

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040937/om2150sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040937/om2150Isup2.hkl |
CCDC reference: 660157
A mixture of Zn(NO3)2.6H2O (0.1 mmol), phen (0.1 mmol), 5-chlorosalicylic acid (0.2 mmol) and distilled water (10 ml) was put into a Teflon-lined autoclave (20 ml) and then heated at 413 K for 72 h. Colorless block-like crystals suitable for X-ray analysis were collected from the reaction mixture.
The aromatic H atoms were positioned geometrically and were included in the refinement in the riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C)]. The water H atoms were found in a difference Fourier map and were refined with distance restraints of O—H = 0.85 (1)Å and Uiso(H) = 1.2 Ueq(O).
A lot of attention has been paid to the metal salicylate owing to their intriguing structural features (Brownless et al., 1999; Lemoine et al., 2002; Zhu et al., 2003; Yin et al., 2004; Wen et al., 2007a,b,c) and biological applications (Lemoine et al., 2004). We report here the structure of a Zn (II) complex with 5-chloroosalicylate ligand (Melnik et al., 2001). The title complex, Zn(C7H4ClO3)2(C12H8N2)(H2O) was synthesized under hydrothermal conditions. The Zn atom is coordinated in a distorted trigonal bipyramid geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from one 1,10-phenanthroline and one water O atom (Fig. 1). One Zn—N bond is significantly shorter than the other (Zn1—N1 = 2.099 (2) Å, Zn1—N2 = 2.160 (2) Å). These distances are comparable to the Zn—N bond lengths (Zn—N1 = 2.109 (3) Å, Zn—N2 = 2.178 (3) Å) in [Zn(ta)(phen)(H2O)]n (Sun et al., 2001). The complex has rich hydrogen bonds formed by the coordinated water molecule, hydroxy and carboxyl O atoms (Fig. 2). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds interactions (Fig. 3).
For related literature, see: Brownless et al. (1999); Lemoine et al. (2002, 2004); Melnik et al. (2001); Sun et al. (2001); Wen et al. (2007a,b,c); Yin et al. (2004); Zhu et al. (2003).
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Zn(C7H4ClO3)2(C12H8N2)(H2O)] | Z = 2 |
Mr = 606.69 | F(000) = 616 |
Triclinic, P1 | Dx = 1.644 Mg m−3 |
a = 8.681 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.777 (6) Å | Cell parameters from 5553 reflections |
c = 12.982 (9) Å | θ = 3.2–27.5° |
α = 72.06 (2)° | µ = 1.27 mm−1 |
β = 76.98 (2)° | T = 293 K |
γ = 81.592 (19)° | Block, colourless |
V = 1225.9 (12) Å3 | 0.28 × 0.26 × 0.25 mm |
Rigaku R-AXIS RAPID Weissenberg IP diffractometer | 4462 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −11→9 |
12131 measured reflections | k = −15→14 |
5553 independent reflections | l = −16→16 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0162P)2 + 0.2964P] where P = (Fo2 + 2Fc2)/3 |
5553 reflections | (Δ/σ)max = 0.002 |
355 parameters | Δρmax = 0.54 e Å−3 |
4 restraints | Δρmin = −0.44 e Å−3 |
[Zn(C7H4ClO3)2(C12H8N2)(H2O)] | γ = 81.592 (19)° |
Mr = 606.69 | V = 1225.9 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.681 (4) Å | Mo Kα radiation |
b = 11.777 (6) Å | µ = 1.27 mm−1 |
c = 12.982 (9) Å | T = 293 K |
α = 72.06 (2)° | 0.28 × 0.26 × 0.25 mm |
β = 76.98 (2)° |
Rigaku R-AXIS RAPID Weissenberg IP diffractometer | 4462 reflections with I > 2σ(I) |
12131 measured reflections | Rint = 0.049 |
5553 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 4 restraints |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.54 e Å−3 |
5553 reflections | Δρmin = −0.44 e Å−3 |
355 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 | 0.64074 (3) | 0.98442 (2) | 0.813250 (19) | 0.03415 (9) | |
N1 | 0.5901 (2) | 1.07549 (15) | 0.65649 (14) | 0.0353 (4) | |
N2 | 0.8038 (2) | 0.88896 (14) | 0.71017 (14) | 0.0333 (4) | |
O1 | 0.7926 (2) | 1.09096 (14) | 0.81791 (15) | 0.0494 (4) | |
O2 | 0.7919 (2) | 1.05973 (15) | 0.99631 (15) | 0.0510 (4) | |
O3 | 0.9882 (2) | 1.15930 (17) | 1.05330 (15) | 0.0578 (5) | |
H3A | 0.917 (2) | 1.115 (2) | 1.058 (3) | 0.069* | |
O4 | 0.57974 (18) | 0.83560 (12) | 0.93499 (11) | 0.0373 (3) | |
O5 | 0.4509 (2) | 0.80266 (16) | 0.81983 (14) | 0.0563 (5) | |
O6 | 0.2744 (3) | 0.6264 (2) | 0.8834 (2) | 0.0726 (6) | |
H6A | 0.317 (4) | 0.6903 (18) | 0.843 (3) | 0.087* | |
C1 | 0.9516 (2) | 1.20453 (18) | 0.86614 (18) | 0.0348 (5) | |
C2 | 1.0224 (3) | 1.2225 (2) | 0.9464 (2) | 0.0418 (5) | |
C3 | 1.1299 (3) | 1.3083 (2) | 0.9158 (2) | 0.0527 (6) | |
H3 | 1.1788 | 1.3186 | 0.9688 | 0.063* | |
C4 | 1.1657 (3) | 1.3782 (2) | 0.8093 (3) | 0.0540 (7) | |
H4 | 1.2380 | 1.4358 | 0.7900 | 0.065* | |
C5 | 1.0934 (3) | 1.3625 (2) | 0.7307 (2) | 0.0423 (5) | |
C6 | 0.9881 (3) | 1.27671 (19) | 0.75859 (19) | 0.0385 (5) | |
H6 | 0.9407 | 1.2669 | 0.7047 | 0.046* | |
C7 | 0.8372 (2) | 1.11091 (19) | 0.8966 (2) | 0.0380 (5) | |
C8 | 0.4146 (2) | 0.67431 (18) | 1.00260 (18) | 0.0359 (5) | |
C9 | 0.3112 (3) | 0.6059 (2) | 0.9838 (2) | 0.0502 (6) | |
C10 | 0.2413 (3) | 0.5146 (2) | 1.0708 (3) | 0.0643 (8) | |
H10 | 0.1718 | 0.4693 | 1.0586 | 0.077* | |
C11 | 0.2734 (3) | 0.4907 (2) | 1.1739 (3) | 0.0660 (9) | |
H11 | 0.2261 | 0.4293 | 1.2315 | 0.079* | |
C12 | 0.3758 (3) | 0.5577 (2) | 1.1922 (2) | 0.0522 (7) | |
C13 | 0.4467 (3) | 0.64840 (19) | 1.10822 (18) | 0.0400 (5) | |
H13 | 0.5164 | 0.6926 | 1.1218 | 0.048* | |
C14 | 0.4861 (2) | 0.77654 (18) | 0.91259 (17) | 0.0356 (5) | |
C15 | 0.4887 (3) | 1.1706 (2) | 0.63063 (19) | 0.0463 (6) | |
H15 | 0.4287 | 1.2009 | 0.6868 | 0.056* | |
C16 | 0.4683 (3) | 1.2270 (2) | 0.5230 (2) | 0.0529 (6) | |
H16 | 0.3968 | 1.2942 | 0.5080 | 0.064* | |
C17 | 0.5538 (3) | 1.1834 (2) | 0.4396 (2) | 0.0501 (6) | |
H17 | 0.5398 | 1.2196 | 0.3674 | 0.060* | |
C18 | 0.6633 (3) | 1.0831 (2) | 0.46356 (18) | 0.0400 (5) | |
C19 | 0.7607 (3) | 1.0325 (2) | 0.38123 (19) | 0.0489 (6) | |
H19 | 0.7508 | 1.0655 | 0.3078 | 0.059* | |
C20 | 0.8664 (3) | 0.9377 (2) | 0.40863 (19) | 0.0497 (6) | |
H20 | 0.9288 | 0.9068 | 0.3536 | 0.060* | |
C21 | 0.8846 (3) | 0.8841 (2) | 0.52007 (18) | 0.0403 (5) | |
C22 | 0.9915 (3) | 0.7849 (2) | 0.5542 (2) | 0.0495 (6) | |
H22 | 1.0534 | 0.7483 | 0.5030 | 0.059* | |
C23 | 1.0045 (3) | 0.7421 (2) | 0.6625 (2) | 0.0481 (6) | |
H23 | 1.0762 | 0.6771 | 0.6854 | 0.058* | |
C24 | 0.9086 (3) | 0.79723 (19) | 0.73877 (19) | 0.0408 (5) | |
H24 | 0.9190 | 0.7683 | 0.8123 | 0.049* | |
C25 | 0.7908 (2) | 0.93152 (17) | 0.60344 (17) | 0.0324 (4) | |
C26 | 0.6781 (2) | 1.03261 (18) | 0.57349 (17) | 0.0331 (4) | |
Cl1 | 1.13591 (10) | 1.45253 (6) | 0.59530 (6) | 0.0686 (2) | |
Cl2 | 0.41211 (12) | 0.52968 (9) | 1.32473 (7) | 0.0937 (3) | |
O7 | 0.4401 (2) | 1.07947 (14) | 0.88416 (13) | 0.0429 (4) | |
H7B | 0.364 (2) | 1.0363 (18) | 0.915 (2) | 0.051* | |
H7A | 0.455 (3) | 1.108 (2) | 0.9330 (17) | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.04762 (15) | 0.03512 (13) | 0.01979 (12) | −0.01181 (11) | −0.00212 (10) | −0.00721 (9) |
N1 | 0.0421 (9) | 0.0392 (9) | 0.0238 (9) | −0.0076 (9) | −0.0023 (7) | −0.0088 (7) |
N2 | 0.0397 (9) | 0.0355 (9) | 0.0251 (9) | −0.0125 (8) | −0.0022 (7) | −0.0080 (7) |
O1 | 0.0595 (10) | 0.0475 (9) | 0.0518 (11) | −0.0156 (8) | −0.0167 (8) | −0.0198 (8) |
O2 | 0.0553 (10) | 0.0515 (9) | 0.0451 (11) | −0.0131 (8) | 0.0009 (8) | −0.0158 (8) |
O3 | 0.0748 (13) | 0.0657 (11) | 0.0397 (10) | −0.0093 (10) | −0.0192 (9) | −0.0176 (9) |
O4 | 0.0483 (8) | 0.0349 (7) | 0.0252 (8) | −0.0110 (7) | −0.0010 (6) | −0.0045 (6) |
O5 | 0.0710 (11) | 0.0678 (11) | 0.0312 (9) | −0.0140 (10) | −0.0138 (8) | −0.0091 (8) |
O6 | 0.0778 (14) | 0.0823 (14) | 0.0773 (17) | −0.0227 (12) | −0.0165 (12) | −0.0426 (13) |
C1 | 0.0333 (10) | 0.0362 (10) | 0.0398 (12) | 0.0021 (10) | −0.0085 (9) | −0.0189 (9) |
C2 | 0.0433 (12) | 0.0470 (12) | 0.0422 (13) | 0.0039 (11) | −0.0148 (10) | −0.0214 (10) |
C3 | 0.0488 (13) | 0.0626 (15) | 0.0601 (18) | −0.0070 (13) | −0.0238 (13) | −0.0262 (13) |
C4 | 0.0394 (12) | 0.0540 (15) | 0.075 (2) | −0.0095 (12) | −0.0121 (13) | −0.0238 (14) |
C5 | 0.0390 (11) | 0.0421 (11) | 0.0443 (14) | −0.0016 (11) | −0.0036 (10) | −0.0140 (10) |
C6 | 0.0407 (11) | 0.0408 (11) | 0.0390 (13) | 0.0030 (10) | −0.0111 (10) | −0.0191 (9) |
C7 | 0.0369 (11) | 0.0359 (11) | 0.0447 (13) | 0.0020 (10) | −0.0072 (10) | −0.0193 (10) |
C8 | 0.0355 (10) | 0.0312 (10) | 0.0383 (12) | −0.0037 (9) | 0.0003 (9) | −0.0108 (9) |
C9 | 0.0462 (13) | 0.0470 (13) | 0.0644 (18) | −0.0048 (12) | −0.0034 (12) | −0.0308 (12) |
C10 | 0.0592 (16) | 0.0442 (14) | 0.092 (2) | −0.0211 (13) | 0.0075 (16) | −0.0305 (15) |
C11 | 0.0615 (17) | 0.0361 (12) | 0.080 (2) | −0.0152 (13) | 0.0175 (16) | −0.0048 (13) |
C12 | 0.0478 (13) | 0.0418 (12) | 0.0498 (16) | −0.0025 (12) | 0.0020 (12) | 0.0030 (11) |
C13 | 0.0378 (11) | 0.0344 (10) | 0.0391 (13) | −0.0056 (10) | −0.0013 (10) | −0.0010 (9) |
C14 | 0.0403 (11) | 0.0352 (10) | 0.0278 (11) | −0.0007 (10) | 0.0006 (9) | −0.0101 (8) |
C15 | 0.0538 (14) | 0.0479 (13) | 0.0333 (13) | −0.0008 (12) | −0.0040 (11) | −0.0106 (10) |
C16 | 0.0602 (15) | 0.0522 (13) | 0.0382 (14) | 0.0050 (13) | −0.0103 (12) | −0.0049 (11) |
C17 | 0.0609 (15) | 0.0576 (14) | 0.0280 (12) | −0.0115 (13) | −0.0120 (11) | −0.0013 (10) |
C18 | 0.0502 (12) | 0.0466 (12) | 0.0243 (11) | −0.0162 (11) | −0.0030 (9) | −0.0090 (9) |
C19 | 0.0664 (15) | 0.0598 (14) | 0.0225 (11) | −0.0184 (14) | −0.0031 (11) | −0.0123 (10) |
C20 | 0.0644 (15) | 0.0596 (14) | 0.0286 (12) | −0.0140 (14) | 0.0037 (11) | −0.0228 (11) |
C21 | 0.0490 (12) | 0.0443 (12) | 0.0314 (12) | −0.0130 (11) | 0.0007 (10) | −0.0179 (9) |
C22 | 0.0536 (14) | 0.0497 (13) | 0.0484 (15) | −0.0070 (12) | 0.0026 (12) | −0.0265 (11) |
C23 | 0.0503 (13) | 0.0420 (12) | 0.0535 (16) | −0.0020 (12) | −0.0094 (12) | −0.0170 (11) |
C24 | 0.0477 (12) | 0.0376 (11) | 0.0373 (13) | −0.0105 (11) | −0.0076 (10) | −0.0081 (9) |
C25 | 0.0376 (10) | 0.0357 (10) | 0.0261 (10) | −0.0160 (9) | 0.0004 (8) | −0.0110 (8) |
C26 | 0.0401 (11) | 0.0382 (10) | 0.0228 (10) | −0.0163 (10) | −0.0012 (8) | −0.0089 (8) |
Cl1 | 0.0842 (5) | 0.0558 (4) | 0.0535 (4) | −0.0097 (4) | 0.0007 (4) | −0.0062 (3) |
Cl2 | 0.1015 (6) | 0.1024 (6) | 0.0450 (4) | −0.0271 (5) | −0.0060 (4) | 0.0281 (4) |
O7 | 0.0572 (10) | 0.0429 (8) | 0.0263 (8) | −0.0089 (8) | 0.0018 (7) | −0.0116 (6) |
Zn1—O1 | 1.9706 (18) | C9—C10 | 1.390 (4) |
Zn1—O4 | 2.0094 (17) | C10—C11 | 1.364 (5) |
Zn1—N1 | 2.099 (2) | C10—H10 | 0.9300 |
Zn1—O7 | 2.1154 (17) | C11—C12 | 1.373 (4) |
Zn1—N2 | 2.1599 (18) | C11—H11 | 0.9300 |
N1—C15 | 1.325 (3) | C12—C13 | 1.372 (3) |
N1—C26 | 1.361 (3) | C12—Cl2 | 1.741 (3) |
N2—C24 | 1.323 (3) | C13—H13 | 0.9300 |
N2—C25 | 1.345 (3) | C15—C16 | 1.389 (3) |
O1—C7 | 1.265 (3) | C15—H15 | 0.9300 |
O2—C7 | 1.247 (3) | C16—C17 | 1.363 (3) |
O3—C2 | 1.346 (3) | C16—H16 | 0.9300 |
O3—H3A | 0.847 (10) | C17—C18 | 1.404 (3) |
O4—C14 | 1.275 (3) | C17—H17 | 0.9300 |
O5—C14 | 1.244 (3) | C18—C26 | 1.395 (3) |
O6—C9 | 1.354 (4) | C18—C19 | 1.432 (3) |
O6—H6A | 0.854 (10) | C19—C20 | 1.348 (3) |
C1—C6 | 1.386 (3) | C19—H19 | 0.9300 |
C1—C2 | 1.404 (3) | C20—C21 | 1.424 (3) |
C1—C7 | 1.494 (3) | C20—H20 | 0.9300 |
C2—C3 | 1.383 (4) | C21—C22 | 1.404 (3) |
C3—C4 | 1.366 (4) | C21—C25 | 1.410 (3) |
C3—H3 | 0.9300 | C22—C23 | 1.365 (4) |
C4—C5 | 1.382 (4) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—C24 | 1.400 (3) |
C5—C6 | 1.372 (3) | C23—H23 | 0.9300 |
C5—Cl1 | 1.738 (3) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C26 | 1.439 (3) |
C8—C13 | 1.393 (3) | O7—H7B | 0.844 (10) |
C8—C9 | 1.395 (3) | O7—H7A | 0.847 (10) |
C8—C14 | 1.492 (3) | ||
O1—Zn1—O4 | 123.68 (8) | C10—C11—H11 | 120.2 |
O1—Zn1—N1 | 98.46 (8) | C12—C11—H11 | 120.2 |
O4—Zn1—N1 | 137.84 (7) | C13—C12—C11 | 121.0 (3) |
O1—Zn1—O7 | 94.31 (8) | C13—C12—Cl2 | 119.5 (2) |
O4—Zn1—O7 | 88.75 (7) | C11—C12—Cl2 | 119.5 (2) |
N1—Zn1—O7 | 89.25 (7) | C12—C13—C8 | 120.1 (2) |
O1—Zn1—N2 | 96.73 (8) | C12—C13—H13 | 120.0 |
O4—Zn1—N2 | 94.37 (7) | C8—C13—H13 | 120.0 |
N1—Zn1—N2 | 78.09 (8) | O5—C14—O4 | 122.4 (2) |
O7—Zn1—N2 | 164.28 (7) | O5—C14—C8 | 119.6 (2) |
C15—N1—C26 | 118.14 (19) | O4—C14—C8 | 117.99 (19) |
C15—N1—Zn1 | 127.30 (15) | N1—C15—C16 | 122.7 (2) |
C26—N1—Zn1 | 114.49 (14) | N1—C15—H15 | 118.6 |
C24—N2—C25 | 118.49 (18) | C16—C15—H15 | 118.6 |
C24—N2—Zn1 | 128.86 (15) | C17—C16—C15 | 119.6 (2) |
C25—N2—Zn1 | 112.65 (13) | C17—C16—H16 | 120.2 |
C7—O1—Zn1 | 132.72 (17) | C15—C16—H16 | 120.2 |
C2—O3—H3A | 106 (2) | C16—C17—C18 | 119.4 (2) |
C14—O4—Zn1 | 113.35 (13) | C16—C17—H17 | 120.3 |
C9—O6—H6A | 106 (3) | C18—C17—H17 | 120.3 |
C6—C1—C2 | 118.6 (2) | C26—C18—C17 | 117.4 (2) |
C6—C1—C7 | 120.8 (2) | C26—C18—C19 | 119.1 (2) |
C2—C1—C7 | 120.6 (2) | C17—C18—C19 | 123.4 (2) |
O3—C2—C3 | 118.3 (2) | C20—C19—C18 | 120.9 (2) |
O3—C2—C1 | 122.1 (2) | C20—C19—H19 | 119.5 |
C3—C2—C1 | 119.5 (2) | C18—C19—H19 | 119.5 |
C4—C3—C2 | 121.2 (2) | C19—C20—C21 | 121.4 (2) |
C4—C3—H3 | 119.4 | C19—C20—H20 | 119.3 |
C2—C3—H3 | 119.4 | C21—C20—H20 | 119.3 |
C3—C4—C5 | 119.3 (3) | C22—C21—C25 | 116.4 (2) |
C3—C4—H4 | 120.3 | C22—C21—C20 | 124.2 (2) |
C5—C4—H4 | 120.3 | C25—C21—C20 | 119.3 (2) |
C6—C5—C4 | 120.5 (2) | C23—C22—C21 | 120.1 (2) |
C6—C5—Cl1 | 119.76 (19) | C23—C22—H22 | 120.0 |
C4—C5—Cl1 | 119.7 (2) | C21—C22—H22 | 120.0 |
C5—C6—C1 | 120.8 (2) | C22—C23—C24 | 119.2 (2) |
C5—C6—H6 | 119.6 | C22—C23—H23 | 120.4 |
C1—C6—H6 | 119.6 | C24—C23—H23 | 120.4 |
O2—C7—O1 | 125.1 (2) | N2—C24—C23 | 122.5 (2) |
O2—C7—C1 | 118.2 (2) | N2—C24—H24 | 118.7 |
O1—C7—C1 | 116.7 (2) | C23—C24—H24 | 118.7 |
C13—C8—C9 | 119.0 (2) | N2—C25—C21 | 123.3 (2) |
C13—C8—C14 | 120.0 (2) | N2—C25—C26 | 117.74 (17) |
C9—C8—C14 | 121.0 (2) | C21—C25—C26 | 118.9 (2) |
O6—C9—C10 | 118.5 (3) | N1—C26—C18 | 122.7 (2) |
O6—C9—C8 | 122.1 (2) | N1—C26—C25 | 116.99 (19) |
C10—C9—C8 | 119.4 (3) | C18—C26—C25 | 120.32 (18) |
C11—C10—C9 | 120.9 (3) | Zn1—O7—H7B | 112.3 (16) |
C11—C10—H10 | 119.6 | Zn1—O7—H7A | 115.6 (17) |
C9—C10—H10 | 119.6 | H7B—O7—H7A | 105 (3) |
C10—C11—C12 | 119.6 (3) | ||
O1—Zn1—N1—C15 | −81.8 (2) | C10—C11—C12—C13 | −0.1 (4) |
O4—Zn1—N1—C15 | 99.7 (2) | C10—C11—C12—Cl2 | 178.2 (2) |
O7—Zn1—N1—C15 | 12.4 (2) | C11—C12—C13—C8 | 0.4 (3) |
N2—Zn1—N1—C15 | −177.0 (2) | Cl2—C12—C13—C8 | −177.89 (16) |
O1—Zn1—N1—C26 | 95.23 (15) | C9—C8—C13—C12 | −0.8 (3) |
O4—Zn1—N1—C26 | −83.21 (17) | C14—C8—C13—C12 | 177.21 (19) |
O7—Zn1—N1—C26 | −170.52 (15) | Zn1—O4—C14—O5 | 7.2 (2) |
N2—Zn1—N1—C26 | 0.08 (14) | Zn1—O4—C14—C8 | −171.40 (13) |
O1—Zn1—N2—C24 | 82.48 (19) | C13—C8—C14—O5 | −176.59 (19) |
O4—Zn1—N2—C24 | −42.21 (19) | C9—C8—C14—O5 | 1.3 (3) |
N1—Zn1—N2—C24 | 179.75 (19) | C13—C8—C14—O4 | 2.1 (3) |
O7—Zn1—N2—C24 | −143.2 (2) | C9—C8—C14—O4 | −179.99 (17) |
O1—Zn1—N2—C25 | −98.22 (15) | C26—N1—C15—C16 | 0.5 (4) |
O4—Zn1—N2—C25 | 137.10 (14) | Zn1—N1—C15—C16 | 177.5 (2) |
N1—Zn1—N2—C25 | −0.95 (14) | N1—C15—C16—C17 | 0.7 (4) |
O7—Zn1—N2—C25 | 36.1 (3) | C15—C16—C17—C18 | −1.1 (4) |
O4—Zn1—O1—C7 | −24.4 (2) | C16—C17—C18—C26 | 0.3 (4) |
N1—Zn1—O1—C7 | 156.85 (18) | C16—C17—C18—C19 | −178.7 (2) |
O7—Zn1—O1—C7 | 66.96 (19) | C26—C18—C19—C20 | −0.4 (4) |
N2—Zn1—O1—C7 | −124.25 (19) | C17—C18—C19—C20 | 178.5 (2) |
O1—Zn1—O4—C14 | −176.53 (12) | C18—C19—C20—C21 | 0.4 (4) |
N1—Zn1—O4—C14 | 1.62 (17) | C19—C20—C21—C22 | 179.5 (2) |
O7—Zn1—O4—C14 | 89.13 (14) | C19—C20—C21—C25 | −0.4 (4) |
N2—Zn1—O4—C14 | −75.44 (14) | C25—C21—C22—C23 | −2.3 (3) |
C6—C1—C2—O3 | 177.31 (19) | C20—C21—C22—C23 | 177.7 (2) |
C7—C1—C2—O3 | −1.7 (3) | C21—C22—C23—C24 | 0.9 (4) |
C6—C1—C2—C3 | −2.1 (3) | C25—N2—C24—C23 | −0.9 (3) |
C7—C1—C2—C3 | 178.89 (19) | Zn1—N2—C24—C23 | 178.34 (17) |
O3—C2—C3—C4 | −177.8 (2) | C22—C23—C24—N2 | 0.8 (4) |
C1—C2—C3—C4 | 1.7 (3) | C24—N2—C25—C21 | −0.7 (3) |
C2—C3—C4—C5 | −0.2 (4) | Zn1—N2—C25—C21 | 179.95 (16) |
C3—C4—C5—C6 | −0.7 (3) | C24—N2—C25—C26 | −178.95 (18) |
C3—C4—C5—Cl1 | 179.04 (18) | Zn1—N2—C25—C26 | 1.7 (2) |
C4—C5—C6—C1 | 0.3 (3) | C22—C21—C25—N2 | 2.3 (3) |
Cl1—C5—C6—C1 | −179.52 (15) | C20—C21—C25—N2 | −177.8 (2) |
C2—C1—C6—C5 | 1.2 (3) | C22—C21—C25—C26 | −179.5 (2) |
C7—C1—C6—C5 | −179.84 (17) | C20—C21—C25—C26 | 0.5 (3) |
Zn1—O1—C7—O2 | 2.0 (3) | C15—N1—C26—C18 | −1.4 (3) |
Zn1—O1—C7—C1 | −177.15 (13) | Zn1—N1—C26—C18 | −178.73 (17) |
C6—C1—C7—O2 | −170.38 (18) | C15—N1—C26—C25 | 178.12 (19) |
C2—C1—C7—O2 | 8.6 (3) | Zn1—N1—C26—C25 | 0.8 (2) |
C6—C1—C7—O1 | 8.9 (3) | C17—C18—C26—N1 | 1.0 (3) |
C2—C1—C7—O1 | −172.16 (18) | C19—C18—C26—N1 | 180.0 (2) |
C13—C8—C9—O6 | 179.8 (2) | C17—C18—C26—C25 | −178.5 (2) |
C14—C8—C9—O6 | 1.9 (3) | C19—C18—C26—C25 | 0.5 (3) |
C13—C8—C9—C10 | 0.8 (3) | N2—C25—C26—N1 | −1.7 (3) |
C14—C8—C9—C10 | −177.2 (2) | C21—C25—C26—N1 | 179.96 (19) |
O6—C9—C10—C11 | −179.5 (2) | N2—C25—C26—C18 | 177.8 (2) |
C8—C9—C10—C11 | −0.5 (4) | C21—C25—C26—C18 | −0.5 (3) |
C9—C10—C11—C12 | 0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2 | 0.85 (1) | 1.78 (2) | 2.552 (3) | 151 (2) |
O6—H6A···O5 | 0.85 (1) | 1.80 (2) | 2.577 (3) | 150 (2) |
O7—H7A···O4i | 0.85 (1) | 1.97 (1) | 2.785 (3) | 162 (3) |
O7—H7B···O2i | 0.84 (1) | 1.84 (1) | 2.672 (3) | 171 (2) |
Symmetry code: (i) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C7H4ClO3)2(C12H8N2)(H2O)] |
Mr | 606.69 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.681 (4), 11.777 (6), 12.982 (9) |
α, β, γ (°) | 72.06 (2), 76.98 (2), 81.592 (19) |
V (Å3) | 1225.9 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.27 |
Crystal size (mm) | 0.28 × 0.26 × 0.25 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID Weissenberg IP |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12131, 5553, 4462 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.084, 1.04 |
No. of reflections | 5553 |
No. of parameters | 355 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.44 |
Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).
Zn1—O1 | 1.9706 (18) | Zn1—O7 | 2.1154 (17) |
Zn1—O4 | 2.0094 (17) | Zn1—N2 | 2.1599 (18) |
Zn1—N1 | 2.099 (2) | ||
O1—Zn1—O4 | 123.68 (8) | N1—Zn1—O7 | 89.25 (7) |
O1—Zn1—N1 | 98.46 (8) | O1—Zn1—N2 | 96.73 (8) |
O4—Zn1—N1 | 137.84 (7) | O4—Zn1—N2 | 94.37 (7) |
O1—Zn1—O7 | 94.31 (8) | N1—Zn1—N2 | 78.09 (8) |
O4—Zn1—O7 | 88.75 (7) | O7—Zn1—N2 | 164.28 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2 | 0.85 (1) | 1.78 (2) | 2.552 (3) | 151 (2) |
O6—H6A···O5 | 0.85 (1) | 1.80 (2) | 2.577 (3) | 150 (2) |
O7—H7A···O4i | 0.85 (1) | 1.97 (1) | 2.785 (3) | 162 (3) |
O7—H7B···O2i | 0.84 (1) | 1.84 (1) | 2.672 (3) | 171 (2) |
Symmetry code: (i) −x+1, −y+2, −z+2. |
A lot of attention has been paid to the metal salicylate owing to their intriguing structural features (Brownless et al., 1999; Lemoine et al., 2002; Zhu et al., 2003; Yin et al., 2004; Wen et al., 2007a,b,c) and biological applications (Lemoine et al., 2004). We report here the structure of a Zn (II) complex with 5-chloroosalicylate ligand (Melnik et al., 2001). The title complex, Zn(C7H4ClO3)2(C12H8N2)(H2O) was synthesized under hydrothermal conditions. The Zn atom is coordinated in a distorted trigonal bipyramid geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from one 1,10-phenanthroline and one water O atom (Fig. 1). One Zn—N bond is significantly shorter than the other (Zn1—N1 = 2.099 (2) Å, Zn1—N2 = 2.160 (2) Å). These distances are comparable to the Zn—N bond lengths (Zn—N1 = 2.109 (3) Å, Zn—N2 = 2.178 (3) Å) in [Zn(ta)(phen)(H2O)]n (Sun et al., 2001). The complex has rich hydrogen bonds formed by the coordinated water molecule, hydroxy and carboxyl O atoms (Fig. 2). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds interactions (Fig. 3).