metal-organic compounds
catena-Poly[[diaqua(2,2′-bipyridine-κ2N,N′)zinc]-μ-2,2′-[1,4-phenylenebis(sulfanediyl)]diacetato-κ2O:O′]
aJinhua Professional Technical College, No. 1188 Wuzhou Street, Jinhua, Zhejiang 321007, People's Republic of China, and bZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: jh_ll@126.com
In the polymeric title complex, [Zn(C10H8O4S2)(C10H8N2)(H2O)2]n, the Zn2+ ion lies on a twofold rotation axis and exhibits an octahedral environment, in which it is coordinated by two trans O atoms from two symmetry-related 2,2′-[1,4-phenylenebis(sulfanediyl)]diacetate anions, two N atoms from one 2,2′-bipyridine ligand, and two cis O atoms from water molecules. The dihedral angle between the two pyridine rings is 11.5 (1)°. Adjacent Zn2+ ions are bridged in a monodentate manner by the diacetate anions, forming a chain structure extending parallel to [101], and are further linked into the final three-dimensional structure by O—H⋯O hydrogen bonds between the coordinating water molecules as donor and the non-coordinating carboxylate O atoms as acceptor atoms.
Related literature
For background to 1,4-benzenebis(thioacetic acid), including its synthesis and coordination behaviour, see: Yin & Feng (2009); Yin et al. (2009); Chen et al. (2010); Wang et al. (2011a,b); Jiang et al. (2012).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536811055310/wm2568sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811055310/wm2568Isup2.hkl
A mixture of 1,4-benzenebis(thioacetic acid) (0.103 g, 0.4 mmol), ZnCl2.6H2O (0.054 g, 0.4 mmol), 2,2'-bipy (0.031 g, 0.2 mmol), and Na2CO3 (0.042 g, 0.4 mmol) in H2O (16 ml)/C2H5OH (2 ml) was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 433 K for 72 h, then cooled to room temperature over 3 d. Colourless crystals suitable for X-ray analysis were obtained.
The carbon-bound H-atoms were positioned geometrically and included in the
using a riding model [aromatic C—H 0.93Å and aliphatic C—H 0.97 Å, Uiso(H) = 1.2Ueq(C)]. The oxygen-bound H-atoms were located in difference Fourier maps and refined with an O—H distance restrained to 0.85 Å and Uiso(H) = 1.2Ueq(O).Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).[Zn(C10H8O4S2)(C10H8N2)(H2O)2] | F(000) = 1056 |
Mr = 513.87 | Dx = 1.626 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7952 reflections |
a = 20.4396 (8) Å | θ = 1.9–27.7° |
b = 12.8695 (8) Å | µ = 1.41 mm−1 |
c = 7.9798 (4) Å | T = 296 K |
β = 90.765 (3)° | Block, colourless |
V = 2098.88 (19) Å3 | 0.22 × 0.16 × 0.11 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2448 independent reflections |
Radiation source: fine-focus sealed tube | 2237 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.7°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→26 |
Tmin = 0.761, Tmax = 0.853 | k = −15→16 |
16253 measured reflections | l = −10→10 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.043P)2 + 0.7442P] where P = (Fo2 + 2Fc2)/3 |
2448 reflections | (Δ/σ)max = 0.001 |
147 parameters | Δρmax = 0.31 e Å−3 |
3 restraints | Δρmin = −0.31 e Å−3 |
[Zn(C10H8O4S2)(C10H8N2)(H2O)2] | V = 2098.88 (19) Å3 |
Mr = 513.87 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.4396 (8) Å | µ = 1.41 mm−1 |
b = 12.8695 (8) Å | T = 296 K |
c = 7.9798 (4) Å | 0.22 × 0.16 × 0.11 mm |
β = 90.765 (3)° |
Bruker APEXII CCD diffractometer | 2448 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2237 reflections with I > 2σ(I) |
Tmin = 0.761, Tmax = 0.853 | Rint = 0.026 |
16253 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 3 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.31 e Å−3 |
2448 reflections | Δρmin = −0.31 e Å−3 |
147 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 | 0.5000 | 0.725191 (16) | 0.2500 | 0.03569 (9) | |
S1 | 0.676748 (19) | 0.62114 (4) | 0.78141 (5) | 0.04863 (12) | |
N1 | 0.44065 (7) | 0.85617 (9) | 0.31662 (16) | 0.0391 (3) | |
O1W | 0.57320 (6) | 0.61941 (8) | 0.18683 (14) | 0.0435 (3) | |
H1WA | 0.5703 (10) | 0.5693 (13) | 0.123 (2) | 0.052* | |
H1WB | 0.5785 (10) | 0.5933 (15) | 0.2793 (18) | 0.052* | |
O1 | 0.54190 (6) | 0.72445 (7) | 0.49896 (13) | 0.0398 (2) | |
O2 | 0.57240 (6) | 0.55857 (8) | 0.50514 (13) | 0.0446 (3) | |
C1 | 0.38250 (9) | 0.85086 (14) | 0.3913 (2) | 0.0484 (4) | |
H1A | 0.3633 | 0.7861 | 0.4061 | 0.058* | |
C2 | 0.34980 (10) | 0.93842 (17) | 0.4477 (2) | 0.0597 (5) | |
H2A | 0.3089 | 0.9329 | 0.4966 | 0.072* | |
C3 | 0.37950 (11) | 1.03389 (15) | 0.4292 (3) | 0.0618 (5) | |
H3A | 0.3594 | 1.0937 | 0.4688 | 0.074* | |
C4 | 0.43876 (10) | 1.03996 (13) | 0.3523 (2) | 0.0532 (4) | |
H4A | 0.4592 | 1.1040 | 0.3391 | 0.064* | |
C5 | 0.46836 (8) | 0.94978 (11) | 0.29374 (19) | 0.0403 (3) | |
C6 | 0.56711 (6) | 0.64669 (10) | 0.56961 (17) | 0.0319 (3) | |
C7 | 0.59312 (7) | 0.66315 (13) | 0.74760 (18) | 0.0395 (3) | |
H7A | 0.5652 | 0.6258 | 0.8245 | 0.047* | |
H7B | 0.5901 | 0.7365 | 0.7746 | 0.047* | |
C8 | 0.71752 (7) | 0.69346 (13) | 0.6228 (2) | 0.0408 (3) | |
C9 | 0.71738 (8) | 0.65950 (13) | 0.4586 (2) | 0.0479 (4) | |
H9A | 0.6958 | 0.5983 | 0.4300 | 0.057* | |
C10 | 0.75080 (8) | 0.78402 (14) | 0.6640 (2) | 0.0475 (4) | |
H10A | 0.7518 | 0.8070 | 0.7745 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.04999 (16) | 0.02228 (13) | 0.03467 (14) | 0.000 | −0.00485 (10) | 0.000 |
S1 | 0.0406 (2) | 0.0562 (3) | 0.0490 (2) | 0.00141 (17) | −0.00659 (17) | 0.01881 (18) |
N1 | 0.0518 (7) | 0.0284 (6) | 0.0367 (6) | 0.0019 (5) | −0.0129 (5) | −0.0020 (5) |
O1W | 0.0664 (7) | 0.0291 (5) | 0.0349 (5) | 0.0064 (5) | −0.0039 (5) | −0.0045 (4) |
O1 | 0.0540 (6) | 0.0316 (5) | 0.0336 (5) | 0.0051 (4) | −0.0085 (5) | −0.0008 (4) |
O2 | 0.0661 (7) | 0.0290 (5) | 0.0385 (5) | 0.0007 (5) | −0.0048 (5) | 0.0043 (4) |
C1 | 0.0531 (9) | 0.0449 (9) | 0.0468 (9) | 0.0033 (7) | −0.0084 (7) | −0.0017 (7) |
C2 | 0.0590 (11) | 0.0643 (12) | 0.0555 (11) | 0.0169 (9) | −0.0085 (8) | −0.0076 (9) |
C3 | 0.0744 (13) | 0.0478 (10) | 0.0626 (11) | 0.0254 (9) | −0.0234 (9) | −0.0171 (8) |
C4 | 0.0680 (11) | 0.0309 (8) | 0.0600 (10) | 0.0107 (7) | −0.0274 (9) | −0.0082 (7) |
C5 | 0.0546 (8) | 0.0258 (6) | 0.0398 (7) | 0.0028 (6) | −0.0231 (6) | −0.0023 (5) |
C6 | 0.0324 (6) | 0.0328 (7) | 0.0304 (6) | −0.0034 (5) | 0.0012 (5) | 0.0042 (5) |
C7 | 0.0400 (7) | 0.0479 (8) | 0.0307 (7) | 0.0045 (6) | −0.0003 (6) | 0.0028 (6) |
C8 | 0.0310 (7) | 0.0437 (8) | 0.0475 (8) | 0.0024 (6) | −0.0010 (6) | 0.0051 (7) |
C9 | 0.0418 (8) | 0.0454 (9) | 0.0564 (10) | −0.0066 (7) | 0.0025 (7) | −0.0064 (7) |
C10 | 0.0420 (8) | 0.0553 (10) | 0.0452 (9) | −0.0039 (7) | 0.0003 (7) | −0.0075 (7) |
Zn1—O1Wi | 2.0896 (11) | C2—C3 | 1.379 (3) |
Zn1—O1W | 2.0896 (11) | C2—H2A | 0.9300 |
Zn1—N1i | 2.1477 (13) | C3—C4 | 1.367 (3) |
Zn1—N1 | 2.1477 (13) | C3—H3A | 0.9300 |
Zn1—O1i | 2.1529 (10) | C4—C5 | 1.392 (2) |
Zn1—O1 | 2.1529 (10) | C4—H4A | 0.9300 |
S1—C8 | 1.7861 (16) | C5—C5i | 1.478 (4) |
S1—C7 | 1.8095 (15) | C6—C7 | 1.5247 (19) |
N1—C1 | 1.339 (2) | C7—H7A | 0.9700 |
N1—C5 | 1.3447 (19) | C7—H7B | 0.9700 |
O1W—H1WA | 0.825 (14) | C8—C9 | 1.382 (2) |
O1W—H1WB | 0.817 (14) | C8—C10 | 1.387 (2) |
O1—C6 | 1.2557 (16) | C9—C10ii | 1.388 (2) |
O2—C6 | 1.2506 (17) | C9—H9A | 0.9300 |
C1—C2 | 1.388 (3) | C10—C9ii | 1.388 (2) |
C1—H1A | 0.9300 | C10—H10A | 0.9300 |
O1Wi—Zn1—O1W | 98.69 (7) | C1—C2—H2A | 120.8 |
O1Wi—Zn1—N1i | 168.43 (5) | C4—C3—C2 | 119.51 (17) |
O1W—Zn1—N1i | 92.47 (5) | C4—C3—H3A | 120.2 |
O1Wi—Zn1—N1 | 92.47 (5) | C2—C3—H3A | 120.2 |
O1W—Zn1—N1 | 168.43 (5) | C3—C4—C5 | 119.63 (17) |
N1i—Zn1—N1 | 76.59 (7) | C3—C4—H4A | 120.2 |
O1Wi—Zn1—O1i | 86.70 (4) | C5—C4—H4A | 120.2 |
O1W—Zn1—O1i | 92.97 (4) | N1—C5—C4 | 121.03 (16) |
N1i—Zn1—O1i | 89.66 (4) | N1—C5—C5i | 115.91 (9) |
N1—Zn1—O1i | 90.74 (4) | C4—C5—C5i | 123.05 (11) |
O1Wi—Zn1—O1 | 92.97 (4) | O2—C6—O1 | 125.11 (13) |
O1W—Zn1—O1 | 86.70 (4) | O2—C6—C7 | 118.57 (12) |
N1i—Zn1—O1 | 90.74 (4) | O1—C6—C7 | 116.32 (12) |
N1—Zn1—O1 | 89.66 (4) | C6—C7—S1 | 114.48 (10) |
O1i—Zn1—O1 | 179.49 (5) | C6—C7—H7A | 108.6 |
C8—S1—C7 | 100.80 (7) | S1—C7—H7A | 108.6 |
C1—N1—C5 | 118.97 (14) | C6—C7—H7B | 108.6 |
C1—N1—Zn1 | 125.31 (11) | S1—C7—H7B | 108.6 |
C5—N1—Zn1 | 115.42 (11) | H7A—C7—H7B | 107.6 |
Zn1—O1W—H1WA | 127.8 (14) | C9—C8—C10 | 119.04 (15) |
Zn1—O1W—H1WB | 97.9 (14) | C9—C8—S1 | 120.80 (13) |
H1WA—O1W—H1WB | 104.3 (17) | C10—C8—S1 | 120.15 (13) |
C6—O1—Zn1 | 125.00 (9) | C8—C9—C10ii | 120.52 (16) |
N1—C1—C2 | 122.49 (17) | C8—C9—H9A | 119.7 |
N1—C1—H1A | 118.8 | C10ii—C9—H9A | 119.7 |
C2—C1—H1A | 118.8 | C8—C10—C9ii | 120.43 (16) |
C3—C2—C1 | 118.3 (2) | C8—C10—H10A | 119.8 |
C3—C2—H2A | 120.8 | C9ii—C10—H10A | 119.8 |
O1Wi—Zn1—N1—C1 | 7.41 (13) | C2—C3—C4—C5 | 0.0 (3) |
O1W—Zn1—N1—C1 | −157.1 (2) | C1—N1—C5—C4 | 2.5 (2) |
N1i—Zn1—N1—C1 | −176.39 (15) | Zn1—N1—C5—C4 | −171.45 (11) |
O1i—Zn1—N1—C1 | 94.13 (13) | C1—N1—C5—C5i | −178.37 (15) |
O1—Zn1—N1—C1 | −85.55 (13) | Zn1—N1—C5—C5i | 7.63 (19) |
O1Wi—Zn1—N1—C5 | −179.03 (10) | C3—C4—C5—N1 | −2.3 (2) |
O1W—Zn1—N1—C5 | 16.4 (3) | C3—C4—C5—C5i | 178.72 (18) |
N1i—Zn1—N1—C5 | −2.82 (7) | Zn1—O1—C6—O2 | 1.0 (2) |
O1i—Zn1—N1—C5 | −92.30 (10) | Zn1—O1—C6—C7 | −179.21 (9) |
O1—Zn1—N1—C5 | 88.01 (10) | O2—C6—C7—S1 | 51.79 (17) |
O1Wi—Zn1—O1—C6 | 63.39 (12) | O1—C6—C7—S1 | −128.01 (12) |
O1W—Zn1—O1—C6 | −35.15 (12) | C8—S1—C7—C6 | 55.61 (13) |
N1i—Zn1—O1—C6 | −127.58 (12) | C7—S1—C8—C9 | −80.93 (14) |
N1—Zn1—O1—C6 | 155.84 (12) | C7—S1—C8—C10 | 100.14 (14) |
O1i—Zn1—O1—C6 | 14.13 (13) | C10—C8—C9—C10ii | −1.0 (3) |
C5—N1—C1—C2 | −0.6 (2) | S1—C8—C9—C10ii | −179.94 (13) |
Zn1—N1—C1—C2 | 172.80 (13) | C9—C8—C10—C9ii | 1.0 (3) |
N1—C1—C2—C3 | −1.7 (3) | S1—C8—C10—C9ii | 179.95 (13) |
C1—C2—C3—C4 | 1.9 (3) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+3/2, −y+3/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2iii | 0.83 (1) | 1.90 (2) | 2.7107 (15) | 170 (2) |
O1W—H1WB···O2 | 0.82 (1) | 1.86 (2) | 2.6582 (16) | 164 (2) |
Symmetry code: (iii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C10H8O4S2)(C10H8N2)(H2O)2] |
Mr | 513.87 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 20.4396 (8), 12.8695 (8), 7.9798 (4) |
β (°) | 90.765 (3) |
V (Å3) | 2098.88 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.41 |
Crystal size (mm) | 0.22 × 0.16 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.761, 0.853 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16253, 2448, 2237 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.070, 1.04 |
No. of reflections | 2448 |
No. of parameters | 147 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.31 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2i | 0.825 (14) | 1.895 (15) | 2.7107 (15) | 169.7 (19) |
O1W—H1WB···O2 | 0.817 (14) | 1.862 (15) | 2.6582 (16) | 164 (2) |
Symmetry code: (i) x, −y+1, z−1/2. |
References
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, J., Yin, J. L., Wang, X. J. & Feng, Y. L. (2010). Chin. J. Inorg. Chem. 26, 1311–1314. CAS Google Scholar
Crystal Impact (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Jiang, Z. G., Wang, X. J., Yin, J. L., Feng, Y. L. & Cheng, J. W. (2012). Chin. J. Inorg. Chem. In the press. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göettingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X. J., Yin, J. L., Chen, J. & Feng, Y. L. (2011b). Chin. J. Inorg. Chem. 27, 367–371. CAS Google Scholar
Wang, X. J., Zhan, C. H., Feng, Y. L., Lan, Y. Z., Yin, J. L. & Cheng, J. W. (2011a). CrystEngComm, 13, 684–689. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, J.-L. & Feng, Y.-L. (2009). Acta Cryst. E65, o1206. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yin, J. L., Feng, Y. L. & Lan, Y. Z. (2009). Inorg. Chim. Acta, 362, 3769–3776. Web of Science CSD CrossRef CAS 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.
1,4-Benzenebis(thioacetic acid), (C10H10O4S2), is a flexible aromatic multi-carboxylate ligand, which can be prepared from 1,4-benzenebisthiol (Yin & Feng, 2009). Compared with rigid ligands, these flexible aromatic carboxylate ligands contain more coordination sites (viz. S and O atoms) to construct various extended structures with different metal ions. Recently, some complexes derived from 1,4-benzenebis(thioacetic acid) with bipyridine ligands have been reported (Yin et al., 2009; Chen et al., 2010; Wang et al., 2011a,b; Jiang et al., 2012). Here we report the synthesis and structure of a new complex, [Zn(C10H8O4S2)(C10H8N2)(H2O)2]n, (I).
Complex (I) is isotypic with its Co(II) analogue (Jiang et al., 2012). A view on the molecular structure of (I), showing the coordination environment of the Zn2+ ion, is presented in Fig. 1. The asymmetric unit consists of one Zn2+ ion (situated on a twofold rotation axis), half of a [C10H8O4S2]2- anion, half of a 2,2'-bipy molecule, and one coordinating water molecule. The Zn2+ ion is six-coordinated by two O atoms from two symmetry-related [C10H8O4S2]2- anions (Zn—O 2.1529 (10) Å), two N atoms from one chelating 2,2'-bipy molecule (Zn—N 2.1477 (13) Å), and two water molecules (Zn—O 2.0896 (11) Å) to form a slightly distorted octahedral geometry. The two pyridine rings in the bipy ligand are almost parallel with a dihedral angle of 11.5 (1)°. As shown in Fig. 2, adjacent Zn2+ ions are monodentately linked by the [C10H8O4S2]2- anions to form a chain structure running parallel to [101]. The chains are further linked by O—H···O hydrogen bonds to form the final three-dimensional supramolecular architecture (Fig. 3).