Acta Cryst. (2009). E65, m1640-m1641 [ doi:10.1107/S160053680904896X ]
![[mu]](/logos/entities/mu_rmgif.gif)
-2,4-dichloro-6-formylphenolato)bis[aqua(2,4-dichloro-6-formylphenolato)zinc(II)] (2/1)The crystal of the title compound, [Zn(C7H3Cl2O2)2(H2O)2]2·[Zn2(C7H3Cl2O2)4(H2O)2], consists of monomeric and dimeric ZnII complexes. Both complexes afford a six-coordinated coordination environment about the Zn atoms with cis-configuration ligands. The deprotonated hydroxy groups of the 3,5-dichlorosalicylaldehyde ligands bridge two metal cations, forming a centrosymmetric dimeric complex. Intermolecular O-H
O hydrogen bonding occurs between the coordinated water molecules and deprotonated hydroxy groups in the crystal structure.
Crystals were obtained accidentally as a byproduct of the treatment of 3,5-dichlorosalcylaldehyde (0.95 g, 5.00 mmol) in methanol (30 ml), L-alanine (0.44 g, 5.00 mmol) in water (5 ml), zinc(II) acetate dihydrate (0.55 g, 2.50 mmol) and several drops of triethylamine at c.a. 350 K for 2 hr.
Water-H atoms were located based on D-map and refined in riding mode. Other H atoms were placed at the calculated positions with C—H = 0.95 Å and refined in riding mode. Uiso(H) = 1.2Ueq(O,C).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008.
![[Figure 1]](./xu2645fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing the atom labeling scheme [symmetry code: (i) 2 - x, 1 - y, 2 - z]. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. |
| [Zn(C7H3Cl2O2)2(H2O)2]2·[Zn2(C7H3Cl2O2)4(H2O)2] | Z = 1 |
| Mr = 1889.61 | F(000) = 940.0 |
| Triclinic, P1 | Dx = 1.922 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.7532 (9) Å | Cell parameters from 2792 reflections |
| b = 13.6973 (15) Å | θ = 2.4–27.8° |
| c = 14.2833 (15) Å | µ = 2.19 mm−1 |
| α = 96.244 (2)° | T = 100 K |
| β = 91.700 (1)° | Prismatic, yellow |
| γ = 106.096 (1)° | 0.15 × 0.15 × 0.08 mm |
| V = 1632.4 (3) Å3 |
| Bruker APEXII CCD area-detector diffractometer | 7275 independent reflections |
| Radiation source: fine-focus sealed tube | 5671 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| Detector resolution: 8.333 pixels mm-1 | θmax = 27.9°, θmin = 1.4° |
| φ and ω scans | h = −11→11 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −16→17 |
| Tmin = 0.735, Tmax = 0.845 | l = −12→18 |
| 9504 measured reflections |
| 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.118 | H-atom parameters constrained |
| S = 0.75 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.2111P] where P = (Fo2 + 2Fc2)/3 |
| 7275 reflections | (Δ/σ)max = 0.001 |
| 445 parameters | Δρmax = 0.59 e Å−3 |
| 0 restraints | Δρmin = −0.46 e Å−3 |
| [Zn(C7H3Cl2O2)2(H2O)2]2·[Zn2(C7H3Cl2O2)4(H2O)2] | γ = 106.096 (1)° |
| Mr = 1889.61 | V = 1632.4 (3) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 8.7532 (9) Å | Mo Kα radiation |
| b = 13.6973 (15) Å | µ = 2.19 mm−1 |
| c = 14.2833 (15) Å | T = 100 K |
| α = 96.244 (2)° | 0.15 × 0.15 × 0.08 mm |
| β = 91.700 (1)° |
| Bruker APEXII CCD area-detector diffractometer | 7275 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5671 reflections with I > 2σ(I) |
| Tmin = 0.735, Tmax = 0.845 | Rint = 0.021 |
| 9504 measured reflections | θmax = 27.9° |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.118 | Δρmax = 0.59 e Å−3 |
| S = 0.75 | Δρmin = −0.46 e Å−3 |
| 7275 reflections | Absolute structure: ? |
| 445 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. 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. The water-H atoms wre located in a D-map and refined in riding mode with Uiso(H) = 1.2Ueq(O)." |
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. |
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.80461 (4) | 0.83299 (3) | 0.96067 (3) | 0.00981 (11) | |
| Zn2 | 0.92258 (4) | 0.39423 (3) | 0.93218 (3) | 0.00861 (10) | |
| C1 | 1.0506 (4) | 0.8558 (2) | 0.8153 (2) | 0.0115 (7) | |
| C2 | 1.2112 (4) | 0.8851 (2) | 0.7897 (2) | 0.0106 (7) | |
| C3 | 1.2547 (4) | 0.8968 (2) | 0.6987 (2) | 0.0114 (7) | |
| H3 | 1.3640 | 0.9165 | 0.6855 | 0.014* | |
| C4 | 1.1363 (4) | 0.8794 (3) | 0.6263 (2) | 0.0123 (7) | |
| C5 | 0.9784 (4) | 0.8516 (3) | 0.6459 (2) | 0.0144 (7) | |
| H5 | 0.8984 | 0.8400 | 0.5963 | 0.017* | |
| C6 | 0.9340 (4) | 0.8400 (2) | 0.7388 (2) | 0.0109 (7) | |
| C7 | 0.7636 (4) | 0.8084 (2) | 0.7507 (2) | 0.0122 (7) | |
| H7 | 0.6966 | 0.7972 | 0.6946 | 0.015* | |
| C8 | 0.8264 (4) | 0.8649 (2) | 1.1745 (2) | 0.0089 (6) | |
| C9 | 0.9119 (4) | 0.8798 (2) | 1.2634 (2) | 0.0111 (7) | |
| C10 | 0.8403 (4) | 0.8716 (3) | 1.3478 (2) | 0.0152 (7) | |
| H10C | 0.9029 | 0.8815 | 1.4053 | 0.018* | |
| C11 | 0.6749 (4) | 0.8485 (3) | 1.3479 (2) | 0.0140 (7) | |
| C12 | 0.5844 (4) | 0.8358 (3) | 1.2644 (2) | 0.0134 (7) | |
| H12 | 0.4719 | 0.8215 | 1.2653 | 0.016* | |
| C13 | 0.6573 (4) | 0.8437 (2) | 1.1784 (2) | 0.0105 (6) | |
| C14 | 0.5495 (4) | 0.8274 (2) | 1.0955 (2) | 0.0130 (7) | |
| H14 | 0.4403 | 0.8178 | 1.1070 | 0.016* | |
| C15 | 1.1453 (4) | 0.3785 (2) | 0.7795 (2) | 0.0105 (6) | |
| C16 | 1.3048 (4) | 0.3981 (2) | 0.7511 (2) | 0.0107 (7) | |
| C17 | 1.3436 (4) | 0.4026 (2) | 0.6585 (2) | 0.0119 (7) | |
| H17 | 1.4517 | 0.4171 | 0.6429 | 0.014* | |
| C18 | 1.2213 (4) | 0.3855 (3) | 0.5875 (2) | 0.0127 (7) | |
| C19 | 1.0649 (4) | 0.3623 (3) | 0.6098 (2) | 0.0133 (7) | |
| H19 | 0.9827 | 0.3478 | 0.5611 | 0.016* | |
| C20 | 1.0254 (4) | 0.3598 (2) | 0.7050 (2) | 0.0109 (6) | |
| C21 | 0.8572 (4) | 0.3365 (3) | 0.7224 (2) | 0.0130 (7) | |
| H21 | 0.7847 | 0.3167 | 0.6683 | 0.016* | |
| C22 | 0.9237 (4) | 0.4081 (2) | 1.1431 (2) | 0.0089 (6) | |
| C23 | 0.9985 (4) | 0.4002 (2) | 1.2300 (2) | 0.0103 (6) | |
| C24 | 0.9167 (4) | 0.3743 (2) | 1.3089 (2) | 0.0125 (7) | |
| H24 | 0.9724 | 0.3710 | 1.3660 | 0.015* | |
| C25 | 0.7501 (4) | 0.3529 (3) | 1.3036 (2) | 0.0120 (7) | |
| C26 | 0.6708 (4) | 0.3553 (2) | 1.2201 (2) | 0.0125 (7) | |
| H26 | 0.5578 | 0.3389 | 1.2166 | 0.015* | |
| C27 | 0.7539 (4) | 0.3816 (2) | 1.1396 (2) | 0.0097 (6) | |
| C28 | 0.6570 (4) | 0.3854 (2) | 1.0564 (2) | 0.0100 (6) | |
| H28 | 0.5461 | 0.3742 | 1.0636 | 0.012* | |
| O1 | 1.0177 (3) | 0.84419 (18) | 0.90218 (16) | 0.0114 (5) | |
| O2 | 0.6955 (3) | 0.79453 (18) | 0.82386 (17) | 0.0129 (5) | |
| O3 | 0.9021 (3) | 0.87169 (18) | 1.09647 (16) | 0.0120 (5) | |
| O4 | 0.5816 (3) | 0.82436 (18) | 1.01226 (16) | 0.0128 (5) | |
| O5 | 1.1173 (3) | 0.37770 (17) | 0.86854 (16) | 0.0107 (5) | |
| O6 | 0.7986 (3) | 0.33961 (18) | 0.79914 (16) | 0.0118 (5) | |
| O7 | 1.0093 (3) | 0.44105 (17) | 1.07188 (16) | 0.0090 (5) | |
| O8 | 0.7034 (3) | 0.40163 (17) | 0.97769 (16) | 0.0116 (5) | |
| Cl1 | 1.36080 (9) | 0.90539 (6) | 0.87857 (6) | 0.01455 (18) | |
| Cl2 | 1.19192 (11) | 0.89319 (7) | 0.51136 (6) | 0.0199 (2) | |
| Cl3 | 1.11849 (9) | 0.90686 (6) | 1.26347 (6) | 0.01406 (18) | |
| Cl4 | 0.58270 (11) | 0.83281 (7) | 1.45386 (6) | 0.0221 (2) | |
| Cl5 | 1.45564 (9) | 0.41888 (6) | 0.83825 (6) | 0.01241 (17) | |
| Cl6 | 1.27119 (11) | 0.39485 (7) | 0.47120 (6) | 0.0197 (2) | |
| Cl7 | 1.20508 (9) | 0.43012 (6) | 1.23861 (6) | 0.01256 (17) | |
| Cl8 | 0.64683 (11) | 0.32313 (7) | 1.40347 (6) | 0.0193 (2) | |
| O9 | 0.8187 (3) | 0.98658 (18) | 0.94441 (17) | 0.0133 (5) | |
| H9A | 0.9028 | 1.0128 | 0.9186 | 0.016* | |
| H9B | 0.8160 | 1.0363 | 0.9696 | 0.016* | |
| O10 | 0.7513 (3) | 0.67389 (17) | 0.97417 (17) | 0.0118 (5) | |
| H10A | 0.8109 | 0.6479 | 0.9410 | 0.014* | |
| H10B | 0.7730 | 0.6619 | 1.0275 | 0.014* | |
| O11 | 0.8612 (3) | 0.23683 (17) | 0.95443 (17) | 0.0120 (5) | |
| H11A | 0.9147 | 0.2065 | 0.9205 | 0.014* | |
| H11B | 0.8921 | 0.2170 | 1.0031 | 0.014* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.00838 (19) | 0.0114 (2) | 0.0092 (2) | 0.00159 (15) | −0.00065 (14) | 0.00263 (14) |
| Zn2 | 0.00720 (19) | 0.0103 (2) | 0.00819 (19) | 0.00178 (14) | −0.00008 (14) | 0.00230 (14) |
| C1 | 0.0112 (16) | 0.0069 (15) | 0.0166 (17) | 0.0020 (12) | 0.0003 (13) | 0.0044 (12) |
| C2 | 0.0133 (16) | 0.0074 (15) | 0.0109 (16) | 0.0028 (12) | −0.0022 (13) | 0.0019 (12) |
| C3 | 0.0106 (15) | 0.0103 (16) | 0.0142 (17) | 0.0030 (13) | 0.0036 (13) | 0.0046 (12) |
| C4 | 0.0169 (17) | 0.0127 (16) | 0.0072 (15) | 0.0031 (13) | 0.0053 (13) | 0.0025 (12) |
| C5 | 0.0153 (17) | 0.0101 (16) | 0.0164 (18) | 0.0016 (13) | −0.0022 (14) | 0.0021 (13) |
| C6 | 0.0109 (16) | 0.0094 (16) | 0.0104 (16) | −0.0005 (13) | 0.0010 (12) | 0.0019 (12) |
| C7 | 0.0117 (16) | 0.0118 (16) | 0.0123 (16) | 0.0022 (13) | −0.0021 (13) | 0.0021 (12) |
| C8 | 0.0136 (16) | 0.0064 (15) | 0.0076 (15) | 0.0044 (12) | 0.0010 (12) | 0.0007 (11) |
| C9 | 0.0113 (16) | 0.0074 (15) | 0.0152 (17) | 0.0033 (12) | 0.0016 (13) | 0.0029 (12) |
| C10 | 0.0176 (18) | 0.0165 (18) | 0.0106 (17) | 0.0037 (14) | −0.0013 (13) | 0.0011 (13) |
| C11 | 0.0158 (17) | 0.0128 (17) | 0.0137 (17) | 0.0034 (14) | 0.0057 (13) | 0.0027 (13) |
| C12 | 0.0098 (16) | 0.0130 (17) | 0.0156 (17) | −0.0006 (13) | 0.0025 (13) | 0.0039 (13) |
| C13 | 0.0110 (16) | 0.0089 (15) | 0.0120 (16) | 0.0029 (12) | −0.0001 (13) | 0.0024 (12) |
| C14 | 0.0080 (15) | 0.0112 (16) | 0.0184 (18) | 0.0001 (13) | −0.0010 (13) | 0.0029 (13) |
| C15 | 0.0124 (16) | 0.0087 (15) | 0.0097 (16) | 0.0018 (13) | −0.0003 (13) | 0.0012 (12) |
| C16 | 0.0103 (15) | 0.0084 (15) | 0.0108 (16) | −0.0012 (12) | −0.0027 (12) | 0.0009 (12) |
| C17 | 0.0084 (15) | 0.0118 (16) | 0.0134 (17) | 0.0006 (13) | 0.0002 (13) | −0.0007 (12) |
| C18 | 0.0176 (17) | 0.0127 (16) | 0.0075 (15) | 0.0033 (13) | 0.0047 (13) | 0.0013 (12) |
| C19 | 0.0111 (16) | 0.0173 (18) | 0.0113 (16) | 0.0044 (14) | −0.0025 (13) | 0.0017 (13) |
| C20 | 0.0104 (15) | 0.0113 (16) | 0.0128 (16) | 0.0051 (13) | 0.0028 (13) | 0.0025 (12) |
| C21 | 0.0097 (16) | 0.0137 (17) | 0.0138 (17) | 0.0009 (13) | −0.0028 (13) | 0.0015 (13) |
| C22 | 0.0107 (15) | 0.0043 (14) | 0.0090 (15) | −0.0026 (12) | 0.0003 (12) | 0.0017 (11) |
| C23 | 0.0091 (15) | 0.0090 (15) | 0.0111 (16) | −0.0005 (12) | −0.0031 (12) | 0.0023 (12) |
| C24 | 0.0157 (17) | 0.0088 (16) | 0.0130 (17) | 0.0030 (13) | −0.0010 (13) | 0.0031 (12) |
| C25 | 0.0136 (16) | 0.0101 (16) | 0.0118 (16) | 0.0007 (13) | 0.0044 (13) | 0.0052 (12) |
| C26 | 0.0092 (15) | 0.0098 (16) | 0.0174 (17) | 0.0014 (13) | 0.0033 (13) | −0.0003 (13) |
| C27 | 0.0103 (15) | 0.0061 (15) | 0.0103 (16) | −0.0009 (12) | −0.0013 (12) | −0.0006 (12) |
| C28 | 0.0057 (14) | 0.0124 (16) | 0.0100 (16) | 0.0006 (12) | 0.0007 (12) | −0.0014 (12) |
| O1 | 0.0089 (11) | 0.0191 (13) | 0.0080 (11) | 0.0054 (9) | 0.0018 (9) | 0.0048 (9) |
| O2 | 0.0097 (11) | 0.0143 (12) | 0.0140 (12) | 0.0018 (9) | 0.0000 (9) | 0.0032 (9) |
| O3 | 0.0105 (11) | 0.0133 (12) | 0.0108 (12) | 0.0006 (9) | 0.0001 (9) | 0.0030 (9) |
| O4 | 0.0106 (11) | 0.0154 (12) | 0.0124 (12) | 0.0039 (10) | −0.0012 (9) | 0.0015 (9) |
| O5 | 0.0103 (11) | 0.0127 (12) | 0.0103 (11) | 0.0039 (9) | 0.0001 (9) | 0.0045 (9) |
| O6 | 0.0068 (11) | 0.0156 (12) | 0.0123 (12) | 0.0012 (9) | −0.0003 (9) | 0.0036 (9) |
| O7 | 0.0069 (10) | 0.0107 (11) | 0.0083 (11) | 0.0006 (9) | 0.0000 (9) | 0.0023 (9) |
| O8 | 0.0091 (11) | 0.0133 (12) | 0.0129 (12) | 0.0038 (9) | −0.0004 (9) | 0.0018 (9) |
| Cl1 | 0.0096 (4) | 0.0199 (4) | 0.0140 (4) | 0.0040 (3) | −0.0021 (3) | 0.0026 (3) |
| Cl2 | 0.0194 (4) | 0.0286 (5) | 0.0104 (4) | 0.0033 (4) | 0.0041 (3) | 0.0053 (3) |
| Cl3 | 0.0105 (4) | 0.0191 (4) | 0.0124 (4) | 0.0037 (3) | −0.0011 (3) | 0.0028 (3) |
| Cl4 | 0.0225 (5) | 0.0287 (5) | 0.0146 (4) | 0.0045 (4) | 0.0097 (3) | 0.0060 (4) |
| Cl5 | 0.0082 (4) | 0.0159 (4) | 0.0121 (4) | 0.0018 (3) | −0.0015 (3) | 0.0022 (3) |
| Cl6 | 0.0197 (4) | 0.0279 (5) | 0.0089 (4) | 0.0024 (4) | 0.0032 (3) | 0.0020 (3) |
| Cl7 | 0.0089 (4) | 0.0177 (4) | 0.0105 (4) | 0.0020 (3) | −0.0008 (3) | 0.0043 (3) |
| Cl8 | 0.0196 (4) | 0.0249 (5) | 0.0147 (4) | 0.0052 (4) | 0.0092 (3) | 0.0084 (3) |
| O9 | 0.0118 (11) | 0.0118 (12) | 0.0164 (13) | 0.0028 (10) | 0.0007 (9) | 0.0038 (9) |
| O10 | 0.0104 (11) | 0.0145 (12) | 0.0112 (12) | 0.0046 (9) | −0.0006 (9) | 0.0026 (9) |
| O11 | 0.0118 (11) | 0.0128 (12) | 0.0133 (12) | 0.0057 (9) | 0.0012 (9) | 0.0042 (9) |
| Zn1—O1 | 2.040 (2) | C14—O4 | 1.229 (4) |
| Zn1—O2 | 2.096 (2) | C14—H14 | 0.9500 |
| Zn1—O3 | 2.049 (2) | C15—O5 | 1.303 (4) |
| Zn1—O4 | 2.084 (2) | C15—C20 | 1.422 (4) |
| Zn1—O9 | 2.112 (2) | C15—C16 | 1.426 (5) |
| Zn1—O10 | 2.130 (2) | C16—C17 | 1.379 (5) |
| Zn2—O5 | 2.011 (2) | C16—Cl5 | 1.730 (3) |
| Zn2—O6 | 2.114 (2) | C17—C18 | 1.405 (4) |
| Zn2—O7 | 2.081 (2) | C17—H17 | 0.9500 |
| Zn2—O7i | 2.176 (2) | C18—C19 | 1.373 (5) |
| Zn2—O8 | 2.069 (2) | C18—Cl6 | 1.739 (3) |
| Zn2—O11 | 2.134 (2) | C19—C20 | 1.415 (5) |
| C1—O1 | 1.298 (4) | C19—H19 | 0.9500 |
| C1—C2 | 1.422 (5) | C20—C21 | 1.452 (5) |
| C1—C6 | 1.429 (4) | C21—O6 | 1.226 (4) |
| C2—C3 | 1.378 (5) | C21—H21 | 0.9500 |
| C2—Cl1 | 1.739 (3) | C22—O7 | 1.327 (4) |
| C3—C4 | 1.395 (5) | C22—C23 | 1.415 (4) |
| C3—H3 | 0.9500 | C22—C27 | 1.427 (4) |
| C4—C5 | 1.374 (5) | C23—C24 | 1.378 (5) |
| C4—Cl2 | 1.741 (3) | C23—Cl7 | 1.737 (3) |
| C5—C6 | 1.407 (5) | C24—C25 | 1.404 (5) |
| C5—H5 | 0.9500 | C24—H24 | 0.9500 |
| C6—C7 | 1.454 (5) | C25—C26 | 1.370 (5) |
| C7—O2 | 1.225 (4) | C25—Cl8 | 1.736 (3) |
| C7—H7 | 0.9500 | C26—C27 | 1.406 (5) |
| C8—O3 | 1.313 (4) | C26—H26 | 0.9500 |
| C8—C9 | 1.419 (4) | C27—C28 | 1.453 (4) |
| C8—C13 | 1.431 (4) | C28—O8 | 1.228 (4) |
| C9—C10 | 1.376 (5) | C28—H28 | 0.9500 |
| C9—Cl3 | 1.743 (3) | O7—Zn2i | 2.176 (2) |
| C10—C11 | 1.393 (5) | O9—H9A | 0.8400 |
| C10—H10C | 0.9500 | O9—H9B | 0.7416 |
| C11—C12 | 1.379 (5) | O10—H10A | 0.8400 |
| C11—Cl4 | 1.743 (4) | O10—H10B | 0.8234 |
| C12—C13 | 1.403 (5) | O11—H11A | 0.8400 |
| C12—H12 | 0.9500 | O11—H11B | 0.8371 |
| C13—C14 | 1.449 (4) | ||
| O1—Zn1—O3 | 94.50 (9) | C12—C13—C14 | 115.3 (3) |
| O1—Zn1—O4 | 176.22 (8) | C8—C13—C14 | 123.4 (3) |
| O3—Zn1—O4 | 88.77 (9) | O4—C14—C13 | 128.2 (3) |
| O1—Zn1—O2 | 87.95 (9) | O4—C14—H14 | 115.9 |
| O3—Zn1—O2 | 177.47 (10) | C13—C14—H14 | 115.9 |
| O4—Zn1—O2 | 88.76 (9) | O5—C15—C20 | 124.4 (3) |
| O1—Zn1—O9 | 91.79 (10) | O5—C15—C16 | 120.1 (3) |
| O3—Zn1—O9 | 92.35 (9) | C20—C15—C16 | 115.5 (3) |
| O4—Zn1—O9 | 86.17 (9) | C17—C16—C15 | 123.2 (3) |
| O2—Zn1—O9 | 86.93 (9) | C17—C16—Cl5 | 119.1 (3) |
| O1—Zn1—O10 | 95.85 (9) | C15—C16—Cl5 | 117.7 (2) |
| O3—Zn1—O10 | 91.64 (9) | C16—C17—C18 | 119.2 (3) |
| O4—Zn1—O10 | 85.94 (9) | C16—C17—H17 | 120.4 |
| O2—Zn1—O10 | 88.74 (9) | C18—C17—H17 | 120.4 |
| O9—Zn1—O10 | 171.08 (9) | C19—C18—C17 | 120.4 (3) |
| O5—Zn2—O8 | 171.11 (9) | C19—C18—Cl6 | 120.6 (3) |
| O5—Zn2—O7 | 102.25 (9) | C17—C18—Cl6 | 119.0 (3) |
| O8—Zn2—O7 | 86.59 (9) | C18—C19—C20 | 120.3 (3) |
| O5—Zn2—O6 | 86.25 (9) | C18—C19—H19 | 119.8 |
| O8—Zn2—O6 | 84.87 (9) | C20—C19—H19 | 119.8 |
| O7—Zn2—O6 | 170.91 (9) | C19—C20—C15 | 121.2 (3) |
| O5—Zn2—O11 | 89.56 (9) | C19—C20—C21 | 116.7 (3) |
| O8—Zn2—O11 | 89.17 (9) | C15—C20—C21 | 122.1 (3) |
| O7—Zn2—O11 | 91.76 (9) | O6—C21—C20 | 127.1 (3) |
| O6—Zn2—O11 | 85.01 (9) | O6—C21—H21 | 116.4 |
| O5—Zn2—O7i | 93.02 (9) | C20—C21—H21 | 116.4 |
| O8—Zn2—O7i | 89.27 (9) | O7—C22—C23 | 120.8 (3) |
| O7—Zn2—O7i | 81.32 (9) | O7—C22—C27 | 123.6 (3) |
| O6—Zn2—O7i | 101.65 (8) | C23—C22—C27 | 115.6 (3) |
| O11—Zn2—O7i | 172.99 (9) | C24—C23—C22 | 123.5 (3) |
| O1—C1—C2 | 120.8 (3) | C24—C23—Cl7 | 118.6 (2) |
| O1—C1—C6 | 124.5 (3) | C22—C23—Cl7 | 117.9 (3) |
| C2—C1—C6 | 114.7 (3) | C23—C24—C25 | 119.2 (3) |
| C3—C2—C1 | 123.8 (3) | C23—C24—H24 | 120.4 |
| C3—C2—Cl1 | 118.4 (3) | C25—C24—H24 | 120.4 |
| C1—C2—Cl1 | 117.7 (2) | C26—C25—C24 | 119.9 (3) |
| C2—C3—C4 | 119.3 (3) | C26—C25—Cl8 | 120.8 (3) |
| C2—C3—H3 | 120.4 | C24—C25—Cl8 | 119.4 (3) |
| C4—C3—H3 | 120.4 | C25—C26—C27 | 121.1 (3) |
| C5—C4—C3 | 120.1 (3) | C25—C26—H26 | 119.4 |
| C5—C4—Cl2 | 120.9 (3) | C27—C26—H26 | 119.4 |
| C3—C4—Cl2 | 119.0 (3) | C26—C27—C22 | 120.7 (3) |
| C4—C5—C6 | 120.7 (3) | C26—C27—C28 | 115.9 (3) |
| C4—C5—H5 | 119.7 | C22—C27—C28 | 123.3 (3) |
| C6—C5—H5 | 119.7 | O8—C28—C27 | 126.8 (3) |
| C5—C6—C1 | 121.4 (3) | O8—C28—H28 | 116.6 |
| C5—C6—C7 | 115.7 (3) | C27—C28—H28 | 116.6 |
| C1—C6—C7 | 122.9 (3) | C1—O1—Zn1 | 127.5 (2) |
| O2—C7—C6 | 128.1 (3) | C7—O2—Zn1 | 125.6 (2) |
| O2—C7—H7 | 116.0 | C8—O3—Zn1 | 127.4 (2) |
| C6—C7—H7 | 116.0 | C14—O4—Zn1 | 126.4 (2) |
| O3—C8—C9 | 120.5 (3) | C15—O5—Zn2 | 128.2 (2) |
| O3—C8—C13 | 124.5 (3) | C21—O6—Zn2 | 126.7 (2) |
| C9—C8—C13 | 115.0 (3) | C22—O7—Zn2 | 121.66 (19) |
| C10—C9—C8 | 123.7 (3) | C22—O7—Zn2i | 115.7 (2) |
| C10—C9—Cl3 | 119.1 (3) | Zn2—O7—Zn2i | 98.68 (9) |
| C8—C9—Cl3 | 117.2 (3) | C28—O8—Zn2 | 124.9 (2) |
| C9—C10—C11 | 119.2 (3) | Zn1—O9—H9A | 109.5 |
| C9—C10—H10C | 120.4 | Zn1—O9—H9B | 144.2 |
| C11—C10—H10C | 120.4 | H9A—O9—H9B | 93.4 |
| C12—C11—C10 | 120.3 (3) | Zn1—O10—H10A | 109.5 |
| C12—C11—Cl4 | 120.1 (3) | Zn1—O10—H10B | 113.6 |
| C10—C11—Cl4 | 119.6 (3) | H10A—O10—H10B | 102.5 |
| C11—C12—C13 | 120.4 (3) | Zn2—O11—H11A | 109.5 |
| C11—C12—H12 | 119.8 | Zn2—O11—H11B | 122.7 |
| C13—C12—H12 | 119.8 | H11A—O11—H11B | 91.6 |
| C12—C13—C8 | 121.3 (3) | ||
| O1—C1—C2—C3 | 178.7 (3) | C23—C24—C25—Cl8 | −178.5 (3) |
| C6—C1—C2—C3 | −0.8 (5) | C24—C25—C26—C27 | −1.7 (5) |
| O1—C1—C2—Cl1 | −0.3 (4) | Cl8—C25—C26—C27 | 178.5 (3) |
| C6—C1—C2—Cl1 | −179.8 (2) | C25—C26—C27—C22 | −1.0 (5) |
| C1—C2—C3—C4 | 0.1 (5) | C25—C26—C27—C28 | −177.6 (3) |
| Cl1—C2—C3—C4 | 179.0 (3) | O7—C22—C27—C26 | −174.7 (3) |
| C2—C3—C4—C5 | 0.4 (5) | C23—C22—C27—C26 | 3.4 (5) |
| C2—C3—C4—Cl2 | −179.4 (3) | O7—C22—C27—C28 | 1.7 (5) |
| C3—C4—C5—C6 | −0.2 (5) | C23—C22—C27—C28 | 179.8 (3) |
| Cl2—C4—C5—C6 | 179.7 (3) | C26—C27—C28—O8 | −176.2 (3) |
| C4—C5—C6—C1 | −0.6 (5) | C22—C27—C28—O8 | 7.3 (5) |
| C4—C5—C6—C7 | −178.9 (3) | C2—C1—O1—Zn1 | 165.8 (2) |
| O1—C1—C6—C5 | −178.4 (3) | C6—C1—O1—Zn1 | −14.8 (5) |
| C2—C1—C6—C5 | 1.0 (5) | O3—Zn1—O1—C1 | −160.0 (3) |
| O1—C1—C6—C7 | −0.3 (5) | O2—Zn1—O1—C1 | 19.3 (3) |
| C2—C1—C6—C7 | 179.2 (3) | O9—Zn1—O1—C1 | −67.5 (3) |
| C5—C6—C7—O2 | −179.0 (3) | O10—Zn1—O1—C1 | 107.9 (3) |
| C1—C6—C7—O2 | 2.7 (6) | C6—C7—O2—Zn1 | 9.7 (5) |
| O3—C8—C9—C10 | −178.5 (3) | O1—Zn1—O2—C7 | −16.7 (3) |
| C13—C8—C9—C10 | 2.1 (5) | O4—Zn1—O2—C7 | 161.5 (3) |
| O3—C8—C9—Cl3 | −0.1 (4) | O9—Zn1—O2—C7 | 75.2 (3) |
| C13—C8—C9—Cl3 | −179.5 (2) | O10—Zn1—O2—C7 | −112.6 (3) |
| C8—C9—C10—C11 | −0.7 (5) | C9—C8—O3—Zn1 | 170.2 (2) |
| Cl3—C9—C10—C11 | −179.1 (3) | C13—C8—O3—Zn1 | −10.4 (4) |
| C9—C10—C11—C12 | −1.1 (5) | O1—Zn1—O3—C8 | −169.0 (3) |
| C9—C10—C11—Cl4 | 177.4 (3) | O4—Zn1—O3—C8 | 12.9 (3) |
| C10—C11—C12—C13 | 1.4 (5) | O9—Zn1—O3—C8 | 99.0 (3) |
| Cl4—C11—C12—C13 | −177.1 (3) | O10—Zn1—O3—C8 | −73.0 (3) |
| C11—C12—C13—C8 | 0.2 (5) | C13—C14—O4—Zn1 | 4.1 (5) |
| C11—C12—C13—C14 | 179.1 (3) | O3—Zn1—O4—C14 | −9.8 (3) |
| O3—C8—C13—C12 | 178.8 (3) | O2—Zn1—O4—C14 | 170.7 (3) |
| C9—C8—C13—C12 | −1.8 (4) | O9—Zn1—O4—C14 | −102.2 (3) |
| O3—C8—C13—C14 | −0.1 (5) | O10—Zn1—O4—C14 | 81.9 (3) |
| C9—C8—C13—C14 | 179.3 (3) | C20—C15—O5—Zn2 | −20.6 (5) |
| C12—C13—C14—O4 | −175.5 (3) | C16—C15—O5—Zn2 | 160.1 (2) |
| C8—C13—C14—O4 | 3.4 (5) | O7—Zn2—O5—C15 | −158.3 (3) |
| O5—C15—C16—C17 | −178.4 (3) | O6—Zn2—O5—C15 | 24.9 (3) |
| C20—C15—C16—C17 | 2.2 (5) | O11—Zn2—O5—C15 | 110.0 (3) |
| O5—C15—C16—Cl5 | 0.7 (4) | O7i—Zn2—O5—C15 | −76.5 (3) |
| C20—C15—C16—Cl5 | −178.7 (2) | C20—C21—O6—Zn2 | 6.7 (5) |
| C15—C16—C17—C18 | −1.1 (5) | O5—Zn2—O6—C21 | −18.1 (3) |
| Cl5—C16—C17—C18 | 179.8 (3) | O8—Zn2—O6—C21 | 162.4 (3) |
| C16—C17—C18—C19 | −1.5 (5) | O11—Zn2—O6—C21 | −108.0 (3) |
| C16—C17—C18—Cl6 | 178.2 (3) | O7i—Zn2—O6—C21 | 74.2 (3) |
| C17—C18—C19—C20 | 2.8 (5) | C23—C22—O7—Zn2 | 151.4 (2) |
| Cl6—C18—C19—C20 | −176.8 (3) | C27—C22—O7—Zn2 | −30.6 (4) |
| C18—C19—C20—C15 | −1.6 (5) | C23—C22—O7—Zn2i | −89.0 (3) |
| C18—C19—C20—C21 | 178.8 (3) | C27—C22—O7—Zn2i | 89.0 (3) |
| O5—C15—C20—C19 | 179.8 (3) | O5—Zn2—O7—C22 | −141.2 (2) |
| C16—C15—C20—C19 | −0.8 (5) | O8—Zn2—O7—C22 | 37.8 (2) |
| O5—C15—C20—C21 | −0.7 (5) | O11—Zn2—O7—C22 | −51.2 (2) |
| C16—C15—C20—C21 | 178.7 (3) | O7i—Zn2—O7—C22 | 127.6 (3) |
| C19—C20—C21—O6 | −172.9 (3) | O5—Zn2—O7—Zn2i | 91.22 (10) |
| C15—C20—C21—O6 | 7.6 (5) | O8—Zn2—O7—Zn2i | −89.78 (9) |
| O7—C22—C23—C24 | 174.7 (3) | O11—Zn2—O7—Zn2i | −178.85 (9) |
| C27—C22—C23—C24 | −3.4 (5) | O7i—Zn2—O7—Zn2i | 0.0 |
| O7—C22—C23—Cl7 | −2.5 (4) | C27—C28—O8—Zn2 | 15.4 (5) |
| C27—C22—C23—Cl7 | 179.4 (2) | O7—Zn2—O8—C28 | −31.0 (3) |
| C22—C23—C24—C25 | 1.0 (5) | O6—Zn2—O8—C28 | 145.8 (3) |
| Cl7—C23—C24—C25 | 178.1 (3) | O11—Zn2—O8—C28 | 60.8 (3) |
| C23—C24—C25—C26 | 1.7 (5) | O7i—Zn2—O8—C28 | −112.4 (3) |
| Symmetry codes: (i) −x+2, −y+1, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O9—H9A···O3ii | 0.84 | 2.02 | 2.790 (3) | 153 |
| O9—H9B···O1ii | 0.74 | 2.45 | 3.015 (3) | 134 |
| O10—H10A···O7i | 0.84 | 2.24 | 2.998 (3) | 150 |
| O10—H10B···O5i | 0.82 | 1.95 | 2.741 (3) | 161 |
| O11—H11A···O3i | 0.84 | 2.17 | 2.931 (3) | 151 |
| O11—H11B···O1i | 0.84 | 1.93 | 2.751 (3) | 169 |
| Symmetry codes: (ii) −x+2, −y+2, −z+2; (i) −x+2, −y+1, −z+2. |
| Zn1—O1 | 2.040 (2) | Zn2—O5 | 2.011 (2) |
| Zn1—O2 | 2.096 (2) | Zn2—O6 | 2.114 (2) |
| Zn1—O3 | 2.049 (2) | Zn2—O7 | 2.081 (2) |
| Zn1—O4 | 2.084 (2) | Zn2—O7i | 2.176 (2) |
| Zn1—O9 | 2.112 (2) | Zn2—O8 | 2.069 (2) |
| Zn1—O10 | 2.130 (2) | Zn2—O11 | 2.134 (2) |
| Symmetry codes: (i) −x+2, −y+1, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O9—H9A···O3ii | 0.84 | 2.02 | 2.790 (3) | 153 |
| O9—H9B···O1ii | 0.74 | 2.45 | 3.015 (3) | 134 |
| O10—H10A···O7i | 0.84 | 2.24 | 2.998 (3) | 150 |
| O10—H10B···O5i | 0.82 | 1.95 | 2.741 (3) | 161 |
| O11—H11A···O3i | 0.84 | 2.17 | 2.931 (3) | 151 |
| O11—H11B···O1i | 0.84 | 1.93 | 2.751 (3) | 169 |
| Symmetry codes: (ii) −x+2, −y+2, −z+2; (i) −x+2, −y+1, −z+2. |
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3,5-Dichlorosalcylaldehydato plays an important role in preparation of Schiff base metal complexes because of electronic properties due to Cl-groups for example supramolecular interactions between metallodendrimers (Akitsu et al., 2009) or photochromic compounds (Akitsu & Einaga, 2005a & 2005b; Akitsu, 2007). Depending on amine reagents and their steric requirement, trans (Akitsu & Einaga, 2004a & 2004b) or cis (Akitsu et al., 2005) forms of complexes can be formed. However, we focused on only 3,5-dichloroaldehyde moiety to elucidate structural features without amine moiety.
The title compound (I) is composed of a co-crystal of monomeric [Zn(C7H3Cl2O2)2(H2O)2] and dimeric [Zn(C7H3Cl2O2)2(H2O)]. Both complexes afford a six-coordinated coordination environment exhibiting significant distortion. In contrast to known zinc(II) complexes incorporating saldehyde-derivertive ligands (Chen, 2006; Chen et al., 2007; Xiong & Liu, 2005), both ligands bind to Zn(II) ions in a cis-configuration for (I).