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metal-organic compounds
catena-Poly[[dichloridomercury(II)]-μ-1,4-bis[(pyridin-2-yl)methoxy]benzene-κ2N:N′]
aDepartment of Materials and Chemical 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, [HgCl2(C18H16N2O2)]n, the HgII atom is four-coordinated in a distorted tetrahedral environment defined by two Cl atoms and two N atoms from two 1,4-bis(pyridin-2-ylmethoxy)benzene ligands. The ligand shows a non-coplanar conformation, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.275 (17) and 74.020 (14)°. The flexible ligands link the HgII atoms into a chain running along [010], with an Hg⋯Hg separation of 10.335 (5) Å, which is equal to the b axis. The chains are connected by C—H⋯O and C—H⋯Cl hydrogen bonds.
Related literature
For the synthesis of the ligand and general background to flexible pyridyl-based ligands, see: Liu et al. (2010a,b
); Wang et al. (2007
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: DIAMOND (Brandenburg, 1999
); software used to prepare material for publication: SHELXTL (Sheldrick, 2008
).
Supporting information
https://doi.org/10.1107/S1600536811038323/hy2469sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038323/hy2469Isup2.hkl
1,4-Bis(pyridin-2-ylmethoxy)benzene was synthesized as the literature method (Liu et al., 2010a,b). The title compound was produced by the 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 methanol (5 ml) under constant stirring. The mixture was filtered after stirring for about one hour. The filtate was maintained for about one week at room temperature to give colorless block-like crystals suitable for X-ray analysis.
The highest residual electron density was found at 0.87 Å from Hg1 atom and the deepest hole at 0.76 Å from Hg1 atom. H atoms were placed in calculated positions and treated as riding atoms, with C—H = 0.93 (aromatic) and 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 can react with transition metals to construct helical-like structures. Recently, as a continuation of previous studies (Liu et al., 2010a, b), we report here the
of the title compound.In the title compound, the HgII atom is four-coordinated by two Cl atoms and two N atoms from two 1,4-bis(pyridin-2-ylmethoxy)benzene ligands, forming a tetrahedral geometry (Fig. 1). The Hg—Cl bond lengths are 2.398 (2) and 2.452 (2) Å, and Hg—N bond lengths are 2.282 (5) and 2.411 (5) Å. The angles around the Hg atom are in a range of 100.63 (13)–122.30 (12)°. The ligand shows a noncoplanar conformation, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.275 (17) and 74.020 (14)°. In the crystal, the flexible ligands link the HgII atoms into a chain running along [0 1 0], with an Hg···Hg separation of 10.335 (5)Å, which is equal to the b axis of the
(Fig. 2). The chains are connected by C—H···O and C—H···Cl hydrogen bonds (Table 1).For the synthesis of the ligand and general background to flexible pyridyl-based ligands, see: Liu et al. (2010a,b); Wang et al. (2007).
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[HgCl2(C18H16N2O2)] | Z = 2 |
Mr = 563.82 | F(000) = 536 |
Triclinic, P1 | Dx = 2.027 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.201 (5) Å | Cell parameters from 8238 reflections |
b = 10.335 (5) Å | θ = 3.6–27.5° |
c = 11.040 (6) Å | µ = 8.63 mm−1 |
α = 86.11 (2)° | T = 293 K |
β = 66.51 (2)° | Block, colorless |
γ = 73.860 (18)° | 0.19 × 0.17 × 0.17 mm |
V = 923.8 (9) Å3 |
Rigaku R-AXIS RAPID diffractometer | 4179 independent reflections |
Radiation source: fine-focus sealed tube | 3688 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω scan | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→11 |
Tmin = 0.288, Tmax = 0.325 | k = −13→13 |
9080 measured reflections | l = −14→14 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3 |
4179 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 1.56 e Å−3 |
0 restraints | Δρmin = −1.74 e Å−3 |
[HgCl2(C18H16N2O2)] | γ = 73.860 (18)° |
Mr = 563.82 | V = 923.8 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.201 (5) Å | Mo Kα radiation |
b = 10.335 (5) Å | µ = 8.63 mm−1 |
c = 11.040 (6) Å | T = 293 K |
α = 86.11 (2)° | 0.19 × 0.17 × 0.17 mm |
β = 66.51 (2)° |
Rigaku R-AXIS RAPID diffractometer | 4179 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3688 reflections with I > 2σ(I) |
Tmin = 0.288, Tmax = 0.325 | Rint = 0.051 |
9080 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.16 | Δρmax = 1.56 e Å−3 |
4179 reflections | Δρmin = −1.74 e Å−3 |
226 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3961 (8) | 1.3384 (6) | 0.0220 (7) | 0.0444 (16) | |
H1 | 0.3896 | 1.4124 | 0.0692 | 0.053* | |
C2 | 0.5080 (10) | 1.3141 (7) | −0.1062 (7) | 0.0503 (18) | |
H2 | 0.5756 | 1.3705 | −0.1448 | 0.060* | |
C3 | 0.5187 (9) | 1.2054 (7) | −0.1767 (7) | 0.0505 (18) | |
H3 | 0.5939 | 1.1867 | −0.2640 | 0.061* | |
C4 | 0.4164 (9) | 1.1238 (7) | −0.1164 (7) | 0.0438 (15) | |
H4 | 0.4213 | 1.0497 | −0.1626 | 0.053* | |
C5 | 0.3057 (8) | 1.1542 (6) | 0.0148 (6) | 0.0343 (12) | |
C6 | 0.1907 (9) | 1.0703 (6) | 0.0877 (7) | 0.0414 (15) | |
H6A | 0.2040 | 1.0418 | 0.1691 | 0.050* | |
H6B | 0.0774 | 1.1229 | 0.1100 | 0.050* | |
C7 | 0.1385 (9) | 0.8632 (6) | 0.0600 (6) | 0.0370 (14) | |
C8 | 0.0193 (9) | 0.8735 (6) | 0.1867 (7) | 0.0468 (18) | |
H8 | −0.0110 | 0.9494 | 0.2412 | 0.056* | |
C9 | −0.0548 (9) | 0.7707 (6) | 0.2322 (7) | 0.0444 (16) | |
H9 | −0.1340 | 0.7771 | 0.3181 | 0.053* | |
C10 | −0.0126 (8) | 0.6587 (5) | 0.1515 (6) | 0.0321 (12) | |
C11 | 0.1058 (9) | 0.6489 (6) | 0.0227 (6) | 0.0407 (15) | |
H11 | 0.1345 | 0.5739 | −0.0326 | 0.049* | |
C12 | 0.1794 (9) | 0.7515 (7) | −0.0215 (7) | 0.0446 (16) | |
H12 | 0.2580 | 0.7457 | −0.1076 | 0.053* | |
C13 | −0.1985 (8) | 0.5549 (6) | 0.3153 (6) | 0.0374 (13) | |
H13A | −0.2948 | 0.6272 | 0.3208 | 0.045* | |
H13B | −0.1615 | 0.5746 | 0.3811 | 0.045* | |
C14 | −0.2419 (7) | 0.4243 (6) | 0.3415 (6) | 0.0324 (12) | |
C15 | −0.3957 (8) | 0.4143 (7) | 0.3561 (7) | 0.0401 (14) | |
H15 | −0.4710 | 0.4882 | 0.3417 | 0.048* | |
C16 | −0.4359 (8) | 0.2947 (7) | 0.3918 (7) | 0.0415 (15) | |
H16 | −0.5389 | 0.2874 | 0.4030 | 0.050* | |
C17 | −0.3210 (8) | 0.1850 (6) | 0.4111 (7) | 0.0413 (15) | |
H17 | −0.3447 | 0.1027 | 0.4339 | 0.050* | |
C18 | −0.1700 (8) | 0.2013 (6) | 0.3954 (7) | 0.0396 (14) | |
H18 | −0.0937 | 0.1290 | 0.4106 | 0.048* | |
Cl1 | 0.2047 (2) | 1.51507 (16) | 0.35012 (17) | 0.0436 (4) | |
Cl2 | 0.2358 (3) | 1.10739 (19) | 0.4104 (2) | 0.0581 (5) | |
Hg1 | 0.13517 (3) | 1.31748 (2) | 0.31567 (2) | 0.04162 (12) | |
N1 | 0.2955 (6) | 1.2612 (5) | 0.0831 (5) | 0.0361 (11) | |
N2 | −0.1291 (6) | 0.3179 (5) | 0.3590 (5) | 0.0328 (11) | |
O1 | 0.2274 (7) | 0.9563 (5) | 0.0059 (5) | 0.0490 (13) | |
O2 | −0.0724 (6) | 0.5467 (4) | 0.1880 (5) | 0.0450 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.046 (4) | 0.033 (3) | 0.047 (4) | −0.016 (3) | −0.007 (3) | −0.005 (3) |
C2 | 0.056 (4) | 0.044 (3) | 0.045 (4) | −0.027 (3) | −0.006 (3) | 0.006 (3) |
C3 | 0.048 (4) | 0.051 (4) | 0.042 (4) | −0.016 (3) | −0.007 (3) | 0.006 (3) |
C4 | 0.055 (4) | 0.041 (3) | 0.044 (4) | −0.023 (3) | −0.022 (3) | 0.005 (3) |
C5 | 0.039 (3) | 0.028 (3) | 0.043 (3) | −0.014 (2) | −0.022 (3) | 0.008 (2) |
C6 | 0.055 (4) | 0.035 (3) | 0.044 (3) | −0.025 (3) | −0.021 (3) | 0.005 (3) |
C7 | 0.052 (4) | 0.029 (3) | 0.035 (3) | −0.018 (3) | −0.019 (3) | 0.004 (2) |
C8 | 0.052 (4) | 0.029 (3) | 0.040 (3) | −0.011 (3) | 0.004 (3) | −0.015 (3) |
C9 | 0.049 (4) | 0.036 (3) | 0.041 (3) | −0.019 (3) | −0.006 (3) | −0.003 (3) |
C10 | 0.041 (3) | 0.026 (2) | 0.031 (3) | −0.009 (2) | −0.016 (2) | −0.005 (2) |
C11 | 0.059 (4) | 0.034 (3) | 0.029 (3) | −0.018 (3) | −0.012 (3) | −0.009 (2) |
C12 | 0.061 (4) | 0.049 (4) | 0.031 (3) | −0.028 (3) | −0.017 (3) | 0.005 (3) |
C13 | 0.043 (3) | 0.030 (3) | 0.039 (3) | −0.013 (3) | −0.014 (3) | 0.006 (2) |
C14 | 0.037 (3) | 0.030 (3) | 0.025 (3) | −0.006 (2) | −0.008 (2) | −0.002 (2) |
C15 | 0.034 (3) | 0.046 (3) | 0.047 (4) | −0.018 (3) | −0.020 (3) | 0.011 (3) |
C16 | 0.036 (3) | 0.044 (3) | 0.044 (3) | −0.017 (3) | −0.010 (3) | −0.004 (3) |
C17 | 0.041 (3) | 0.040 (3) | 0.044 (3) | −0.022 (3) | −0.011 (3) | 0.005 (3) |
C18 | 0.040 (3) | 0.029 (3) | 0.043 (3) | −0.008 (3) | −0.011 (3) | 0.003 (3) |
Cl1 | 0.0489 (8) | 0.0469 (8) | 0.0472 (9) | −0.0256 (7) | −0.0236 (7) | 0.0053 (7) |
Cl2 | 0.0738 (12) | 0.0447 (9) | 0.0561 (11) | −0.0065 (9) | −0.0337 (10) | 0.0111 (8) |
Hg1 | 0.04200 (17) | 0.04003 (17) | 0.05152 (19) | −0.01992 (12) | −0.02262 (13) | 0.00908 (12) |
N1 | 0.039 (3) | 0.028 (2) | 0.038 (3) | −0.011 (2) | −0.011 (2) | 0.002 (2) |
N2 | 0.035 (2) | 0.030 (2) | 0.035 (3) | −0.012 (2) | −0.014 (2) | 0.001 (2) |
O1 | 0.070 (3) | 0.042 (2) | 0.038 (2) | −0.034 (2) | −0.012 (2) | 0.001 (2) |
O2 | 0.063 (3) | 0.040 (2) | 0.038 (2) | −0.031 (2) | −0.015 (2) | 0.0025 (19) |
C1—N1 | 1.338 (8) | C10—C11 | 1.393 (8) |
C1—C2 | 1.367 (9) | C11—C12 | 1.374 (9) |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
C2—C3 | 1.369 (10) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—O2 | 1.410 (8) |
C3—C4 | 1.380 (9) | C13—C14 | 1.491 (8) |
C3—H3 | 0.9300 | C13—H13A | 0.9700 |
C4—C5 | 1.393 (9) | C13—H13B | 0.9700 |
C4—H4 | 0.9300 | C14—N2 | 1.349 (8) |
C5—N1 | 1.341 (8) | C14—C15 | 1.391 (9) |
C5—C6 | 1.502 (8) | C15—C16 | 1.375 (9) |
C6—O1 | 1.413 (7) | C15—H15 | 0.9300 |
C6—H6A | 0.9700 | C16—C17 | 1.389 (10) |
C6—H6B | 0.9700 | C16—H16 | 0.9300 |
C7—C8 | 1.380 (9) | C17—C18 | 1.387 (9) |
C7—C12 | 1.383 (9) | C17—H17 | 0.9300 |
C7—O1 | 1.386 (7) | C18—N2 | 1.349 (8) |
C8—C9 | 1.379 (9) | C18—H18 | 0.9300 |
C8—H8 | 0.9300 | Hg1—Cl1 | 2.3981 (18) |
C9—C10 | 1.378 (8) | Hg1—Cl2 | 2.452 (2) |
C9—H9 | 0.9300 | Hg1—N2i | 2.282 (5) |
C10—O2 | 1.385 (7) | Hg1—N1 | 2.411 (5) |
N1—C1—C2 | 123.4 (6) | C11—C12—H12 | 119.5 |
N1—C1—H1 | 118.3 | C7—C12—H12 | 119.5 |
C2—C1—H1 | 118.3 | O2—C13—C14 | 109.4 (5) |
C1—C2—C3 | 118.8 (6) | O2—C13—H13A | 109.8 |
C1—C2—H2 | 120.6 | C14—C13—H13A | 109.8 |
C3—C2—H2 | 120.6 | O2—C13—H13B | 109.8 |
C2—C3—C4 | 119.1 (6) | C14—C13—H13B | 109.8 |
C2—C3—H3 | 120.4 | H13A—C13—H13B | 108.3 |
C4—C3—H3 | 120.4 | N2—C14—C15 | 121.4 (6) |
C3—C4—C5 | 119.0 (6) | N2—C14—C13 | 116.8 (6) |
C3—C4—H4 | 120.5 | C15—C14—C13 | 121.6 (6) |
C5—C4—H4 | 120.5 | C16—C15—C14 | 119.7 (6) |
N1—C5—C4 | 121.6 (6) | C16—C15—H15 | 120.1 |
N1—C5—C6 | 116.1 (5) | C14—C15—H15 | 120.1 |
C4—C5—C6 | 122.3 (6) | C15—C16—C17 | 119.3 (6) |
O1—C6—C5 | 108.7 (5) | C15—C16—H16 | 120.3 |
O1—C6—H6A | 109.9 | C17—C16—H16 | 120.3 |
C5—C6—H6A | 109.9 | C18—C17—C16 | 118.2 (6) |
O1—C6—H6B | 109.9 | C18—C17—H17 | 120.9 |
C5—C6—H6B | 109.9 | C16—C17—H17 | 120.9 |
H6A—C6—H6B | 108.3 | N2—C18—C17 | 122.7 (6) |
C8—C7—C12 | 119.7 (6) | N2—C18—H18 | 118.6 |
C8—C7—O1 | 124.9 (5) | C17—C18—H18 | 118.6 |
C12—C7—O1 | 115.4 (6) | N2i—Hg1—Cl1 | 122.30 (12) |
C9—C8—C7 | 119.8 (5) | N2i—Hg1—N1 | 107.69 (19) |
C9—C8—H8 | 120.1 | Cl1—Hg1—N1 | 102.88 (13) |
C7—C8—H8 | 120.1 | N2i—Hg1—Cl2 | 102.39 (14) |
C10—C9—C8 | 120.6 (6) | Cl1—Hg1—Cl2 | 118.53 (8) |
C10—C9—H9 | 119.7 | N1—Hg1—Cl2 | 100.63 (13) |
C8—C9—H9 | 119.7 | C1—N1—C5 | 118.0 (5) |
C9—C10—O2 | 125.7 (5) | C1—N1—Hg1 | 114.8 (4) |
C9—C10—C11 | 119.9 (5) | C5—N1—Hg1 | 126.7 (4) |
O2—C10—C11 | 114.3 (5) | C14—N2—C18 | 118.6 (5) |
C12—C11—C10 | 119.1 (5) | C14—N2—Hg1ii | 123.9 (4) |
C12—C11—H11 | 120.4 | C18—N2—Hg1ii | 117.3 (4) |
C10—C11—H11 | 120.4 | C7—O1—C6 | 116.8 (5) |
C11—C12—C7 | 121.0 (6) | C10—O2—C13 | 116.3 (4) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1iii | 0.93 | 2.82 | 3.692 (8) | 157 |
C11—H11···O2iv | 0.93 | 2.51 | 3.338 (9) | 149 |
Symmetry codes: (iii) −x+1, −y+3, −z; (iv) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [HgCl2(C18H16N2O2)] |
Mr | 563.82 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.201 (5), 10.335 (5), 11.040 (6) |
α, β, γ (°) | 86.11 (2), 66.51 (2), 73.860 (18) |
V (Å3) | 923.8 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.63 |
Crystal size (mm) | 0.19 × 0.17 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.288, 0.325 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9080, 4179, 3688 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.122, 1.16 |
No. of reflections | 4179 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.56, −1.74 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1i | 0.93 | 2.82 | 3.692 (8) | 157 |
C11—H11···O2ii | 0.93 | 2.51 | 3.338 (9) | 149 |
Symmetry codes: (i) −x+1, −y+3, −z; (ii) −x, −y+1, −z. |
Acknowledgements
The authors thank the Project of the Educational Commission of Heilongjiang Province of China (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 can react with transition metals to construct helical-like structures. Recently, as a continuation of previous studies (Liu et al., 2010a, b), we report here the crystal structure of the title compound.
In the title compound, the HgII atom is four-coordinated by two Cl atoms and two N atoms from two 1,4-bis(pyridin-2-ylmethoxy)benzene ligands, forming a tetrahedral geometry (Fig. 1). The Hg—Cl bond lengths are 2.398 (2) and 2.452 (2) Å, and Hg—N bond lengths are 2.282 (5) and 2.411 (5) Å. The angles around the Hg atom are in a range of 100.63 (13)–122.30 (12)°. The ligand shows a noncoplanar conformation, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.275 (17) and 74.020 (14)°. In the crystal, the flexible ligands link the HgII atoms into a chain running along [0 1 0], with an Hg···Hg separation of 10.335 (5)Å, which is equal to the b axis of the unit cell (Fig. 2). The chains are connected by C—H···O and C—H···Cl hydrogen bonds (Table 1).