Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036756/ci2416sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036756/ci2416Isup2.hkl |
CCDC reference: 660049
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.093
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
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) 1.98
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The ligand 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (L) was synthesized according to the method reported in the literature (Zhang et al., 2005). A solution of ZnCl2 (0.1 mmol) in methanol (15 ml) was added to L (0.1 mmol). A yellow solid formed was filtered off and the resulting solution was kept at room temperature. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent after several days (yield: 30%). Analysis calculated for (C19H15ZnCl2N3): C 54.12, H 3.59, N 9.97%; found: C 54.26, H 3.44, N 10.11%.
H atoms were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 (aromatic) or 0.97 Å (methylene) and Uiso(H) = 1.2Ueq(C).
In recent years, much attention has been focused on the synthetic approach and the structural control of metal-organic coordination architectures with ligands based on pyrazolyl-pyridine chelating units (Steel et al., 2005; Ward et al., 2001). Many novel functional complexes with 3-(2-pyridyl)pyrazole and/or 3-(2-pyridyl)pyrazole ligands have been reported (Bell et al., 2003; Paul et al., 2004; Ward et al., 2001). Recently, we have reported the preparation of a non-planar flexible ligand, 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (L) (Zhang et al., 2005). Now we report here the crystal structure of a zinc(II) complex of this ligand, [Zn(L)Cl2], the title compound.
In the title compound, the ZnII center is four-coordinated by two N donors from one L ligand and two Cl- anions (Table 1). The coordination geometry around the ZnII center can be described as a distorted tetrahedron (Fig. 1).
In the crystal structure, the ZnII mononuclear units at (x, y, z) and (-x, -y, -z) are interconnected to form a dimer through π-π stacking interactions between the adjacent pyridine and pyrazole rings of the L ligand, with their centroids separated by 3.5166 (19) Å. The dimers are linked to form a chain along the a axis by C—H···π interactions (Table 2) involving the C2—C6/C11 (centroid Cg1) and C6—C11 (centroid Cg2) benzene rings of the L ligand (Fig. 2).
For synthesis, see: Zhang et al. (2005). For related literature, see: Bell et al. (2003); Paul et al. (2004); Steel (2005); Ward et al. (2001).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
[ZnCl2(C19H15N3)] | F(000) = 856 |
Mr = 421.61 | Dx = 1.559 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3039 reflections |
a = 12.069 (2) Å | θ = 2.3–25.2° |
b = 10.9474 (18) Å | µ = 1.67 mm−1 |
c = 13.609 (2) Å | T = 293 K |
β = 92.662 (3)° | Block, yellow |
V = 1796.1 (5) Å3 | 0.24 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3673 independent reflections |
Radiation source: fine-focus sealed tube | 2533 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −15→14 |
Tmin = 0.731, Tmax = 0.776 | k = −9→13 |
10232 measured reflections | l = −17→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.4714P] where P = (Fo2 + 2Fc2)/3 |
3673 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
[ZnCl2(C19H15N3)] | V = 1796.1 (5) Å3 |
Mr = 421.61 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.069 (2) Å | µ = 1.67 mm−1 |
b = 10.9474 (18) Å | T = 293 K |
c = 13.609 (2) Å | 0.24 × 0.20 × 0.18 mm |
β = 92.662 (3)° |
Bruker SMART CCD area-detector diffractometer | 3673 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2533 reflections with I > 2σ(I) |
Tmin = 0.731, Tmax = 0.776 | Rint = 0.046 |
10232 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.46 e Å−3 |
3673 reflections | Δρmin = −0.41 e Å−3 |
226 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 > 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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.11994 (3) | 0.26266 (3) | 0.11428 (2) | 0.03872 (13) | |
Cl1 | 0.05436 (8) | 0.22829 (10) | 0.25927 (7) | 0.0695 (3) | |
Cl2 | 0.20707 (8) | 0.43809 (7) | 0.10055 (6) | 0.0578 (2) | |
N1 | 0.29477 (18) | 0.0502 (2) | 0.06734 (18) | 0.0383 (6) | |
N2 | 0.20198 (18) | 0.1170 (2) | 0.05350 (17) | 0.0337 (5) | |
N3 | 0.01157 (18) | 0.2225 (2) | −0.00402 (17) | 0.0374 (6) | |
C1 | 0.3734 (2) | 0.0719 (3) | 0.1492 (2) | 0.0430 (7) | |
H1A | 0.4103 | −0.0042 | 0.1669 | 0.052* | |
H1B | 0.3335 | 0.0990 | 0.2055 | 0.052* | |
C2 | 0.4602 (2) | 0.1669 (3) | 0.1263 (2) | 0.0353 (6) | |
C3 | 0.4487 (3) | 0.2406 (3) | 0.0461 (2) | 0.0460 (8) | |
H3 | 0.3860 | 0.2327 | 0.0042 | 0.055* | |
C4 | 0.5288 (3) | 0.3285 (3) | 0.0250 (3) | 0.0554 (9) | |
H4 | 0.5186 | 0.3782 | −0.0301 | 0.066* | |
C5 | 0.6204 (3) | 0.3410 (3) | 0.0844 (3) | 0.0557 (9) | |
H5 | 0.6729 | 0.3999 | 0.0703 | 0.067* | |
C6 | 0.6377 (2) | 0.2655 (3) | 0.1679 (2) | 0.0461 (8) | |
C7 | 0.7348 (3) | 0.2733 (4) | 0.2298 (3) | 0.0634 (11) | |
H7 | 0.7889 | 0.3306 | 0.2160 | 0.076* | |
C8 | 0.7505 (3) | 0.1995 (4) | 0.3082 (3) | 0.0733 (13) | |
H8 | 0.8158 | 0.2047 | 0.3470 | 0.088* | |
C9 | 0.6694 (3) | 0.1152 (4) | 0.3315 (2) | 0.0648 (11) | |
H9 | 0.6803 | 0.0666 | 0.3872 | 0.078* | |
C10 | 0.5742 (3) | 0.1026 (3) | 0.2744 (2) | 0.0511 (8) | |
H10 | 0.5215 | 0.0450 | 0.2907 | 0.061* | |
C11 | 0.5558 (2) | 0.1775 (3) | 0.1901 (2) | 0.0383 (7) | |
C12 | 0.3038 (3) | −0.0296 (3) | −0.0065 (2) | 0.0491 (8) | |
H12 | 0.3614 | −0.0850 | −0.0132 | 0.059* | |
C13 | 0.2143 (3) | −0.0156 (3) | −0.0703 (2) | 0.0475 (8) | |
H13 | 0.1984 | −0.0585 | −0.1282 | 0.057* | |
C14 | 0.1521 (2) | 0.0764 (3) | −0.0301 (2) | 0.0348 (7) | |
C15 | 0.0460 (2) | 0.1310 (3) | −0.0620 (2) | 0.0359 (7) | |
C16 | −0.0163 (3) | 0.0922 (3) | −0.1437 (2) | 0.0472 (8) | |
H16 | 0.0084 | 0.0291 | −0.1829 | 0.057* | |
C17 | −0.1174 (3) | 0.1499 (3) | −0.1659 (2) | 0.0541 (9) | |
H17 | −0.1614 | 0.1253 | −0.2203 | 0.065* | |
C18 | −0.1514 (3) | 0.2421 (3) | −0.1078 (3) | 0.0553 (9) | |
H18 | −0.2187 | 0.2811 | −0.1219 | 0.066* | |
C19 | −0.0850 (2) | 0.2770 (3) | −0.0280 (3) | 0.0485 (8) | |
H19 | −0.1082 | 0.3411 | 0.0109 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0406 (2) | 0.0404 (2) | 0.0348 (2) | 0.00353 (16) | −0.00087 (14) | −0.00799 (16) |
Cl1 | 0.0731 (6) | 0.0930 (8) | 0.0437 (5) | −0.0062 (5) | 0.0168 (4) | −0.0042 (5) |
Cl2 | 0.0793 (6) | 0.0408 (5) | 0.0524 (5) | −0.0079 (4) | −0.0084 (4) | −0.0040 (4) |
N1 | 0.0338 (13) | 0.0375 (14) | 0.0440 (15) | 0.0029 (11) | 0.0055 (11) | −0.0011 (11) |
N2 | 0.0326 (12) | 0.0311 (13) | 0.0375 (13) | −0.0001 (10) | 0.0042 (10) | −0.0028 (10) |
N3 | 0.0336 (13) | 0.0432 (15) | 0.0353 (13) | −0.0015 (11) | −0.0005 (10) | 0.0008 (11) |
C1 | 0.0388 (17) | 0.0491 (19) | 0.0409 (17) | 0.0051 (14) | 0.0003 (14) | 0.0091 (14) |
C2 | 0.0321 (15) | 0.0385 (17) | 0.0356 (16) | 0.0067 (13) | 0.0036 (12) | −0.0018 (13) |
C3 | 0.0401 (17) | 0.051 (2) | 0.0463 (18) | 0.0010 (15) | −0.0032 (14) | 0.0073 (15) |
C4 | 0.064 (2) | 0.049 (2) | 0.053 (2) | −0.0014 (18) | 0.0043 (18) | 0.0124 (16) |
C5 | 0.057 (2) | 0.048 (2) | 0.063 (2) | −0.0116 (17) | 0.0121 (18) | −0.0066 (17) |
C6 | 0.0394 (17) | 0.051 (2) | 0.0480 (18) | 0.0022 (15) | 0.0041 (14) | −0.0226 (16) |
C7 | 0.046 (2) | 0.082 (3) | 0.062 (2) | −0.0041 (19) | 0.0001 (18) | −0.035 (2) |
C8 | 0.052 (2) | 0.108 (3) | 0.058 (3) | 0.020 (2) | −0.0153 (19) | −0.042 (2) |
C9 | 0.067 (2) | 0.087 (3) | 0.0384 (19) | 0.031 (2) | −0.0111 (18) | −0.0100 (18) |
C10 | 0.054 (2) | 0.061 (2) | 0.0379 (18) | 0.0166 (17) | −0.0013 (15) | −0.0043 (15) |
C11 | 0.0362 (16) | 0.0444 (18) | 0.0345 (16) | 0.0085 (14) | 0.0038 (13) | −0.0113 (13) |
C12 | 0.051 (2) | 0.0397 (19) | 0.057 (2) | 0.0072 (15) | 0.0144 (17) | −0.0105 (16) |
C13 | 0.061 (2) | 0.0406 (18) | 0.0415 (18) | −0.0003 (16) | 0.0081 (16) | −0.0126 (14) |
C14 | 0.0411 (16) | 0.0339 (16) | 0.0297 (14) | −0.0093 (13) | 0.0052 (13) | −0.0033 (12) |
C15 | 0.0399 (16) | 0.0370 (17) | 0.0306 (15) | −0.0126 (13) | 0.0009 (13) | 0.0030 (12) |
C16 | 0.060 (2) | 0.0465 (19) | 0.0340 (16) | −0.0136 (16) | −0.0032 (15) | 0.0026 (14) |
C17 | 0.055 (2) | 0.063 (2) | 0.0422 (19) | −0.0263 (18) | −0.0177 (16) | 0.0178 (18) |
C18 | 0.0400 (18) | 0.071 (3) | 0.054 (2) | −0.0074 (17) | −0.0097 (15) | 0.018 (2) |
C19 | 0.0384 (17) | 0.052 (2) | 0.055 (2) | 0.0029 (15) | −0.0005 (15) | 0.0057 (15) |
Zn1—N2 | 2.070 (2) | C6—C11 | 1.422 (4) |
Zn1—N3 | 2.074 (2) | C7—C8 | 1.345 (6) |
Zn1—Cl1 | 2.1924 (10) | C7—H7 | 0.93 |
Zn1—Cl2 | 2.2016 (9) | C8—C9 | 1.392 (5) |
N1—C12 | 1.340 (4) | C8—H8 | 0.93 |
N1—N2 | 1.344 (3) | C9—C10 | 1.363 (4) |
N1—C1 | 1.450 (3) | C9—H9 | 0.93 |
N2—C14 | 1.338 (3) | C10—C11 | 1.420 (4) |
N3—C19 | 1.337 (4) | C10—H10 | 0.93 |
N3—C15 | 1.352 (4) | C12—C13 | 1.363 (4) |
C1—C2 | 1.518 (4) | C12—H12 | 0.93 |
C1—H1A | 0.97 | C13—C14 | 1.384 (4) |
C1—H1B | 0.97 | C13—H13 | 0.93 |
C2—C3 | 1.359 (4) | C14—C15 | 1.461 (4) |
C2—C11 | 1.417 (4) | C15—C16 | 1.380 (4) |
C3—C4 | 1.404 (4) | C16—C17 | 1.395 (4) |
C3—H3 | 0.93 | C16—H16 | 0.93 |
C4—C5 | 1.345 (4) | C17—C18 | 1.358 (5) |
C4—H4 | 0.93 | C17—H17 | 0.93 |
C5—C6 | 1.413 (5) | C18—C19 | 1.374 (5) |
C5—H5 | 0.93 | C18—H18 | 0.93 |
C6—C7 | 1.414 (5) | C19—H19 | 0.93 |
N2—Zn1—N3 | 79.77 (9) | C6—C7—H7 | 119.4 |
N2—Zn1—Cl1 | 115.27 (7) | C7—C8—C9 | 120.3 (3) |
N3—Zn1—Cl1 | 114.91 (7) | C7—C8—H8 | 119.9 |
N2—Zn1—Cl2 | 113.51 (7) | C9—C8—H8 | 119.9 |
N3—Zn1—Cl2 | 113.93 (7) | C10—C9—C8 | 121.3 (4) |
Cl1—Zn1—Cl2 | 114.83 (4) | C10—C9—H9 | 119.3 |
C12—N1—N2 | 110.3 (2) | C8—C9—H9 | 119.3 |
C12—N1—C1 | 127.6 (3) | C9—C10—C11 | 119.9 (3) |
N2—N1—C1 | 122.0 (2) | C9—C10—H10 | 120.1 |
C14—N2—N1 | 106.1 (2) | C11—C10—H10 | 120.1 |
C14—N2—Zn1 | 113.01 (18) | C2—C11—C10 | 122.7 (3) |
N1—N2—Zn1 | 140.77 (18) | C2—C11—C6 | 118.7 (3) |
C19—N3—C15 | 118.5 (3) | C10—C11—C6 | 118.6 (3) |
C19—N3—Zn1 | 127.3 (2) | N1—C12—C13 | 108.3 (3) |
C15—N3—Zn1 | 114.23 (18) | N1—C12—H12 | 125.9 |
N1—C1—C2 | 112.8 (2) | C13—C12—H12 | 125.9 |
N1—C1—H1A | 109.0 | C12—C13—C14 | 105.0 (3) |
C2—C1—H1A | 109.0 | C12—C13—H13 | 127.5 |
N1—C1—H1B | 109.0 | C14—C13—H13 | 127.5 |
C2—C1—H1B | 109.0 | N2—C14—C13 | 110.3 (3) |
H1A—C1—H1B | 107.8 | N2—C14—C15 | 118.1 (2) |
C3—C2—C11 | 119.5 (3) | C13—C14—C15 | 131.6 (3) |
C3—C2—C1 | 121.8 (3) | N3—C15—C16 | 121.8 (3) |
C11—C2—C1 | 118.7 (2) | N3—C15—C14 | 114.7 (2) |
C2—C3—C4 | 121.7 (3) | C16—C15—C14 | 123.4 (3) |
C2—C3—H3 | 119.1 | C15—C16—C17 | 118.3 (3) |
C4—C3—H3 | 119.1 | C15—C16—H16 | 120.9 |
C5—C4—C3 | 120.1 (3) | C17—C16—H16 | 120.9 |
C5—C4—H4 | 119.9 | C18—C17—C16 | 119.7 (3) |
C3—C4—H4 | 119.9 | C18—C17—H17 | 120.2 |
C4—C5—C6 | 120.7 (3) | C16—C17—H17 | 120.2 |
C4—C5—H5 | 119.7 | C17—C18—C19 | 119.1 (3) |
C6—C5—H5 | 119.7 | C17—C18—H18 | 120.4 |
C5—C6—C7 | 122.1 (3) | C19—C18—H18 | 120.4 |
C5—C6—C11 | 119.3 (3) | N3—C19—C18 | 122.6 (3) |
C7—C6—C11 | 118.6 (3) | N3—C19—H19 | 118.7 |
C8—C7—C6 | 121.2 (4) | C18—C19—H19 | 118.7 |
C8—C7—H7 | 119.4 | ||
C12—N1—N2—C14 | 0.8 (3) | C3—C2—C11—C6 | −0.2 (4) |
C1—N1—N2—C14 | 177.3 (2) | C1—C2—C11—C6 | 179.3 (3) |
C12—N1—N2—Zn1 | −175.0 (2) | C9—C10—C11—C2 | 178.3 (3) |
C1—N1—N2—Zn1 | 1.6 (4) | C9—C10—C11—C6 | −0.6 (4) |
N3—Zn1—N2—C14 | 3.88 (18) | C5—C6—C11—C2 | 1.2 (4) |
Cl1—Zn1—N2—C14 | 116.72 (18) | C7—C6—C11—C2 | −177.9 (3) |
Cl2—Zn1—N2—C14 | −107.90 (18) | C5—C6—C11—C10 | −179.8 (3) |
N3—Zn1—N2—N1 | 179.4 (3) | C7—C6—C11—C10 | 1.1 (4) |
Cl1—Zn1—N2—N1 | −67.7 (3) | N2—N1—C12—C13 | −0.5 (3) |
Cl2—Zn1—N2—N1 | 67.7 (3) | C1—N1—C12—C13 | −176.8 (3) |
N2—Zn1—N3—C19 | 178.1 (3) | N1—C12—C13—C14 | 0.0 (3) |
Cl1—Zn1—N3—C19 | 64.9 (3) | N1—N2—C14—C13 | −0.8 (3) |
Cl2—Zn1—N3—C19 | −70.6 (2) | Zn1—N2—C14—C13 | 176.28 (19) |
N2—Zn1—N3—C15 | −2.49 (19) | N1—N2—C14—C15 | 178.2 (2) |
Cl1—Zn1—N3—C15 | −115.73 (18) | Zn1—N2—C14—C15 | −4.8 (3) |
Cl2—Zn1—N3—C15 | 108.82 (18) | C12—C13—C14—N2 | 0.5 (3) |
C12—N1—C1—C2 | 88.0 (4) | C12—C13—C14—C15 | −178.3 (3) |
N2—N1—C1—C2 | −87.9 (3) | C19—N3—C15—C16 | −0.9 (4) |
N1—C1—C2—C3 | 13.6 (4) | Zn1—N3—C15—C16 | 179.7 (2) |
N1—C1—C2—C11 | −166.0 (2) | C19—N3—C15—C14 | −179.8 (2) |
C11—C2—C3—C4 | −0.6 (5) | Zn1—N3—C15—C14 | 0.8 (3) |
C1—C2—C3—C4 | 179.9 (3) | N2—C14—C15—N3 | 2.7 (4) |
C2—C3—C4—C5 | 0.5 (5) | C13—C14—C15—N3 | −178.6 (3) |
C3—C4—C5—C6 | 0.6 (5) | N2—C14—C15—C16 | −176.2 (3) |
C4—C5—C6—C7 | 177.7 (3) | C13—C14—C15—C16 | 2.5 (5) |
C4—C5—C6—C11 | −1.4 (5) | N3—C15—C16—C17 | 0.0 (4) |
C5—C6—C7—C8 | −179.0 (3) | C14—C15—C16—C17 | 178.8 (3) |
C11—C6—C7—C8 | 0.1 (5) | C15—C16—C17—C18 | 0.4 (4) |
C6—C7—C8—C9 | −1.6 (5) | C16—C17—C18—C19 | 0.1 (5) |
C7—C8—C9—C10 | 2.1 (5) | C15—N3—C19—C18 | 1.4 (4) |
C8—C9—C10—C11 | −0.9 (5) | Zn1—N3—C19—C18 | −179.2 (2) |
C3—C2—C11—C10 | −179.2 (3) | C17—C18—C19—N3 | −1.0 (5) |
C1—C2—C11—C10 | 0.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.93 | 2.55 | 3.400 (4) | 152 |
C13—H13···Cg2i | 0.93 | 2.87 | 3.536 (3) | 129 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C19H15N3)] |
Mr | 421.61 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.069 (2), 10.9474 (18), 13.609 (2) |
β (°) | 92.662 (3) |
V (Å3) | 1796.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.67 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.731, 0.776 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10232, 3673, 2533 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.093, 1.02 |
No. of reflections | 3673 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.41 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL and PLATON (Spek, 2003).
Zn1—N2 | 2.070 (2) | Zn1—Cl1 | 2.1924 (10) |
Zn1—N3 | 2.074 (2) | Zn1—Cl2 | 2.2016 (9) |
N2—Zn1—N3 | 79.77 (9) | N2—Zn1—Cl2 | 113.51 (7) |
N2—Zn1—Cl1 | 115.27 (7) | N3—Zn1—Cl2 | 113.93 (7) |
N3—Zn1—Cl1 | 114.91 (7) | Cl1—Zn1—Cl2 | 114.83 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.93 | 2.55 | 3.400 (4) | 152 |
C13—H13···Cg2i | 0.93 | 2.87 | 3.536 (3) | 129 |
Symmetry code: (i) −x+1, −y, −z. |
In recent years, much attention has been focused on the synthetic approach and the structural control of metal-organic coordination architectures with ligands based on pyrazolyl-pyridine chelating units (Steel et al., 2005; Ward et al., 2001). Many novel functional complexes with 3-(2-pyridyl)pyrazole and/or 3-(2-pyridyl)pyrazole ligands have been reported (Bell et al., 2003; Paul et al., 2004; Ward et al., 2001). Recently, we have reported the preparation of a non-planar flexible ligand, 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (L) (Zhang et al., 2005). Now we report here the crystal structure of a zinc(II) complex of this ligand, [Zn(L)Cl2], the title compound.
In the title compound, the ZnII center is four-coordinated by two N donors from one L ligand and two Cl- anions (Table 1). The coordination geometry around the ZnII center can be described as a distorted tetrahedron (Fig. 1).
In the crystal structure, the ZnII mononuclear units at (x, y, z) and (-x, -y, -z) are interconnected to form a dimer through π-π stacking interactions between the adjacent pyridine and pyrazole rings of the L ligand, with their centroids separated by 3.5166 (19) Å. The dimers are linked to form a chain along the a axis by C—H···π interactions (Table 2) involving the C2—C6/C11 (centroid Cg1) and C6—C11 (centroid Cg2) benzene rings of the L ligand (Fig. 2).