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metal-organic compounds
catena-Poly[[dichloridozinc(II)]-μ-1,4-bis(pyridin-2-ylmethoxy)benzene-κ2N:N′]
aDepartment of Materials and Chemistry Engineering, Heilongjiang Institute of Technology, Harbin 150050, People's Republic of China, bModern Analysis, Test and Research Center, Heilongjiang Institute of Science and Technology, Harbin 150027, People's Republic of China, and cCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
*Correspondence e-mail: hgf1000@163.com
In the title compound, [ZnCl2(C18H16N2O2)]n, the ZnII ion is tetrahedrally coordinated by two Cl atoms and by two N atoms from different 1,4-bis(pyridin-2-ylmethoxy)benzene ligands. The ligand shows a non-planar configuration, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.86 (12) and 70.74 (11)°. The flexible ligand coordinates to the ZnII ions, generating an infinite chain propagating along [001].
Related literature
For the synthesis and general background to flexible pyridyl-based ligands, see: Wang et al. (2007); Liu et al. (2010a
,b
)
Experimental
Crystal data
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536811035963/fj2447sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035963/fj2447Isup2.hkl
The 1,4-bis(pyridin-2-ylmethoxy)benzene ligand was synthesized as the reference method (Liu et al., 2010a,b). The title compound was produced by reaction of ZnCl2 (0.50 mmol,0.068 g) in water (5 mL) and 1,4-bis(pyridin-2-ylmethoxy)benzene (0.5 mmol, 0.146 g) in 5 mL methanol under constant stirring, and filtered after stirring for about one hour. The filtate was maintained for about one week under the room temperature to give colorless block-like crystals suitable for X-ray analysis.
The anormal reflection datas (4 -5 6), (-3 2 0) and (2 -3 1) have been omitted during the
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic); C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C).The metal-organic frameworks are determined by many factors, in which the organic ligands as building blocks and the kinds of metal ions are most important. Many pyridyl-containing ligands with strong coordination ability and functional characteristics have been studied over the recent years (Wang et al., 2007). The flexible bipyridyl ligands could react with transitional metals to construct the helical-like structures. Recently, as a continuration of previous works (Liu et al., 2010a, b), we report the
of the title compound here.In the title compound, [(ZnCl2)(C18H16N2O2)]n, each ZnII atom is four-coordinated by two Cl atoms and two N atoms from different 1,4-bis(pyridin-2-ylmethoxy)benzene ligands to form a distorted tetrahedral geometry configuration. The Zn-Cl bond lengths are 2.228 (1) and 2.253 (1) Å, and Zn-N bond lengths are 2.090 (2) and 2.080 (2) Å. The Cl(1)-Zn-Cl(2) bond angle (110.45 °) and the N(1)-Zn-N(2) bond angle (111.03 °) are nearly equal to 120 ° in order to minimize the
(Fig. 1, Table 1).The ligand is oriented in a divergent fashion, in which the dihedral angles between two terminal pyridine rings with the linking benzene ring are 7.86 (12) and 70.74 (11)°. In the crystal packing, the flexible ligands link the ZnII atoms to generate an infinite chain running along [001].
For the synthesis and general backround to flexible pyridyl-based ligands, see: Wang et al. (2007); Liu et al. (2010a,b)
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[ZnCl2(C18H16N2O2)] | Z = 2 |
Mr = 428.62 | F(000) = 436 |
Triclinic, P1 | Dx = 1.591 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8797 (18) Å | Cell parameters from 6941 reflections |
b = 10.458 (2) Å | θ = 3.6–27.5° |
c = 10.561 (2) Å | µ = 1.69 mm−1 |
α = 87.55 (3)° | T = 293 K |
β = 73.50 (3)° | Block, colorless |
γ = 72.31 (3)° | 0.21 × 0.19 × 0.17 mm |
V = 894.9 (3) Å3 |
Rigaku R-AXIS RAPID diffractometer | 4028 independent reflections |
Radiation source: fine-focus sealed tube | 3222 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scan | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→11 |
Tmin = 0.719, Tmax = 0.760 | k = −13→13 |
8755 measured reflections | l = −13→13 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0311P)2 + 0.1894P] where P = (Fo2 + 2Fc2)/3 |
4028 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
[ZnCl2(C18H16N2O2)] | γ = 72.31 (3)° |
Mr = 428.62 | V = 894.9 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.8797 (18) Å | Mo Kα radiation |
b = 10.458 (2) Å | µ = 1.69 mm−1 |
c = 10.561 (2) Å | T = 293 K |
α = 87.55 (3)° | 0.21 × 0.19 × 0.17 mm |
β = 73.50 (3)° |
Rigaku R-AXIS RAPID diffractometer | 4028 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3222 reflections with I > 2σ(I) |
Tmin = 0.719, Tmax = 0.760 | Rint = 0.028 |
8755 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.32 e Å−3 |
4028 reflections | Δρmin = −0.29 e Å−3 |
226 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.8929 (3) | 0.5157 (2) | 1.3377 (2) | 0.0426 (5) | |
H1 | 0.8933 | 0.5634 | 1.4099 | 0.051* | |
C2 | 0.9801 (3) | 0.3817 (2) | 1.3198 (3) | 0.0503 (6) | |
H2 | 1.0380 | 0.3394 | 1.3786 | 0.060* | |
C3 | 0.9800 (3) | 0.3111 (2) | 1.2128 (3) | 0.0508 (6) | |
H3 | 1.0393 | 0.2203 | 1.1976 | 0.061* | |
C4 | 0.8915 (3) | 0.3759 (2) | 1.1287 (2) | 0.0438 (6) | |
H4 | 0.8894 | 0.3293 | 1.0565 | 0.053* | |
C5 | 0.8052 (3) | 0.5115 (2) | 1.1526 (2) | 0.0331 (5) | |
C6 | 0.7058 (3) | 0.5875 (2) | 1.0652 (2) | 0.0369 (5) | |
H6A | 0.5895 | 0.6153 | 1.1133 | 0.044* | |
H6B | 0.7376 | 0.6674 | 1.0367 | 0.044* | |
C7 | 0.6566 (3) | 0.5573 (2) | 0.8599 (2) | 0.0377 (5) | |
C8 | 0.6904 (3) | 0.4718 (2) | 0.7515 (2) | 0.0415 (5) | |
H8 | 0.7590 | 0.3840 | 0.7478 | 0.050* | |
C9 | 0.6227 (3) | 0.5165 (2) | 0.6498 (2) | 0.0401 (5) | |
H9 | 0.6442 | 0.4583 | 0.5782 | 0.048* | |
C10 | 0.5228 (3) | 0.6472 (2) | 0.6532 (2) | 0.0353 (5) | |
C11 | 0.4855 (3) | 0.7321 (2) | 0.7619 (2) | 0.0438 (6) | |
H11 | 0.4157 | 0.8194 | 0.7658 | 0.053* | |
C12 | 0.5525 (3) | 0.6863 (2) | 0.8651 (2) | 0.0448 (6) | |
H12 | 0.5270 | 0.7432 | 0.9386 | 0.054* | |
C13 | 0.3676 (3) | 0.8196 (2) | 0.5444 (2) | 0.0373 (5) | |
H13A | 0.4243 | 0.8803 | 0.5609 | 0.045* | |
H13B | 0.2650 | 0.8351 | 0.6145 | 0.045* | |
C14 | 0.3322 (3) | 0.8458 (2) | 0.4139 (2) | 0.0325 (5) | |
C15 | 0.1734 (3) | 0.8713 (2) | 0.4044 (2) | 0.0396 (5) | |
H15 | 0.0900 | 0.8629 | 0.4778 | 0.047* | |
C16 | 0.1382 (3) | 0.9091 (2) | 0.2865 (3) | 0.0450 (6) | |
H16 | 0.0322 | 0.9250 | 0.2792 | 0.054* | |
C17 | 0.2624 (3) | 0.9227 (2) | 0.1811 (3) | 0.0460 (6) | |
H17 | 0.2419 | 0.9512 | 0.1013 | 0.055* | |
C18 | 0.4196 (3) | 0.8933 (2) | 0.1949 (2) | 0.0407 (5) | |
H18 | 0.5040 | 0.9021 | 0.1225 | 0.049* | |
Cl1 | 0.76914 (7) | 0.83611 (6) | 0.47450 (6) | 0.04153 (14) | |
Cl2 | 0.81884 (8) | 0.89409 (6) | 0.12085 (6) | 0.04904 (16) | |
N1 | 0.8066 (2) | 0.58173 (17) | 1.25574 (17) | 0.0322 (4) | |
N2 | 0.4562 (2) | 0.85272 (17) | 0.30782 (18) | 0.0329 (4) | |
O1 | 0.7344 (2) | 0.50350 (16) | 0.95442 (16) | 0.0488 (4) | |
O2 | 0.4678 (2) | 0.68394 (15) | 0.54293 (15) | 0.0416 (4) | |
Zn1 | 0.70586 (3) | 0.78909 (2) | 0.29601 (3) | 0.03361 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0489 (14) | 0.0418 (12) | 0.0389 (13) | −0.0072 (11) | −0.0224 (11) | 0.0025 (10) |
C2 | 0.0581 (16) | 0.0458 (14) | 0.0492 (16) | −0.0070 (12) | −0.0297 (13) | 0.0140 (12) |
C3 | 0.0563 (16) | 0.0348 (12) | 0.0540 (17) | −0.0014 (12) | −0.0184 (13) | 0.0058 (11) |
C4 | 0.0527 (14) | 0.0372 (12) | 0.0387 (14) | −0.0083 (11) | −0.0142 (11) | −0.0014 (10) |
C5 | 0.0334 (11) | 0.0354 (11) | 0.0295 (11) | −0.0095 (9) | −0.0089 (9) | 0.0034 (9) |
C6 | 0.0449 (13) | 0.0384 (11) | 0.0287 (12) | −0.0084 (10) | −0.0169 (10) | −0.0003 (9) |
C7 | 0.0503 (13) | 0.0351 (11) | 0.0323 (12) | −0.0120 (11) | −0.0201 (11) | 0.0018 (9) |
C8 | 0.0590 (15) | 0.0292 (11) | 0.0384 (13) | −0.0087 (11) | −0.0219 (12) | 0.0011 (9) |
C9 | 0.0594 (15) | 0.0318 (11) | 0.0343 (13) | −0.0152 (11) | −0.0192 (11) | −0.0026 (9) |
C10 | 0.0442 (13) | 0.0363 (11) | 0.0307 (12) | −0.0130 (10) | −0.0181 (10) | 0.0022 (9) |
C11 | 0.0543 (15) | 0.0378 (12) | 0.0378 (13) | −0.0029 (11) | −0.0218 (12) | −0.0034 (10) |
C12 | 0.0567 (15) | 0.0397 (12) | 0.0347 (13) | 0.0002 (11) | −0.0226 (12) | −0.0082 (10) |
C13 | 0.0384 (12) | 0.0391 (11) | 0.0310 (12) | −0.0038 (10) | −0.0127 (10) | −0.0028 (9) |
C14 | 0.0351 (11) | 0.0269 (10) | 0.0356 (12) | −0.0034 (9) | −0.0161 (10) | −0.0033 (8) |
C15 | 0.0367 (12) | 0.0382 (12) | 0.0448 (14) | −0.0080 (10) | −0.0164 (10) | −0.0017 (10) |
C16 | 0.0382 (13) | 0.0423 (13) | 0.0575 (16) | −0.0031 (11) | −0.0271 (12) | −0.0031 (11) |
C17 | 0.0532 (15) | 0.0444 (13) | 0.0433 (14) | −0.0020 (12) | −0.0321 (13) | 0.0031 (11) |
C18 | 0.0440 (13) | 0.0407 (12) | 0.0342 (13) | −0.0026 (11) | −0.0175 (11) | 0.0029 (10) |
Cl1 | 0.0482 (3) | 0.0434 (3) | 0.0426 (3) | −0.0150 (3) | −0.0264 (3) | 0.0013 (2) |
Cl2 | 0.0539 (4) | 0.0542 (3) | 0.0416 (3) | −0.0198 (3) | −0.0154 (3) | 0.0129 (3) |
N1 | 0.0331 (9) | 0.0344 (9) | 0.0291 (9) | −0.0069 (8) | −0.0127 (8) | 0.0033 (7) |
N2 | 0.0343 (9) | 0.0324 (9) | 0.0307 (10) | −0.0022 (8) | −0.0155 (8) | −0.0011 (7) |
O1 | 0.0704 (12) | 0.0377 (8) | 0.0383 (10) | −0.0005 (8) | −0.0320 (9) | −0.0043 (7) |
O2 | 0.0607 (10) | 0.0338 (8) | 0.0359 (9) | −0.0084 (8) | −0.0287 (8) | −0.0001 (6) |
Zn1 | 0.03523 (15) | 0.03499 (14) | 0.03301 (15) | −0.00713 (11) | −0.01731 (11) | 0.00198 (10) |
C1—N1 | 1.348 (3) | C11—C12 | 1.387 (3) |
C1—C2 | 1.371 (3) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—H12 | 0.9300 |
C2—C3 | 1.376 (4) | C13—O2 | 1.426 (3) |
C2—H2 | 0.9300 | C13—C14 | 1.495 (3) |
C3—C4 | 1.374 (3) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.387 (3) | C14—N2 | 1.346 (3) |
C4—H4 | 0.9300 | C14—C15 | 1.385 (3) |
C5—N1 | 1.344 (3) | C15—C16 | 1.381 (3) |
C5—C6 | 1.496 (3) | C15—H15 | 0.9300 |
C6—O1 | 1.410 (3) | C16—C17 | 1.364 (4) |
C6—H6A | 0.9700 | C16—H16 | 0.9300 |
C6—H6B | 0.9700 | C17—C18 | 1.384 (3) |
C7—C12 | 1.377 (3) | C17—H17 | 0.9300 |
C7—O1 | 1.378 (3) | C18—N2 | 1.341 (3) |
C7—C8 | 1.390 (3) | C18—H18 | 0.9300 |
C8—C9 | 1.373 (3) | Cl1—Zn1 | 2.2271 (7) |
C8—H8 | 0.9300 | Cl2—Zn1 | 2.2530 (10) |
C9—C10 | 1.380 (3) | N1—Zn1i | 2.0898 (18) |
C9—H9 | 0.9300 | N2—Zn1 | 2.0803 (18) |
C10—C11 | 1.381 (3) | Zn1—N1ii | 2.0898 (18) |
C10—O2 | 1.383 (3) | ||
N1—C1—C2 | 123.2 (2) | C7—C12—H12 | 119.7 |
N1—C1—H1 | 118.4 | C11—C12—H12 | 119.7 |
C2—C1—H1 | 118.4 | O2—C13—C14 | 109.20 (17) |
C1—C2—C3 | 118.5 (2) | O2—C13—H13A | 109.8 |
C1—C2—H2 | 120.8 | C14—C13—H13A | 109.8 |
C3—C2—H2 | 120.8 | O2—C13—H13B | 109.8 |
C4—C3—C2 | 119.4 (2) | C14—C13—H13B | 109.8 |
C4—C3—H3 | 120.3 | H13A—C13—H13B | 108.3 |
C2—C3—H3 | 120.3 | N2—C14—C15 | 120.9 (2) |
C3—C4—C5 | 119.4 (2) | N2—C14—C13 | 118.31 (19) |
C3—C4—H4 | 120.3 | C15—C14—C13 | 120.6 (2) |
C5—C4—H4 | 120.3 | C16—C15—C14 | 120.4 (2) |
N1—C5—C4 | 121.7 (2) | C16—C15—H15 | 119.8 |
N1—C5—C6 | 116.45 (18) | C14—C15—H15 | 119.8 |
C4—C5—C6 | 121.9 (2) | C17—C16—C15 | 118.5 (2) |
O1—C6—C5 | 108.69 (18) | C17—C16—H16 | 120.8 |
O1—C6—H6A | 110.0 | C15—C16—H16 | 120.8 |
C5—C6—H6A | 110.0 | C16—C17—C18 | 118.8 (2) |
O1—C6—H6B | 110.0 | C16—C17—H17 | 120.6 |
C5—C6—H6B | 110.0 | C18—C17—H17 | 120.6 |
H6A—C6—H6B | 108.3 | N2—C18—C17 | 123.1 (2) |
C12—C7—O1 | 125.3 (2) | N2—C18—H18 | 118.4 |
C12—C7—C8 | 119.3 (2) | C17—C18—H18 | 118.4 |
O1—C7—C8 | 115.4 (2) | C5—N1—C1 | 117.94 (18) |
C9—C8—C7 | 120.1 (2) | C5—N1—Zn1i | 127.03 (14) |
C9—C8—H8 | 119.9 | C1—N1—Zn1i | 114.79 (14) |
C7—C8—H8 | 119.9 | C18—N2—C14 | 118.08 (19) |
C8—C9—C10 | 120.5 (2) | C18—N2—Zn1 | 115.68 (15) |
C8—C9—H9 | 119.8 | C14—N2—Zn1 | 125.98 (14) |
C10—C9—H9 | 119.8 | C7—O1—C6 | 117.33 (17) |
C9—C10—C11 | 119.8 (2) | C10—O2—C13 | 116.16 (17) |
C9—C10—O2 | 115.81 (19) | N2—Zn1—N1ii | 111.05 (7) |
C11—C10—O2 | 124.4 (2) | N2—Zn1—Cl1 | 115.74 (6) |
C10—C11—C12 | 119.6 (2) | N1ii—Zn1—Cl1 | 107.18 (6) |
C10—C11—H11 | 120.2 | N2—Zn1—Cl2 | 103.67 (6) |
C12—C11—H11 | 120.2 | N1ii—Zn1—Cl2 | 108.57 (6) |
C7—C12—C11 | 120.6 (2) | Cl1—Zn1—Cl2 | 110.47 (3) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C18H16N2O2)] |
Mr | 428.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.8797 (18), 10.458 (2), 10.561 (2) |
α, β, γ (°) | 87.55 (3), 73.50 (3), 72.31 (3) |
V (Å3) | 894.9 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.69 |
Crystal size (mm) | 0.21 × 0.19 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.719, 0.760 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8755, 4028, 3222 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.073, 1.05 |
No. of reflections | 4028 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.29 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors thank the Educational Commission of Heilongjiang Province of China (project No. 12511472), Heilongjiang Institute of Technology and Heilongjiang University for supporting this work.
References
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The metal-organic frameworks are determined by many factors, in which the organic ligands as building blocks and the kinds of metal ions are most important. Many pyridyl-containing ligands with strong coordination ability and functional characteristics have been studied over the recent years (Wang et al., 2007). The flexible bipyridyl ligands could react with transitional metals to construct the helical-like structures. Recently, as a continuration of previous works (Liu et al., 2010a, b), we report the crystal structure of the title compound here.
In the title compound, [(ZnCl2)(C18H16N2O2)]n, each ZnII atom is four-coordinated by two Cl atoms and two N atoms from different 1,4-bis(pyridin-2-ylmethoxy)benzene ligands to form a distorted tetrahedral geometry configuration. The Zn-Cl bond lengths are 2.228 (1) and 2.253 (1) Å, and Zn-N bond lengths are 2.090 (2) and 2.080 (2) Å. The Cl(1)-Zn-Cl(2) bond angle (110.45 °) and the N(1)-Zn-N(2) bond angle (111.03 °) are nearly equal to 120 ° in order to minimize the steric hindrance (Fig. 1, Table 1).
The ligand is oriented in a divergent fashion, in which the dihedral angles between two terminal pyridine rings with the linking benzene ring are 7.86 (12) and 70.74 (11)°. In the crystal packing, the flexible ligands link the ZnII atoms to generate an infinite chain running along [001].