metal-organic compounds
catena-Poly[[[dibromidocadmium]-μ2-1,1′-(butane-1,4-diyl)bis(pyridinium-4-carboxylate)] monohydrate]
aThe Institute of Higher Education, Changchun Normal University, Changchun 130032, People's Republic of China, and bCollege of Chemistry, Changchun Normal University, Changchun 130032, People's Republic of China
*Correspondence e-mail: rzchen2011@yahoo.cn
In the title compound, {[CdBr2(C16H16N2O4)]·H2O}n, the CdII ion is six-coordinated by a Br2O4 donor set, with four O atoms from two bridging 1,1′-(butane-1,4-diyl)bis(pyridinium-4-carboxylate) ligands. The ligands link the CdII ions into a zigzag chain extending along [01]. O—H⋯O and O—H⋯Br hydrogen bonds involving the uncoordinated water molecules connect the chains.
Related literature
For the design and synthesis of coordination polymers, see: Li et al. (2005). For a related structure, see: Ma et al. (2000).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); 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 (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S160053681101662X/hy2426sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681101662X/hy2426Isup2.hkl
The ligand L was synthesized according to literature (Li et al., 2005). A mixture of Cd(NO3)2.4H2O (0.015 g), L (0.023 g), NaOH (0.004 g) and water (10 ml) was heated at 80°C for 25 min. After the mixture had been cooled to room temperature, colorless crystals of the title compound were obtained (yield: 43%).
H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.97 (CH2) Å and with Uiso(H)= 1.2Ueq(C). Water H atoms were located in a difference Fourier map and refined with a restraint of O—H = 0.84 (1) Å and with Uiso(H) = 1.5Ueq(O). The highest residual electron density was found at 0.33 Å from Cd1 atom and the deepest hole at 0.37 Å from Br2 atom.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[CdBr2(C16H16N2O4)]·H2O | Z = 2 |
Mr = 590.53 | F(000) = 572 |
Triclinic, P1 | Dx = 2.130 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6529 (5) Å | Cell parameters from 3238 reflections |
b = 9.3969 (6) Å | θ = 1.5–26.2° |
c = 14.0198 (9) Å | µ = 5.56 mm−1 |
α = 74.410 (1)° | T = 296 K |
β = 87.060 (2)° | Block, colorless |
γ = 71.581 (1)° | 0.20 × 0.17 × 0.16 mm |
V = 920.75 (10) Å3 |
Bruker APEX CCD diffractometer | 3600 independent reflections |
Radiation source: fine-focus sealed tube | 3238 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ϕ and ω scans | θmax = 26.2°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.34, Tmax = 0.41 | k = −7→11 |
5114 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: patterson |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0524P)2 + 9.2463P] where P = (Fo2 + 2Fc2)/3 |
3600 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 1.45 e Å−3 |
4 restraints | Δρmin = −2.11 e Å−3 |
[CdBr2(C16H16N2O4)]·H2O | γ = 71.581 (1)° |
Mr = 590.53 | V = 920.75 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6529 (5) Å | Mo Kα radiation |
b = 9.3969 (6) Å | µ = 5.56 mm−1 |
c = 14.0198 (9) Å | T = 296 K |
α = 74.410 (1)° | 0.20 × 0.17 × 0.16 mm |
β = 87.060 (2)° |
Bruker APEX CCD diffractometer | 3600 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3238 reflections with I > 2σ(I) |
Tmin = 0.34, Tmax = 0.41 | Rint = 0.013 |
5114 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 4 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.45 e Å−3 |
3600 reflections | Δρmin = −2.11 e Å−3 |
241 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.47375 (5) | 1.16457 (5) | 0.24196 (3) | 0.01263 (13) | |
C1 | 0.7499 (8) | 0.9542 (7) | 0.3709 (4) | 0.0134 (11) | |
C2 | 1.1656 (8) | 0.6169 (7) | 0.4914 (4) | 0.0131 (11) | |
H4 | 1.2521 | 0.5317 | 0.4764 | 0.016* | |
C3 | 1.0287 (8) | 0.7160 (7) | 0.4228 (4) | 0.0149 (11) | |
H3 | 1.0244 | 0.6995 | 0.3606 | 0.018* | |
C4 | 0.8966 (8) | 0.8412 (7) | 0.4467 (4) | 0.0130 (11) | |
C5 | 0.9054 (8) | 0.8616 (7) | 0.5403 (4) | 0.0142 (11) | |
H6 | 0.8164 | 0.9424 | 0.5585 | 0.017* | |
C6 | 1.0467 (8) | 0.7616 (6) | 0.6065 (4) | 0.0129 (11) | |
H5 | 1.0537 | 0.7760 | 0.6691 | 0.015* | |
C7 | 1.3272 (8) | 0.5417 (7) | 0.6535 (4) | 0.0136 (11) | |
H7A | 1.3690 | 0.6045 | 0.6861 | 0.016* | |
H7B | 1.4298 | 0.4894 | 0.6187 | 0.016* | |
C8 | 1.2649 (8) | 0.4214 (7) | 0.7305 (4) | 0.0144 (11) | |
H8A | 1.2521 | 0.3430 | 0.7008 | 0.017* | |
H8B | 1.1457 | 0.4711 | 0.7539 | 0.017* | |
C9 | 1.4043 (8) | 0.3444 (7) | 0.8174 (4) | 0.0135 (11) | |
H9A | 1.5276 | 0.3192 | 0.7923 | 0.016* | |
H9B | 1.3945 | 0.4173 | 0.8565 | 0.016* | |
C10 | 1.3755 (8) | 0.1972 (7) | 0.8834 (4) | 0.0135 (11) | |
H10A | 1.3859 | 0.1243 | 0.8442 | 0.016* | |
H10B | 1.4723 | 0.1495 | 0.9349 | 0.016* | |
C11 | 1.1690 (8) | 0.2881 (7) | 1.0082 (4) | 0.0157 (12) | |
H11 | 1.2593 | 0.3246 | 1.0254 | 0.019* | |
C12 | 1.0140 (8) | 0.2988 (7) | 1.0617 (4) | 0.0154 (11) | |
H12 | 0.9988 | 0.3416 | 1.1153 | 0.019* | |
C13 | 0.8779 (8) | 0.2448 (6) | 1.0353 (4) | 0.0127 (11) | |
C14 | 0.9010 (8) | 0.1903 (7) | 0.9516 (4) | 0.0138 (11) | |
H14 | 0.8086 | 0.1604 | 0.9299 | 0.017* | |
C15 | 1.0608 (8) | 0.1803 (7) | 0.9003 (4) | 0.0144 (11) | |
H15 | 1.0771 | 0.1422 | 0.8446 | 0.017* | |
C16 | 0.7200 (8) | 0.2339 (7) | 1.1034 (4) | 0.0146 (11) | |
N1 | 1.1736 (7) | 0.6442 (6) | 0.5809 (3) | 0.0123 (9) | |
N2 | 1.1936 (6) | 0.2255 (5) | 0.9307 (3) | 0.0103 (9) | |
O1 | 0.7496 (6) | 0.9313 (5) | 0.2877 (3) | 0.0158 (8) | |
O2 | 0.6345 (6) | 1.0670 (5) | 0.3958 (3) | 0.0169 (9) | |
O3 | 0.6036 (6) | 0.1791 (5) | 1.0807 (3) | 0.0171 (9) | |
O4 | 0.7215 (6) | 0.2727 (5) | 1.1822 (3) | 0.0181 (9) | |
Br1 | 0.24542 (9) | 1.43346 (8) | 0.24021 (6) | 0.0306 (2) | |
Br2 | 0.26563 (10) | 0.98804 (8) | 0.25061 (5) | 0.02913 (19) | |
O1W | 0.4919 (7) | 0.2586 (5) | 0.5341 (3) | 0.0234 (10) | |
H1A | 0.529 (11) | 0.199 (8) | 0.497 (5) | 0.035* | |
H1B | 0.539 (11) | 0.207 (9) | 0.590 (3) | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0110 (2) | 0.0143 (2) | 0.0108 (2) | −0.00276 (16) | 0.00083 (14) | −0.00187 (15) |
C1 | 0.015 (3) | 0.014 (3) | 0.013 (3) | −0.008 (2) | 0.001 (2) | −0.002 (2) |
C2 | 0.015 (3) | 0.014 (3) | 0.012 (3) | −0.006 (2) | 0.001 (2) | −0.004 (2) |
C3 | 0.019 (3) | 0.016 (3) | 0.011 (3) | −0.007 (2) | 0.001 (2) | −0.005 (2) |
C4 | 0.013 (3) | 0.014 (3) | 0.014 (3) | −0.007 (2) | 0.001 (2) | −0.003 (2) |
C5 | 0.015 (3) | 0.014 (3) | 0.014 (3) | −0.004 (2) | 0.004 (2) | −0.005 (2) |
C6 | 0.017 (3) | 0.011 (3) | 0.010 (3) | −0.004 (2) | 0.003 (2) | −0.003 (2) |
C7 | 0.012 (3) | 0.017 (3) | 0.011 (3) | −0.005 (2) | −0.002 (2) | 0.000 (2) |
C8 | 0.011 (3) | 0.014 (3) | 0.016 (3) | −0.006 (2) | −0.001 (2) | 0.001 (2) |
C9 | 0.013 (3) | 0.015 (3) | 0.011 (3) | −0.005 (2) | 0.001 (2) | 0.000 (2) |
C10 | 0.011 (3) | 0.015 (3) | 0.012 (3) | −0.002 (2) | 0.003 (2) | −0.003 (2) |
C11 | 0.016 (3) | 0.020 (3) | 0.013 (3) | −0.009 (2) | 0.000 (2) | −0.004 (2) |
C12 | 0.017 (3) | 0.017 (3) | 0.013 (3) | −0.004 (2) | 0.001 (2) | −0.005 (2) |
C13 | 0.014 (3) | 0.009 (3) | 0.012 (3) | −0.002 (2) | 0.000 (2) | −0.001 (2) |
C14 | 0.016 (3) | 0.013 (3) | 0.011 (3) | −0.005 (2) | −0.003 (2) | −0.001 (2) |
C15 | 0.015 (3) | 0.014 (3) | 0.014 (3) | −0.005 (2) | 0.000 (2) | −0.003 (2) |
C16 | 0.015 (3) | 0.012 (3) | 0.014 (3) | −0.002 (2) | 0.001 (2) | −0.002 (2) |
N1 | 0.015 (2) | 0.012 (2) | 0.010 (2) | −0.0066 (19) | 0.0010 (18) | −0.0004 (18) |
N2 | 0.012 (2) | 0.010 (2) | 0.008 (2) | −0.0035 (18) | 0.0005 (17) | 0.0000 (17) |
O1 | 0.017 (2) | 0.017 (2) | 0.012 (2) | −0.0024 (17) | −0.0020 (16) | −0.0040 (16) |
O2 | 0.020 (2) | 0.017 (2) | 0.012 (2) | −0.0018 (17) | −0.0011 (16) | −0.0040 (16) |
O3 | 0.014 (2) | 0.026 (2) | 0.012 (2) | −0.0086 (18) | 0.0017 (15) | −0.0031 (17) |
O4 | 0.017 (2) | 0.025 (2) | 0.015 (2) | −0.0080 (18) | 0.0052 (16) | −0.0081 (18) |
Br1 | 0.0196 (3) | 0.0228 (4) | 0.0477 (5) | −0.0041 (3) | 0.0005 (3) | −0.0095 (3) |
Br2 | 0.0287 (4) | 0.0294 (4) | 0.0303 (4) | −0.0093 (3) | 0.0054 (3) | −0.0102 (3) |
O1W | 0.030 (3) | 0.018 (2) | 0.020 (2) | −0.005 (2) | 0.0032 (19) | −0.0052 (18) |
Cd1—O1 | 2.476 (4) | C8—H8A | 0.9700 |
Cd1—O2 | 2.345 (4) | C8—H8B | 0.9700 |
Cd1—O3i | 2.409 (4) | C9—C10 | 1.518 (8) |
Cd1—O4i | 2.435 (4) | C9—H9A | 0.9700 |
Cd1—Br1 | 2.5728 (8) | C9—H9B | 0.9700 |
Cd1—Br2 | 2.6162 (8) | C10—N2 | 1.487 (7) |
C1—O1 | 1.241 (7) | C10—H10A | 0.9700 |
C1—O2 | 1.266 (7) | C10—H10B | 0.9700 |
C1—C4 | 1.510 (8) | C11—N2 | 1.347 (7) |
C2—N1 | 1.354 (7) | C11—C12 | 1.361 (8) |
C2—C3 | 1.377 (8) | C11—H11 | 0.9300 |
C2—H4 | 0.9300 | C12—C13 | 1.398 (8) |
C3—C4 | 1.394 (8) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.385 (8) |
C4—C5 | 1.383 (8) | C13—C16 | 1.513 (8) |
C5—C6 | 1.380 (8) | C14—C15 | 1.376 (8) |
C5—H6 | 0.9300 | C14—H14 | 0.9300 |
C6—N1 | 1.338 (7) | C15—N2 | 1.345 (7) |
C6—H5 | 0.9300 | C15—H15 | 0.9300 |
C7—N1 | 1.491 (7) | C16—O3 | 1.252 (7) |
C7—C8 | 1.517 (8) | C16—O4 | 1.254 (7) |
C7—H7A | 0.9700 | O1W—H1A | 0.84 (7) |
C7—H7B | 0.9700 | O1W—H1B | 0.83 (5) |
C8—C9 | 1.522 (8) | ||
O2—Cd1—O3i | 127.10 (14) | C8—C7—H7B | 109.5 |
O2—Cd1—O4i | 86.07 (15) | H7A—C7—H7B | 108.1 |
O3i—Cd1—O4i | 54.49 (14) | C7—C8—C9 | 110.3 (5) |
O2—Cd1—O1 | 54.51 (14) | C7—C8—H8A | 109.6 |
O3i—Cd1—O1 | 81.38 (14) | C9—C8—H8A | 109.6 |
O4i—Cd1—O1 | 78.10 (14) | C7—C8—H8B | 109.6 |
O2—Cd1—Br1 | 106.91 (10) | C9—C8—H8B | 109.6 |
O3i—Cd1—Br1 | 108.36 (11) | H8A—C8—H8B | 108.1 |
O4i—Cd1—Br1 | 92.51 (10) | C10—C9—C8 | 112.4 (5) |
O1—Cd1—Br1 | 159.25 (10) | C10—C9—H9A | 109.1 |
O2—Cd1—Br2 | 104.34 (11) | C8—C9—H9A | 109.1 |
O3i—Cd1—Br2 | 103.49 (10) | C10—C9—H9B | 109.1 |
O4i—Cd1—Br2 | 156.16 (10) | C8—C9—H9B | 109.1 |
O1—Cd1—Br2 | 90.43 (10) | H9A—C9—H9B | 107.8 |
Br1—Cd1—Br2 | 104.48 (3) | N2—C10—C9 | 113.1 (5) |
O2—Cd1—C16i | 106.48 (16) | N2—C10—H10A | 108.9 |
O3i—Cd1—C16i | 27.25 (16) | C9—C10—H10A | 108.9 |
O4i—Cd1—C16i | 27.32 (16) | N2—C10—H10B | 108.9 |
O1—Cd1—C16i | 76.82 (15) | C9—C10—H10B | 108.9 |
Br1—Cd1—C16i | 103.21 (12) | H10A—C10—H10B | 107.8 |
Br2—Cd1—C16i | 129.79 (12) | N2—C11—C12 | 121.1 (5) |
O2—Cd1—C1 | 27.52 (16) | N2—C11—H11 | 119.5 |
O3i—Cd1—C1 | 104.69 (16) | C12—C11—H11 | 119.5 |
O4i—Cd1—C1 | 81.35 (16) | C11—C12—C13 | 119.4 (5) |
O1—Cd1—C1 | 26.99 (15) | C11—C12—H12 | 120.3 |
Br1—Cd1—C1 | 133.92 (12) | C13—C12—H12 | 120.3 |
Br2—Cd1—C1 | 97.91 (12) | C14—C13—C12 | 118.4 (5) |
C16i—Cd1—C1 | 91.88 (17) | C14—C13—C16 | 122.0 (5) |
O1—C1—O2 | 123.8 (5) | C12—C13—C16 | 119.3 (5) |
O1—C1—C4 | 118.2 (5) | C15—C14—C13 | 120.0 (5) |
O2—C1—C4 | 118.0 (5) | C15—C14—H14 | 120.0 |
O1—C1—Cd1 | 64.9 (3) | C13—C14—H14 | 120.0 |
O2—C1—Cd1 | 58.9 (3) | N2—C15—C14 | 120.1 (5) |
C4—C1—Cd1 | 176.8 (4) | N2—C15—H15 | 120.0 |
N1—C2—C3 | 119.7 (5) | C14—C15—H15 | 120.0 |
N1—C2—H4 | 120.2 | O3—C16—O4 | 124.4 (6) |
C3—C2—H4 | 120.2 | O3—C16—C13 | 118.5 (5) |
C2—C3—C4 | 119.9 (5) | O4—C16—C13 | 116.9 (5) |
C2—C3—H3 | 120.1 | O3—C16—Cd1ii | 61.8 (3) |
C4—C3—H3 | 120.1 | O4—C16—Cd1ii | 63.0 (3) |
C5—C4—C3 | 118.7 (5) | C13—C16—Cd1ii | 170.2 (4) |
C5—C4—C1 | 120.9 (5) | C6—N1—C2 | 121.7 (5) |
C3—C4—C1 | 120.4 (5) | C6—N1—C7 | 118.6 (5) |
C6—C5—C4 | 119.7 (5) | C2—N1—C7 | 119.8 (5) |
C6—C5—H6 | 120.1 | C15—N2—C11 | 120.8 (5) |
C4—C5—H6 | 120.1 | C15—N2—C10 | 120.3 (5) |
N1—C6—C5 | 120.3 (5) | C11—N2—C10 | 118.7 (5) |
N1—C6—H5 | 119.9 | C1—O1—Cd1 | 88.1 (3) |
C5—C6—H5 | 119.9 | C1—O2—Cd1 | 93.6 (3) |
N1—C7—C8 | 110.8 (4) | C16—O3—Cd1ii | 90.9 (3) |
N1—C7—H7A | 109.5 | C16—O4—Cd1ii | 89.7 (4) |
C8—C7—H7A | 109.5 | H1A—O1W—H1B | 105 (8) |
N1—C7—H7B | 109.5 |
Symmetry codes: (i) x, y+1, z−1; (ii) x, y−1, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2iii | 0.84 (7) | 2.10 (7) | 2.934 (6) | 174 (5) |
O1W—H1B···Br2iv | 0.83 (5) | 2.65 (6) | 3.467 (4) | 169 (6) |
Symmetry codes: (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [CdBr2(C16H16N2O4)]·H2O |
Mr | 590.53 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.6529 (5), 9.3969 (6), 14.0198 (9) |
α, β, γ (°) | 74.410 (1), 87.060 (2), 71.581 (1) |
V (Å3) | 920.75 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 5.56 |
Crystal size (mm) | 0.20 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.34, 0.41 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5114, 3600, 3238 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.620 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.118, 1.08 |
No. of reflections | 3600 |
No. of parameters | 241 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.45, −2.11 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).
Cd1—O1 | 2.476 (4) | Cd1—O4i | 2.435 (4) |
Cd1—O2 | 2.345 (4) | Cd1—Br1 | 2.5728 (8) |
Cd1—O3i | 2.409 (4) | Cd1—Br2 | 2.6162 (8) |
Symmetry code: (i) x, y+1, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2ii | 0.84 (7) | 2.10 (7) | 2.934 (6) | 174 (5) |
O1W—H1B···Br2iii | 0.83 (5) | 2.65 (6) | 3.467 (4) | 169 (6) |
Symmetry codes: (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
We thank Changchun Normal University for support.
References
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The design and synthesis of coordination polymers are of great interest for their intriguing architectures and potential applications (Li et al., 2005). In this paper, the structure of the title compound is described.
As shown in Fig. 1, the CdII ion is six-coordinated by two Br- anions and four O atoms from two butane-1,4-diylbis(pyridinium-1-yl-4-carboxylate (L) ligands (Table 1). The two carboxylate groups of the L ligand display a bidentate chelating mode. The bond distances and angles are normal (Ma et al., 2000). As illustrated in Fig. 2, each L ligand bridges two CdII ions, resulting in a one-dimensional zigzag chain, with a Cd···Cd separation of 14.630 (1) Å. O—H···O and O—H···Br hydrogen bonds (Table 2) involving the uncoordinated water molecules connect the chains.