metal-organic compounds
Poly[[diaquabis{μ-4-[6-(4-carboxyphenyl)-4,4′-bipyridin-2-yl]benzoato-κ2O:N4′}zinc] dimethylformamide tetrasolvate]
aState Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China
*Correspondence e-mail: songsy@ciac.jl.cn
In the title compound, {[Zn(C24H15N2O4)2(H2O)2]·4C3H7NO}n, the ZnII ion is located on an inversion center and is six-coordinated by two N atoms from two ligands, two carboxylate O atoms from two other symmetry-related ligands and two O atoms from two water molecules, furnishing a slightly distorted octahedral geometry. The ZnII atoms are connected by the bridging ligands into a layer parallel to (101). O—H⋯O hydrogen bonds link the layers and the dimethylformamide solvent molecules. π–π interactions between the pyridine and benzene rings [centroid–centroid distances = 3.7428 (17) and 3.7619 (17) Å] and intralayer O—H⋯O hydrogen bonds are also present.
Related literature
For the design of transition metal complexes with supramolecular structures, see: Li et al. (2011); Wang et al. (2010); Yang et al. (2007). For related structures, see: Song et al. (2012).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536812043838/hy2597sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043838/hy2597Isup2.hkl
Zn(NO3)2.6H2O (0.008 g, 0.025 mmol) and bpydbH2 (0.010 g, 0.025 mmol) were suspended in a mixed solution of DMF (4 ml) and H2O (0.5 ml). The mixture was heated in a 15 ml Teflon-lined stainless-steel autoclave at 90°C for 3 days. After it was cooled to room temperature slowly, colorless crystals were collected by filtration, washed with DMF and dried in air, with a yield of 59% based on bpydbH2.
H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). H atoms bonded to O atoms were located in a difference Fourier map and refined with distance restraints of O—H = 0.85 (1) Å and with Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Zn(C24H15N2O4)2(H2O)2]·4C3H7NO | F(000) = 1240 |
Mr = 1184.57 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5607 reflections |
a = 7.4744 (5) Å | θ = 1.0–26.1° |
b = 17.7122 (13) Å | µ = 0.51 mm−1 |
c = 21.4993 (15) Å | T = 293 K |
β = 95.075 (1)° | Block, colorless |
V = 2835.1 (3) Å3 | 0.25 × 0.22 × 0.19 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 5606 independent reflections |
Radiation source: fine-focus sealed tube | 3804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ϕ and ω scans | θmax = 26.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→9 |
Tmin = 0.839, Tmax = 0.915 | k = −16→21 |
15534 measured reflections | l = −26→21 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.078P)2 + 1.0747P] where P = (Fo2 + 2Fc2)/3 |
5606 reflections | (Δ/σ)max < 0.001 |
385 parameters | Δρmax = 0.40 e Å−3 |
3 restraints | Δρmin = −0.35 e Å−3 |
[Zn(C24H15N2O4)2(H2O)2]·4C3H7NO | V = 2835.1 (3) Å3 |
Mr = 1184.57 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4744 (5) Å | µ = 0.51 mm−1 |
b = 17.7122 (13) Å | T = 293 K |
c = 21.4993 (15) Å | 0.25 × 0.22 × 0.19 mm |
β = 95.075 (1)° |
Bruker APEXII CCD diffractometer | 5606 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3804 reflections with I > 2σ(I) |
Tmin = 0.839, Tmax = 0.915 | Rint = 0.044 |
15534 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 3 restraints |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.40 e Å−3 |
5606 reflections | Δρmin = −0.35 e Å−3 |
385 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 | ||
Zn1 | 1.0000 | 0.5000 | 0.0000 | 0.03205 (18) | |
C1 | 0.6503 (5) | 0.73356 (19) | 0.63443 (16) | 0.0392 (8) | |
C2 | 0.6897 (4) | 0.66640 (18) | 0.59720 (14) | 0.0331 (7) | |
C3 | 0.6424 (4) | 0.59554 (18) | 0.61726 (15) | 0.0347 (8) | |
H3 | 0.5935 | 0.5901 | 0.6553 | 0.042* | |
C4 | 0.6676 (4) | 0.53241 (19) | 0.58068 (14) | 0.0318 (7) | |
H4 | 0.6355 | 0.4850 | 0.5945 | 0.038* | |
C5 | 0.7403 (4) | 0.53927 (17) | 0.52353 (13) | 0.0266 (6) | |
C6 | 0.7865 (4) | 0.61109 (18) | 0.50425 (15) | 0.0317 (7) | |
H6 | 0.8333 | 0.6170 | 0.4659 | 0.038* | |
C7 | 0.7642 (4) | 0.67359 (18) | 0.54074 (15) | 0.0336 (7) | |
H7 | 0.7993 | 0.7209 | 0.5275 | 0.040* | |
C8 | 0.7645 (4) | 0.47318 (18) | 0.48218 (14) | 0.0275 (7) | |
C9 | 0.7387 (4) | 0.39894 (17) | 0.50138 (14) | 0.0275 (7) | |
H9 | 0.7094 | 0.3891 | 0.5417 | 0.033* | |
C10 | 0.7572 (4) | 0.33962 (17) | 0.45977 (13) | 0.0264 (6) | |
C11 | 0.8034 (4) | 0.35839 (17) | 0.40001 (13) | 0.0288 (7) | |
H11 | 0.8162 | 0.3207 | 0.3706 | 0.035* | |
C12 | 0.8302 (4) | 0.43340 (17) | 0.38481 (13) | 0.0263 (6) | |
C13 | 0.8806 (4) | 0.45519 (17) | 0.32174 (13) | 0.0278 (7) | |
C14 | 0.8268 (4) | 0.41227 (18) | 0.26902 (14) | 0.0329 (7) | |
H14 | 0.7549 | 0.3700 | 0.2729 | 0.039* | |
C15 | 0.8791 (4) | 0.43189 (18) | 0.21099 (14) | 0.0326 (7) | |
H15 | 0.8420 | 0.4028 | 0.1762 | 0.039* | |
C16 | 0.9868 (4) | 0.49489 (17) | 0.20442 (14) | 0.0283 (7) | |
C17 | 1.0387 (4) | 0.53839 (18) | 0.25678 (14) | 0.0321 (7) | |
H17 | 1.1100 | 0.5809 | 0.2528 | 0.038* | |
C18 | 0.9856 (4) | 0.51921 (18) | 0.31450 (14) | 0.0324 (7) | |
H18 | 1.0202 | 0.5492 | 0.3490 | 0.039* | |
C19 | 1.0453 (5) | 0.51556 (17) | 0.14145 (15) | 0.0333 (8) | |
C20 | 0.7223 (4) | 0.26062 (17) | 0.47603 (13) | 0.0266 (6) | |
C21 | 0.7949 (4) | 0.19986 (18) | 0.44509 (14) | 0.0344 (8) | |
H21 | 0.8797 | 0.2085 | 0.4168 | 0.041* | |
C22 | 0.7410 (4) | 0.12758 (18) | 0.45651 (14) | 0.0348 (7) | |
H22 | 0.7923 | 0.0882 | 0.4357 | 0.042* | |
C23 | 0.5550 (4) | 0.16840 (18) | 0.52842 (14) | 0.0326 (7) | |
H23 | 0.4745 | 0.1578 | 0.5578 | 0.039* | |
C24 | 0.6034 (4) | 0.24235 (17) | 0.52010 (13) | 0.0292 (7) | |
H24 | 0.5568 | 0.2802 | 0.5439 | 0.035* | |
C25 | 0.5183 (11) | 0.7258 (3) | 0.2575 (3) | 0.128 (3) | |
H25A | 0.5527 | 0.7407 | 0.2173 | 0.192* | |
H25B | 0.5922 | 0.7515 | 0.2896 | 0.192* | |
H25C | 0.3947 | 0.7387 | 0.2606 | 0.192* | |
C26 | 0.5986 (7) | 0.6048 (3) | 0.2118 (2) | 0.0877 (17) | |
H26A | 0.6200 | 0.6397 | 0.1791 | 0.132* | |
H26B | 0.5067 | 0.5697 | 0.1970 | 0.132* | |
H26C | 0.7073 | 0.5778 | 0.2243 | 0.132* | |
C27 | 0.5016 (7) | 0.6134 (3) | 0.3160 (2) | 0.0726 (13) | |
H27 | 0.5261 | 0.5620 | 0.3197 | 0.087* | |
C28 | 0.8396 (6) | 0.1388 (3) | 0.6757 (2) | 0.0836 (16) | |
H28A | 0.8060 | 0.1752 | 0.7056 | 0.125* | |
H28B | 0.8962 | 0.0964 | 0.6971 | 0.125* | |
H28C | 0.7344 | 0.1222 | 0.6506 | 0.125* | |
C29 | 1.0019 (7) | 0.2524 (3) | 0.6437 (2) | 0.0759 (14) | |
H29A | 0.9434 | 0.2711 | 0.6786 | 0.114* | |
H29B | 0.9580 | 0.2792 | 0.6066 | 0.114* | |
H29C | 1.1291 | 0.2599 | 0.6513 | 0.114* | |
C30 | 1.0301 (5) | 0.1338 (2) | 0.59015 (18) | 0.0506 (10) | |
H30 | 0.9951 | 0.0835 | 0.5854 | 0.061* | |
N1 | 0.8119 (3) | 0.49033 (14) | 0.42511 (11) | 0.0278 (6) | |
N2 | 0.6181 (3) | 0.11067 (14) | 0.49621 (11) | 0.0313 (6) | |
N3 | 0.5410 (4) | 0.64597 (18) | 0.26498 (14) | 0.0501 (8) | |
N4 | 0.9645 (4) | 0.1733 (2) | 0.63570 (15) | 0.0520 (8) | |
O1 | 0.9686 (3) | 0.48245 (12) | 0.09483 (9) | 0.0361 (6) | |
O2 | 1.1689 (3) | 0.56380 (13) | 0.13980 (10) | 0.0432 (6) | |
O3 | 0.7257 (4) | 0.79565 (15) | 0.61423 (13) | 0.0569 (7) | |
H3A | 0.683 (6) | 0.8386 (13) | 0.624 (2) | 0.085* | |
O4 | 0.5576 (4) | 0.73346 (15) | 0.67822 (12) | 0.0544 (7) | |
O5 | 0.4357 (5) | 0.64314 (19) | 0.35968 (14) | 0.0839 (11) | |
O6 | 1.1334 (4) | 0.15890 (17) | 0.55402 (13) | 0.0590 (8) | |
O1W | 1.2630 (3) | 0.54461 (14) | 0.02156 (11) | 0.0416 (6) | |
H1A | 1.299 (5) | 0.5844 (14) | 0.0047 (18) | 0.062* | |
H1B | 1.278 (5) | 0.559 (2) | 0.0592 (8) | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0519 (3) | 0.0240 (3) | 0.0219 (3) | 0.0006 (2) | 0.0128 (2) | 0.0000 (2) |
C1 | 0.050 (2) | 0.033 (2) | 0.0353 (19) | 0.0030 (16) | 0.0075 (16) | −0.0027 (15) |
C2 | 0.0362 (17) | 0.0336 (18) | 0.0293 (17) | 0.0046 (14) | 0.0013 (14) | −0.0048 (14) |
C3 | 0.0421 (18) | 0.0354 (19) | 0.0278 (17) | 0.0034 (15) | 0.0100 (14) | 0.0005 (14) |
C4 | 0.0413 (18) | 0.0293 (17) | 0.0254 (16) | 0.0013 (14) | 0.0066 (14) | 0.0021 (13) |
C5 | 0.0270 (15) | 0.0278 (17) | 0.0248 (16) | 0.0007 (13) | 0.0013 (12) | 0.0009 (12) |
C6 | 0.0361 (17) | 0.0308 (18) | 0.0291 (17) | −0.0009 (14) | 0.0081 (14) | −0.0001 (13) |
C7 | 0.0378 (18) | 0.0275 (17) | 0.0360 (18) | −0.0006 (14) | 0.0060 (15) | 0.0006 (14) |
C8 | 0.0272 (15) | 0.0292 (16) | 0.0266 (16) | −0.0020 (13) | 0.0054 (13) | −0.0014 (13) |
C9 | 0.0295 (16) | 0.0309 (17) | 0.0228 (15) | −0.0004 (13) | 0.0057 (13) | 0.0016 (12) |
C10 | 0.0298 (15) | 0.0284 (16) | 0.0214 (15) | 0.0015 (13) | 0.0046 (12) | 0.0016 (12) |
C11 | 0.0371 (17) | 0.0282 (17) | 0.0217 (15) | 0.0012 (13) | 0.0063 (13) | −0.0005 (12) |
C12 | 0.0317 (16) | 0.0287 (17) | 0.0187 (14) | −0.0002 (13) | 0.0039 (12) | 0.0017 (12) |
C13 | 0.0338 (16) | 0.0274 (17) | 0.0229 (15) | 0.0020 (13) | 0.0074 (13) | 0.0034 (12) |
C14 | 0.0452 (19) | 0.0290 (17) | 0.0261 (16) | −0.0059 (14) | 0.0118 (14) | 0.0008 (13) |
C15 | 0.0480 (19) | 0.0296 (18) | 0.0211 (15) | 0.0010 (14) | 0.0075 (14) | 0.0008 (13) |
C16 | 0.0390 (17) | 0.0244 (16) | 0.0226 (15) | 0.0038 (13) | 0.0102 (13) | 0.0026 (12) |
C17 | 0.0437 (18) | 0.0272 (17) | 0.0263 (16) | −0.0049 (14) | 0.0081 (14) | 0.0032 (13) |
C18 | 0.0448 (18) | 0.0322 (18) | 0.0209 (16) | −0.0038 (14) | 0.0065 (14) | −0.0012 (12) |
C19 | 0.0482 (19) | 0.0265 (18) | 0.0268 (17) | 0.0052 (15) | 0.0115 (15) | 0.0043 (13) |
C20 | 0.0333 (16) | 0.0241 (16) | 0.0229 (15) | 0.0006 (13) | 0.0054 (12) | 0.0001 (12) |
C21 | 0.0439 (19) | 0.0327 (18) | 0.0286 (17) | −0.0002 (15) | 0.0144 (15) | 0.0001 (13) |
C22 | 0.0481 (19) | 0.0285 (17) | 0.0296 (17) | 0.0029 (15) | 0.0132 (15) | −0.0025 (13) |
C23 | 0.0461 (19) | 0.0294 (17) | 0.0240 (16) | 0.0000 (14) | 0.0124 (14) | 0.0014 (13) |
C24 | 0.0406 (17) | 0.0264 (16) | 0.0213 (15) | −0.0009 (13) | 0.0063 (13) | −0.0003 (12) |
C25 | 0.226 (8) | 0.052 (4) | 0.107 (5) | 0.005 (4) | 0.016 (5) | 0.023 (3) |
C26 | 0.084 (3) | 0.127 (5) | 0.055 (3) | 0.038 (3) | 0.025 (3) | 0.002 (3) |
C27 | 0.103 (4) | 0.055 (3) | 0.064 (3) | 0.011 (3) | 0.032 (3) | 0.009 (2) |
C28 | 0.078 (3) | 0.116 (5) | 0.061 (3) | −0.027 (3) | 0.031 (3) | −0.016 (3) |
C29 | 0.092 (3) | 0.065 (3) | 0.073 (3) | 0.005 (3) | 0.020 (3) | −0.018 (2) |
C30 | 0.054 (2) | 0.051 (2) | 0.047 (2) | 0.0043 (19) | 0.0038 (19) | −0.0033 (18) |
N1 | 0.0320 (13) | 0.0289 (15) | 0.0235 (13) | −0.0014 (11) | 0.0069 (11) | 0.0025 (10) |
N2 | 0.0468 (16) | 0.0251 (14) | 0.0232 (13) | −0.0013 (12) | 0.0103 (12) | 0.0005 (10) |
N3 | 0.059 (2) | 0.051 (2) | 0.0425 (18) | 0.0119 (16) | 0.0188 (15) | 0.0105 (15) |
N4 | 0.0484 (18) | 0.063 (2) | 0.0460 (19) | 0.0022 (16) | 0.0137 (15) | −0.0078 (16) |
O1 | 0.0617 (15) | 0.0290 (13) | 0.0190 (11) | −0.0026 (10) | 0.0118 (11) | −0.0013 (9) |
O2 | 0.0644 (16) | 0.0364 (14) | 0.0311 (12) | −0.0112 (12) | 0.0170 (11) | 0.0010 (10) |
O3 | 0.0751 (19) | 0.0377 (16) | 0.0612 (17) | 0.0008 (14) | 0.0256 (15) | −0.0095 (13) |
O4 | 0.0735 (18) | 0.0479 (17) | 0.0439 (15) | 0.0008 (14) | 0.0177 (14) | −0.0080 (12) |
O5 | 0.134 (3) | 0.071 (2) | 0.0527 (18) | 0.008 (2) | 0.044 (2) | −0.0085 (16) |
O6 | 0.0602 (17) | 0.065 (2) | 0.0548 (17) | 0.0113 (14) | 0.0242 (14) | −0.0028 (14) |
O1W | 0.0544 (15) | 0.0381 (15) | 0.0345 (13) | −0.0061 (12) | 0.0165 (12) | −0.0018 (11) |
Zn1—O1 | 2.096 (2) | C18—H18 | 0.9300 |
Zn1—O1i | 2.096 (2) | C19—O1 | 1.255 (4) |
Zn1—O1W | 2.131 (3) | C19—O2 | 1.261 (4) |
Zn1—O1Wi | 2.131 (3) | C20—C24 | 1.393 (4) |
Zn1—N2ii | 2.154 (3) | C20—C21 | 1.400 (4) |
Zn1—N2iii | 2.154 (3) | C21—C22 | 1.371 (4) |
C1—O4 | 1.217 (4) | C21—H21 | 0.9300 |
C1—O3 | 1.326 (4) | C22—N2 | 1.342 (4) |
C1—C2 | 1.478 (4) | C22—H22 | 0.9300 |
C2—C3 | 1.383 (5) | C23—N2 | 1.344 (4) |
C2—C7 | 1.385 (4) | C23—C24 | 1.375 (4) |
C3—C4 | 1.389 (4) | C23—H23 | 0.9300 |
C3—H3 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.392 (4) | C25—N3 | 1.431 (6) |
C4—H4 | 0.9300 | C25—H25A | 0.9600 |
C5—C6 | 1.391 (4) | C25—H25B | 0.9600 |
C5—C8 | 1.490 (4) | C25—H25C | 0.9600 |
C6—C7 | 1.375 (4) | C26—N3 | 1.453 (5) |
C6—H6 | 0.9300 | C26—H26A | 0.9600 |
C7—H7 | 0.9300 | C26—H26B | 0.9600 |
C8—N1 | 1.342 (4) | C26—H26C | 0.9600 |
C8—C9 | 1.397 (4) | C27—O5 | 1.217 (5) |
C9—C10 | 1.395 (4) | C27—N3 | 1.297 (5) |
C9—H9 | 0.9300 | C27—H27 | 0.9300 |
C10—C11 | 1.400 (4) | C28—N4 | 1.458 (5) |
C10—C20 | 1.471 (4) | C28—H28A | 0.9600 |
C11—C12 | 1.387 (4) | C28—H28B | 0.9600 |
C11—H11 | 0.9300 | C28—H28C | 0.9600 |
C12—N1 | 1.344 (4) | C29—N4 | 1.436 (5) |
C12—C13 | 1.490 (4) | C29—H29A | 0.9600 |
C13—C14 | 1.394 (4) | C29—H29B | 0.9600 |
C13—C18 | 1.396 (4) | C29—H29C | 0.9600 |
C14—C15 | 1.384 (4) | C30—O6 | 1.226 (4) |
C14—H14 | 0.9300 | C30—N4 | 1.333 (5) |
C15—C16 | 1.390 (4) | C30—H30 | 0.9300 |
C15—H15 | 0.9300 | N2—Zn1iv | 2.154 (3) |
C16—C17 | 1.391 (4) | O3—H3A | 0.86 (1) |
C16—C19 | 1.504 (4) | O1W—H1A | 0.85 (1) |
C17—C18 | 1.378 (4) | O1W—H1B | 0.85 (1) |
C17—H17 | 0.9300 | ||
O1—Zn1—O1i | 180.0 | C17—C18—C13 | 120.7 (3) |
O1—Zn1—O1W | 91.38 (9) | C17—C18—H18 | 119.7 |
O1i—Zn1—O1W | 88.62 (9) | C13—C18—H18 | 119.7 |
O1—Zn1—O1Wi | 88.62 (9) | O1—C19—O2 | 125.3 (3) |
O1i—Zn1—O1Wi | 91.38 (9) | O1—C19—C16 | 117.1 (3) |
O1W—Zn1—O1Wi | 180.0 | O2—C19—C16 | 117.5 (3) |
O1—Zn1—N2ii | 89.05 (9) | C24—C20—C21 | 116.2 (3) |
O1i—Zn1—N2ii | 90.95 (9) | C24—C20—C10 | 121.3 (3) |
O1W—Zn1—N2ii | 88.43 (10) | C21—C20—C10 | 122.3 (3) |
O1Wi—Zn1—N2ii | 91.57 (10) | C22—C21—C20 | 120.1 (3) |
O1—Zn1—N2iii | 90.95 (9) | C22—C21—H21 | 120.0 |
O1i—Zn1—N2iii | 89.05 (9) | C20—C21—H21 | 120.0 |
O1W—Zn1—N2iii | 91.57 (10) | N2—C22—C21 | 123.4 (3) |
O1Wi—Zn1—N2iii | 88.43 (10) | N2—C22—H22 | 118.3 |
N2ii—Zn1—N2iii | 180.0 | C21—C22—H22 | 118.3 |
O4—C1—O3 | 122.8 (3) | N2—C23—C24 | 123.3 (3) |
O4—C1—C2 | 124.9 (3) | N2—C23—H23 | 118.3 |
O3—C1—C2 | 112.3 (3) | C24—C23—H23 | 118.3 |
C3—C2—C7 | 119.4 (3) | C23—C24—C20 | 120.1 (3) |
C3—C2—C1 | 119.5 (3) | C23—C24—H24 | 120.0 |
C7—C2—C1 | 121.0 (3) | C20—C24—H24 | 120.0 |
C2—C3—C4 | 120.2 (3) | N3—C25—H25A | 109.5 |
C2—C3—H3 | 119.9 | N3—C25—H25B | 109.5 |
C4—C3—H3 | 119.9 | H25A—C25—H25B | 109.5 |
C3—C4—C5 | 120.8 (3) | N3—C25—H25C | 109.5 |
C3—C4—H4 | 119.6 | H25A—C25—H25C | 109.5 |
C5—C4—H4 | 119.6 | H25B—C25—H25C | 109.5 |
C6—C5—C4 | 118.0 (3) | N3—C26—H26A | 109.5 |
C6—C5—C8 | 119.6 (3) | N3—C26—H26B | 109.5 |
C4—C5—C8 | 122.4 (3) | H26A—C26—H26B | 109.5 |
C7—C6—C5 | 121.4 (3) | N3—C26—H26C | 109.5 |
C7—C6—H6 | 119.3 | H26A—C26—H26C | 109.5 |
C5—C6—H6 | 119.3 | H26B—C26—H26C | 109.5 |
C6—C7—C2 | 120.3 (3) | O5—C27—N3 | 126.7 (5) |
C6—C7—H7 | 119.9 | O5—C27—H27 | 116.6 |
C2—C7—H7 | 119.9 | N3—C27—H27 | 116.6 |
N1—C8—C9 | 122.5 (3) | N4—C28—H28A | 109.5 |
N1—C8—C5 | 115.0 (3) | N4—C28—H28B | 109.5 |
C9—C8—C5 | 122.4 (3) | H28A—C28—H28B | 109.5 |
C10—C9—C8 | 119.7 (3) | N4—C28—H28C | 109.5 |
C10—C9—H9 | 120.1 | H28A—C28—H28C | 109.5 |
C8—C9—H9 | 120.1 | H28B—C28—H28C | 109.5 |
C9—C10—C11 | 117.1 (3) | N4—C29—H29A | 109.5 |
C9—C10—C20 | 122.3 (3) | N4—C29—H29B | 109.5 |
C11—C10—C20 | 120.5 (3) | H29A—C29—H29B | 109.5 |
C12—C11—C10 | 119.8 (3) | N4—C29—H29C | 109.5 |
C12—C11—H11 | 120.1 | H29A—C29—H29C | 109.5 |
C10—C11—H11 | 120.1 | H29B—C29—H29C | 109.5 |
N1—C12—C11 | 122.8 (3) | O6—C30—N4 | 124.6 (4) |
N1—C12—C13 | 116.1 (3) | O6—C30—H30 | 117.7 |
C11—C12—C13 | 121.1 (3) | N4—C30—H30 | 117.7 |
C14—C13—C18 | 118.5 (3) | C8—N1—C12 | 118.0 (3) |
C14—C13—C12 | 121.4 (3) | C22—N2—C23 | 116.7 (3) |
C18—C13—C12 | 120.1 (3) | C22—N2—Zn1iv | 122.2 (2) |
C15—C14—C13 | 120.8 (3) | C23—N2—Zn1iv | 120.6 (2) |
C15—C14—H14 | 119.6 | C27—N3—C25 | 120.0 (4) |
C13—C14—H14 | 119.6 | C27—N3—C26 | 123.2 (4) |
C14—C15—C16 | 120.3 (3) | C25—N3—C26 | 116.6 (4) |
C14—C15—H15 | 119.8 | C30—N4—C29 | 121.4 (4) |
C16—C15—H15 | 119.8 | C30—N4—C28 | 120.6 (4) |
C15—C16—C17 | 119.0 (3) | C29—N4—C28 | 117.8 (4) |
C15—C16—C19 | 120.3 (3) | C19—O1—Zn1 | 128.7 (2) |
C17—C16—C19 | 120.7 (3) | C1—O3—H3A | 119 (3) |
C18—C17—C16 | 120.7 (3) | Zn1—O1W—H1A | 122 (3) |
C18—C17—H17 | 119.7 | Zn1—O1W—H1B | 111 (3) |
C16—C17—H17 | 119.7 | H1A—O1W—H1B | 98 (4) |
O4—C1—C2—C3 | −9.9 (5) | C19—C16—C17—C18 | −179.7 (3) |
O3—C1—C2—C3 | 171.1 (3) | C16—C17—C18—C13 | 0.8 (5) |
O4—C1—C2—C7 | 166.5 (3) | C14—C13—C18—C17 | −1.7 (5) |
O3—C1—C2—C7 | −12.6 (5) | C12—C13—C18—C17 | 177.6 (3) |
C7—C2—C3—C4 | −0.7 (5) | C15—C16—C19—O1 | 12.2 (4) |
C1—C2—C3—C4 | 175.7 (3) | C17—C16—C19—O1 | −167.6 (3) |
C2—C3—C4—C5 | −0.1 (5) | C15—C16—C19—O2 | −166.8 (3) |
C3—C4—C5—C6 | −0.1 (5) | C17—C16—C19—O2 | 13.4 (5) |
C3—C4—C5—C8 | −178.2 (3) | C9—C10—C20—C24 | 26.9 (4) |
C4—C5—C6—C7 | 1.1 (4) | C11—C10—C20—C24 | −150.4 (3) |
C8—C5—C6—C7 | 179.3 (3) | C9—C10—C20—C21 | −158.1 (3) |
C5—C6—C7—C2 | −1.9 (5) | C11—C10—C20—C21 | 24.6 (4) |
C3—C2—C7—C6 | 1.7 (5) | C24—C20—C21—C22 | 3.3 (4) |
C1—C2—C7—C6 | −174.6 (3) | C10—C20—C21—C22 | −171.9 (3) |
C6—C5—C8—N1 | −7.2 (4) | C20—C21—C22—N2 | 0.7 (5) |
C4—C5—C8—N1 | 170.9 (3) | N2—C23—C24—C20 | 0.6 (5) |
C6—C5—C8—C9 | 173.1 (3) | C21—C20—C24—C23 | −3.9 (4) |
C4—C5—C8—C9 | −8.8 (4) | C10—C20—C24—C23 | 171.3 (3) |
N1—C8—C9—C10 | −1.9 (4) | C9—C8—N1—C12 | 1.8 (4) |
C5—C8—C9—C10 | 177.7 (3) | C5—C8—N1—C12 | −177.9 (2) |
C8—C9—C10—C11 | 0.7 (4) | C11—C12—N1—C8 | −0.4 (4) |
C8—C9—C10—C20 | −176.6 (3) | C13—C12—N1—C8 | 179.2 (2) |
C9—C10—C11—C12 | 0.5 (4) | C21—C22—N2—C23 | −4.0 (5) |
C20—C10—C11—C12 | 177.9 (3) | C21—C22—N2—Zn1iv | 168.0 (2) |
C10—C11—C12—N1 | −0.7 (5) | C24—C23—N2—C22 | 3.4 (5) |
C10—C11—C12—C13 | 179.6 (3) | C24—C23—N2—Zn1iv | −168.8 (2) |
N1—C12—C13—C14 | −150.2 (3) | O5—C27—N3—C25 | 4.1 (8) |
C11—C12—C13—C14 | 29.5 (4) | O5—C27—N3—C26 | −172.1 (5) |
N1—C12—C13—C18 | 30.6 (4) | O6—C30—N4—C29 | 4.2 (6) |
C11—C12—C13—C18 | −149.7 (3) | O6—C30—N4—C28 | 178.8 (4) |
C18—C13—C14—C15 | 1.2 (5) | O2—C19—O1—Zn1 | −5.2 (5) |
C12—C13—C14—C15 | −178.1 (3) | C16—C19—O1—Zn1 | 175.85 (19) |
C13—C14—C15—C16 | 0.1 (5) | O1W—Zn1—O1—C19 | 24.7 (3) |
C14—C15—C16—C17 | −1.0 (5) | O1Wi—Zn1—O1—C19 | −155.3 (3) |
C14—C15—C16—C19 | 179.3 (3) | N2ii—Zn1—O1—C19 | 113.1 (3) |
C15—C16—C17—C18 | 0.5 (5) | N2iii—Zn1—O1—C19 | −66.9 (3) |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O6v | 0.85 (1) | 1.93 (2) | 2.750 (4) | 164 (4) |
O1W—H1B···O2 | 0.85 (1) | 1.98 (2) | 2.718 (3) | 145 (4) |
O3—H3A···O2vi | 0.86 (1) | 1.77 (2) | 2.592 (3) | 161 (5) |
Symmetry codes: (v) −x+5/2, y+1/2, −z+1/2; (vi) x−1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C24H15N2O4)2(H2O)2]·4C3H7NO |
Mr | 1184.57 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.4744 (5), 17.7122 (13), 21.4993 (15) |
β (°) | 95.075 (1) |
V (Å3) | 2835.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.25 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.839, 0.915 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15534, 5606, 3804 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.158, 1.05 |
No. of reflections | 5606 |
No. of parameters | 385 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.35 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O6i | 0.85 (1) | 1.93 (2) | 2.750 (4) | 164 (4) |
O1W—H1B···O2 | 0.85 (1) | 1.98 (2) | 2.718 (3) | 145 (4) |
O3—H3A···O2ii | 0.86 (1) | 1.77 (2) | 2.592 (3) | 161 (5) |
Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2. |
Acknowledgements
The authors are grateful for financial aid from the National Natural Science Foundation of China (grant No. 21001101).
References
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H.-J., Gao, Z.-Q. & Gu, J.-Z. (2011). Acta Cryst. E67, m919. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, S.-Y., Song, X.-Z., Zhao, S.-N., Qin, C., Su, S.-Q., Zhu, M., Hao, Z.-M. & Zhang, H.-J. (2012). Dalton Trans. 41, 10412–10421. Web of Science CSD CrossRef CAS PubMed Google Scholar
Wang, G.-H., Lei, Y.-Q., Wang, N., He, R.-L., Jia, H.-Q., Hu, N.-H. & Xu, J.-W. (2010). Cryst. Growth Des. 10, 534–540. Web of Science CrossRef CAS Google Scholar
Yang, X.-P., Jones, R. A., Rivers, J. H. & Lai, R. P. (2007). Dalton Trans. pp. 3936–3942. Web of Science CSD CrossRef Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The coordination chemistry of transition metal complexes is a rapidly growing area due to the ability of the resulting complexes to find applications in materials science with luminescent, magnetic, catalytic, and gas absorption and separation properties (Li et al., 2011; Yang et al., 2007). Multifunctional ligands can link metal ions into one-, two- or three-dimensional structures (Wang et al., 2010). In order to extend the investigations in this field, we used a multifunctional ligand, 4,4'-(4,4'-bipyridine-2,6-diyl)dibenzoic acid (bpydbH2), to design and synthesize the title zinc(II) complex and its structure is reported here.
The asymmetric unit of the title complex contains a half ZnII ion, one (bpydbH)- ligand, one aqua ligand and two lattice dimethylformamide (DMF) molecules. As shown in Fig. 1, the ZnII ion, lying on an inversion center, is six-coordinated by two N atoms from two (bpydbH)- ligands, two deprotonated carboxylate O atoms from the other two (bpydbH)- ligands and two aqua ligands, furnishing a slightly distorted octahedral geometry. The bond distances and angles are in the normal range (Song et al., 2012). The Zn nodes are extended by the (bpydbH)- linkers in four directions, forming a layer parallel to (101) (Fig. 2). Intralayer O—H···O hydrogen bonds stabilize the layer. O—H···O hydrogen bonds link the layers and the dimethylformamide solvent molecules. π–π interactions between the pyridine and benzene rings [centroid–centroid distances = 3.7428 (17) and 3.7619 (17) Å] are also present.