = 0.046 |
7002 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.54 e Å−3 |
3420 reflections | Δρmin = −0.48 e Å−3 |
175 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4259 (3) | −0.0788 (2) | 0.2605 (2) | 0.0447 (4) | |
H1 | 0.4517 | −0.0535 | 0.1699 | 0.054* | |
C2 | 0.4984 (3) | −0.2067 (2) | 0.3198 (3) | 0.0540 (5) | |
H2 | 0.5710 | −0.2666 | 0.2700 | 0.065* | |
C3 | 0.4610 (3) | −0.2435 (2) | 0.4539 (3) | 0.0557 (6) | |
H3 | 0.5084 | −0.3289 | 0.4960 | 0.067* | |
C4 | 0.3527 (3) | −0.1527 (2) | 0.5255 (2) | 0.0473 (5) | |
H4 | 0.3259 | −0.1761 | 0.6162 | 0.057* | |
C5 | 0.2844 (2) | −0.02600 (18) | 0.45973 (18) | 0.0342 (3) | |
C6 | 0.1691 (2) | 0.07944 (19) | 0.52816 (17) | 0.0338 (3) | |
C7 | 0.1270 (3) | 0.0653 (2) | 0.6656 (2) | 0.0471 (5) | |
H7 | 0.1680 | −0.0149 | 0.7197 | 0.057* | |
C8 | 0.0234 (3) | 0.1726 (3) | 0.7201 (2) | 0.0545 (6) | |
H8 | −0.0066 | 0.1650 | 0.8116 | 0.065* | |
C9 | −0.0351 (3) | 0.2901 (3) | 0.6387 (2) | 0.0528 (5) | |
H9 | −0.1031 | 0.3641 | 0.6741 | 0.063* | |
C10 | 0.0094 (3) | 0.2960 (2) | 0.5028 (2) | 0.0466 (4) | |
H10 | −0.0317 | 0.3748 | 0.4470 | 0.056* | |
C11 | −0.2481 (3) | 0.5039 (2) | 0.1321 (3) | 0.0540 (5) | |
H11A | −0.1767 | 0.5631 | 0.1698 | 0.065* | |
H11B | −0.3323 | 0.4750 | 0.1988 | 0.065* | |
H11C | −0.3026 | 0.5557 | 0.0562 | 0.065* | |
C12 | −0.2877 (3) | 0.2621 (3) | 0.0277 (3) | 0.0559 (5) | |
H12A | −0.3768 | 0.2600 | 0.0965 | 0.067* | |
H12B | −0.2441 | 0.1670 | 0.0127 | 0.067* | |
H12C | −0.3313 | 0.3103 | −0.0541 | 0.067* | |
N1 | 0.32037 (19) | 0.00978 (16) | 0.32836 (16) | 0.0354 (3) | |
N2 | 0.1092 (2) | 0.19316 (16) | 0.44821 (15) | 0.0362 (3) | |
O1 | −0.06662 (18) | 0.26907 (18) | 0.21056 (15) | 0.0500 (4) | |
Zn1 | 0.19104 (2) | 0.20350 (2) | 0.238136 (19) | 0.03318 (11) | |
S1 | −0.12365 (6) | 0.35232 (5) | 0.07942 (5) | 0.03847 (13) | |
Cl1 | 0.32074 (7) | 0.40566 (5) | 0.23911 (6) | 0.04915 (15) | |
Cl2 | 0.23552 (10) | 0.13441 (6) | 0.02310 (5) | 0.06124 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0436 (10) | 0.0488 (10) | 0.0407 (10) | 0.0033 (8) | −0.0032 (8) | −0.0069 (8) |
C2 | 0.0479 (11) | 0.0471 (11) | 0.0662 (14) | 0.0107 (9) | −0.0106 (10) | −0.0135 (10) |
C3 | 0.0575 (13) | 0.0400 (10) | 0.0673 (15) | 0.0045 (9) | −0.0174 (11) | 0.0032 (10) |
C4 | 0.0534 (11) | 0.0442 (10) | 0.0432 (11) | −0.0069 (8) | −0.0113 (9) | 0.0085 (8) |
C5 | 0.0352 (8) | 0.0365 (8) | 0.0317 (8) | −0.0088 (6) | −0.0070 (6) | 0.0004 (6) |
C6 | 0.0350 (8) | 0.0402 (8) | 0.0280 (8) | −0.0122 (6) | −0.0032 (6) | −0.0016 (6) |
C7 | 0.0514 (11) | 0.0603 (12) | 0.0302 (9) | −0.0148 (9) | −0.0026 (8) | 0.0026 (8) |
C8 | 0.0534 (12) | 0.0832 (16) | 0.0305 (9) | −0.0173 (11) | 0.0039 (8) | −0.0144 (10) |
C9 | 0.0498 (11) | 0.0642 (13) | 0.0477 (12) | −0.0071 (10) | 0.0060 (9) | −0.0247 (10) |
C10 | 0.0523 (11) | 0.0443 (10) | 0.0431 (10) | −0.0017 (8) | 0.0016 (8) | −0.0094 (8) |
C11 | 0.0581 (13) | 0.0422 (10) | 0.0605 (14) | −0.0043 (9) | 0.0048 (10) | −0.0049 (9) |
C12 | 0.0603 (13) | 0.0563 (12) | 0.0531 (13) | −0.0065 (10) | −0.0126 (10) | −0.0101 (10) |
N1 | 0.0369 (7) | 0.0368 (7) | 0.0319 (7) | −0.0023 (6) | −0.0035 (6) | −0.0020 (6) |
N2 | 0.0406 (8) | 0.0377 (7) | 0.0303 (7) | −0.0055 (6) | 0.0006 (6) | −0.0033 (6) |
O1 | 0.0365 (7) | 0.0688 (10) | 0.0399 (8) | −0.0023 (6) | −0.0026 (6) | 0.0141 (7) |
Zn1 | 0.03600 (14) | 0.03394 (14) | 0.02856 (14) | −0.00156 (8) | −0.00143 (8) | −0.00035 (8) |
S1 | 0.0346 (2) | 0.0440 (2) | 0.0339 (2) | −0.00181 (17) | 0.00193 (16) | 0.00573 (17) |
Cl1 | 0.0550 (3) | 0.0430 (3) | 0.0505 (3) | −0.0150 (2) | 0.0055 (2) | −0.0035 (2) |
Cl2 | 0.0945 (5) | 0.0534 (3) | 0.0326 (3) | 0.0171 (3) | −0.0126 (3) | −0.0099 (2) |
C1—N1 | 1.335 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.383 (3) | C10—N2 | 1.337 (3) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.375 (4) | C11—S1 | 1.773 (2) |
C2—H2 | 0.9300 | C11—H11A | 0.9600 |
C3—C4 | 1.380 (3) | C11—H11B | 0.9600 |
C3—H3 | 0.9300 | C11—H11C | 0.9600 |
C4—C5 | 1.388 (3) | C12—S1 | 1.768 (2) |
C4—H4 | 0.9300 | C12—H12A | 0.9600 |
C5—N1 | 1.346 (2) | C12—H12B | 0.9600 |
C5—C6 | 1.482 (3) | C12—H12C | 0.9600 |
C6—N2 | 1.341 (2) | N1—Zn1 | 2.1546 (16) |
C6—C7 | 1.393 (3) | N2—Zn1 | 2.1604 (16) |
C7—C8 | 1.382 (3) | O1—S1 | 1.5268 (15) |
C7—H7 | 0.9300 | O1—Zn1 | 2.1024 (15) |
C8—C9 | 1.371 (4) | Zn1—Cl1 | 2.2863 (7) |
C8—H8 | 0.9300 | Zn1—Cl2 | 2.3123 (7) |
C9—C10 | 1.383 (3) | ||
N1—C1—C2 | 122.4 (2) | S1—C11—H11B | 109.5 |
N1—C1—H1 | 118.8 | H11A—C11—H11B | 109.5 |
C2—C1—H1 | 118.8 | S1—C11—H11C | 109.5 |
C3—C2—C1 | 118.7 (2) | H11A—C11—H11C | 109.5 |
C3—C2—H2 | 120.7 | H11B—C11—H11C | 109.5 |
C1—C2—H2 | 120.7 | S1—C12—H12A | 109.5 |
C2—C3—C4 | 119.53 (19) | S1—C12—H12B | 109.5 |
C2—C3—H3 | 120.2 | H12A—C12—H12B | 109.5 |
C4—C3—H3 | 120.2 | S1—C12—H12C | 109.5 |
C3—C4—C5 | 118.8 (2) | H12A—C12—H12C | 109.5 |
C3—C4—H4 | 120.6 | H12B—C12—H12C | 109.5 |
C5—C4—H4 | 120.6 | C1—N1—C5 | 118.86 (16) |
N1—C5—C4 | 121.69 (18) | C1—N1—Zn1 | 123.98 (13) |
N1—C5—C6 | 115.39 (15) | C5—N1—Zn1 | 117.07 (12) |
C4—C5—C6 | 122.92 (17) | C10—N2—C6 | 118.90 (17) |
N2—C6—C7 | 121.45 (18) | C10—N2—Zn1 | 123.67 (14) |
N2—C6—C5 | 115.02 (15) | C6—N2—Zn1 | 117.35 (12) |
C7—C6—C5 | 123.51 (17) | S1—O1—Zn1 | 120.57 (8) |
C8—C7—C6 | 118.8 (2) | O1—Zn1—N1 | 132.24 (6) |
C8—C7—H7 | 120.6 | O1—Zn1—N2 | 82.67 (6) |
C6—C7—H7 | 120.6 | N1—Zn1—N2 | 75.01 (6) |
C9—C8—C7 | 119.7 (2) | O1—Zn1—Cl1 | 106.16 (5) |
C9—C8—H8 | 120.2 | N1—Zn1—Cl1 | 117.33 (5) |
C7—C8—H8 | 120.2 | N2—Zn1—Cl1 | 95.19 (5) |
C8—C9—C10 | 118.4 (2) | O1—Zn1—Cl2 | 93.00 (5) |
C8—C9—H9 | 120.8 | N1—Zn1—Cl2 | 92.94 (5) |
C10—C9—H9 | 120.8 | N2—Zn1—Cl2 | 158.40 (5) |
N2—C10—C9 | 122.7 (2) | Cl1—Zn1—Cl2 | 106.32 (3) |
N2—C10—H10 | 118.6 | O1—S1—C12 | 105.02 (11) |
C9—C10—H10 | 118.6 | O1—S1—C11 | 104.08 (11) |
S1—C11—H11A | 109.5 | C12—S1—C11 | 98.71 (12) |
N1—C1—C2—C3 | −0.4 (3) | C7—C6—N2—Zn1 | 178.26 (14) |
C1—C2—C3—C4 | 0.1 (4) | C5—C6—N2—Zn1 | −0.48 (19) |
C2—C3—C4—C5 | −0.1 (3) | S1—O1—Zn1—N1 | −139.32 (10) |
C3—C4—C5—N1 | 0.4 (3) | S1—O1—Zn1—N2 | 158.65 (12) |
C3—C4—C5—C6 | −179.00 (19) | S1—O1—Zn1—Cl1 | 65.35 (12) |
N1—C5—C6—N2 | 3.3 (2) | S1—O1—Zn1—Cl2 | −42.60 (11) |
C4—C5—C6—N2 | −177.26 (17) | C1—N1—Zn1—O1 | 114.68 (16) |
N1—C5—C6—C7 | −175.40 (17) | C5—N1—Zn1—O1 | −61.81 (15) |
C4—C5—C6—C7 | 4.0 (3) | C1—N1—Zn1—N2 | 179.75 (17) |
N2—C6—C7—C8 | −1.1 (3) | C5—N1—Zn1—N2 | 3.26 (12) |
C5—C6—C7—C8 | 177.55 (18) | C1—N1—Zn1—Cl1 | −92.14 (16) |
C6—C7—C8—C9 | −0.2 (3) | C5—N1—Zn1—Cl1 | 91.37 (13) |
C7—C8—C9—C10 | 1.3 (3) | C1—N1—Zn1—Cl2 | 17.94 (16) |
C8—C9—C10—N2 | −1.2 (3) | C5—N1—Zn1—Cl2 | −158.55 (12) |
C2—C1—N1—C5 | 0.7 (3) | C10—N2—Zn1—O1 | −47.13 (17) |
C2—C1—N1—Zn1 | −175.75 (16) | C6—N2—Zn1—O1 | 136.01 (13) |
C4—C5—N1—C1 | −0.7 (3) | C10—N2—Zn1—N1 | 175.47 (17) |
C6—C5—N1—C1 | 178.77 (16) | C6—N2—Zn1—N1 | −1.38 (12) |
C4—C5—N1—Zn1 | 175.99 (14) | C10—N2—Zn1—Cl1 | 58.54 (16) |
C6—C5—N1—Zn1 | −4.56 (19) | C6—N2—Zn1—Cl1 | −118.31 (12) |
C9—C10—N2—C6 | −0.1 (3) | C10—N2—Zn1—Cl2 | −126.67 (16) |
C9—C10—N2—Zn1 | −176.92 (17) | C6—N2—Zn1—Cl2 | 56.5 (2) |
C7—C6—N2—C10 | 1.2 (3) | Zn1—O1—S1—C12 | 129.40 (13) |
C5—C6—N2—C10 | −177.49 (17) | Zn1—O1—S1—C11 | −127.36 (12) |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C10H8N2)(C2H6OS)] |
Mr | 370.61 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 750.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.12 |
Crystal size (mm) | 0.5 × 0.5 × 0.45 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Numerical (X-RED32; Stoe & Cie, 2005) |
Tmin, Tmax | 0.360, 0.380 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7002, 3420, 3325 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.080, 1.07 |
No. of reflections | 3420 |
No. of parameters | 175 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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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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).