


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042316/hy2079sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042316/hy2079Isup2.hkl |
CCDC reference: 663543
A mixture of Zn(NO3)2.6H2O (0.030 g, 0.1 mmol), 2,2'-bipyridine (0.016 g, 0.1 mmol), 5-chlorosalicylic acid (0.035 g, 0.2 mmol) and distilled water (10 ml) was put into a 20 ml Teflon-lined autoclave and then heated at 413 K for 48 h. Yellow block-like crystals of the title compound suitable for X-ray analysis were collected from the reaction mixture.
H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of water molecule and hydroxyl groups were found in a difference Fourier map and refined with a distance restraint of O—H = 0.82 (1)Å and Uiso(H) = 1.2Ueq(O).
Metal salicylate complexes are of current interest owing to their intriguing structural features and biological applications (Brownless et al., 1999; Lemoine, Bendada & Viossat, 2004; Lemoine, Viossat et al., 2004; Wang et al., 2004; Wen et al., 2007a,b). We report here the structure of a zinc(II) complex with 5-chlorosalicylate ligand (Melnik et al., 2001).
The title complex was synthesized under hydrothermal conditions. The ZnII atom is coordinated in a distorted trigonal bipyramidal geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from a 2,2'-bipyridine ligand and one water O atom (Fig. 1 and Table 1). The water molecule, hydroxyl groups and the uncoordinated carboxylate oxygen atoms form intra- and intermolecular O—H···O hydrogen bonds while the 2,2'-bipyridine ligand forms an intermolecular C—H···Cl hydrogen bond with the Cl atom of a 5-chlorosalicylate ligand (Table 2), generating an extended chain architecture along the a axis (Fig. 2). The crystal structure is stabilized by the O—H···O and C—H···Cl hydrogen bonds.
For related literature, see: Brownless et al. (1999); Lemoine, Bendada & Viossat (2004); Lemoine, Viossat et al. (2004); Melnik et al. (2001); Wang et al. (2004); Wen et al. (2007a,b).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Zn(C7H4ClO3)2(C10H8N2)(H2O)] | Z = 2 |
Mr = 582.67 | F(000) = 592 |
Triclinic, P1 | Dx = 1.639 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.114 (5) Å | Cell parameters from 4865 reflections |
b = 11.141 (6) Å | θ = 3.1–26.5° |
c = 11.553 (6) Å | µ = 1.32 mm−1 |
α = 112.72 (2)° | T = 293 K |
β = 93.208 (19)° | Block, yellow |
γ = 97.93 (2)° | 0.52 × 0.50 × 0.47 mm |
V = 1180.8 (11) Å3 |
Rigaku R-AXIS RAPID diffractometer | 4865 independent reflections |
Radiation source: rotation anode | 4269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 26.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.511, Tmax = 0.541 | k = −13→13 |
10689 measured reflections | l = −14→14 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3 |
4865 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 0.28 e Å−3 |
4 restraints | Δρmin = −0.63 e Å−3 |
[Zn(C7H4ClO3)2(C10H8N2)(H2O)] | γ = 97.93 (2)° |
Mr = 582.67 | V = 1180.8 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.114 (5) Å | Mo Kα radiation |
b = 11.141 (6) Å | µ = 1.32 mm−1 |
c = 11.553 (6) Å | T = 293 K |
α = 112.72 (2)° | 0.52 × 0.50 × 0.47 mm |
β = 93.208 (19)° |
Rigaku R-AXIS RAPID diffractometer | 4865 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4269 reflections with I > 2σ(I) |
Tmin = 0.511, Tmax = 0.541 | Rint = 0.023 |
10689 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 4 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.28 e Å−3 |
4865 reflections | Δρmin = −0.63 e Å−3 |
337 parameters |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.93725 (2) | 0.88977 (2) | 0.26799 (2) | 0.03437 (9) | |
N1 | 1.07977 (17) | 0.94611 (18) | 0.15880 (17) | 0.0397 (4) | |
N2 | 0.92448 (17) | 1.08927 (17) | 0.31238 (16) | 0.0377 (4) | |
O1 | 0.84114 (15) | 0.89774 (15) | 0.42384 (14) | 0.0427 (3) | |
O2 | 0.86926 (16) | 0.70100 (16) | 0.41829 (16) | 0.0491 (4) | |
O3 | 0.7135 (2) | 0.58124 (18) | 0.51632 (19) | 0.0605 (5) | |
H3B | 0.781 (2) | 0.599 (3) | 0.486 (3) | 0.073* | |
O4 | 0.78536 (14) | 0.77602 (14) | 0.13849 (13) | 0.0398 (3) | |
O5 | 0.92178 (15) | 0.63737 (17) | 0.04523 (16) | 0.0528 (4) | |
O6 | 0.83933 (18) | 0.4330 (2) | −0.14905 (18) | 0.0645 (5) | |
H6B | 0.889 (3) | 0.489 (3) | −0.088 (2) | 0.077* | |
O7 | 1.06808 (15) | 0.78652 (16) | 0.31565 (14) | 0.0431 (3) | |
H7B | 1.019 (2) | 0.749 (2) | 0.351 (2) | 0.052* | |
H7A | 1.098 (2) | 0.7280 (19) | 0.2633 (18) | 0.052* | |
C1 | 0.70639 (19) | 0.8041 (2) | 0.53918 (18) | 0.0356 (4) | |
C2 | 0.6614 (2) | 0.6930 (2) | 0.5648 (2) | 0.0424 (5) | |
C3 | 0.5595 (3) | 0.6961 (3) | 0.6410 (2) | 0.0548 (6) | |
H3A | 0.5278 | 0.6216 | 0.6560 | 0.066* | |
C4 | 0.5055 (3) | 0.8082 (3) | 0.6941 (2) | 0.0558 (6) | |
H4A | 0.4387 | 0.8105 | 0.7466 | 0.067* | |
C5 | 0.5500 (2) | 0.9180 (2) | 0.6698 (2) | 0.0466 (5) | |
C6 | 0.6491 (2) | 0.9165 (2) | 0.59318 (19) | 0.0404 (4) | |
H6A | 0.6782 | 0.9910 | 0.5773 | 0.049* | |
C7 | 0.81292 (19) | 0.8010 (2) | 0.45482 (18) | 0.0360 (4) | |
C8 | 0.6974 (2) | 0.58857 (19) | −0.04858 (18) | 0.0341 (4) | |
C9 | 0.7182 (2) | 0.4718 (2) | −0.1443 (2) | 0.0428 (5) | |
C10 | 0.6134 (3) | 0.3919 (2) | −0.2364 (2) | 0.0532 (6) | |
H10A | 0.6279 | 0.3143 | −0.3000 | 0.064* | |
C11 | 0.4887 (2) | 0.4273 (2) | −0.2335 (2) | 0.0496 (5) | |
H11A | 0.4180 | 0.3732 | −0.2942 | 0.060* | |
C12 | 0.4687 (2) | 0.5434 (2) | −0.1404 (2) | 0.0398 (5) | |
C13 | 0.5701 (2) | 0.6234 (2) | −0.04767 (18) | 0.0355 (4) | |
H13A | 0.5541 | 0.7005 | 0.0156 | 0.043* | |
C14 | 0.8089 (2) | 0.6724 (2) | 0.05218 (19) | 0.0364 (4) | |
C15 | 1.1575 (2) | 0.8696 (2) | 0.0834 (2) | 0.0483 (5) | |
H15A | 1.1523 | 0.7833 | 0.0771 | 0.058* | |
C16 | 1.2435 (3) | 0.9120 (3) | 0.0157 (2) | 0.0550 (6) | |
H16A | 1.2951 | 0.8554 | −0.0364 | 0.066* | |
C17 | 1.2532 (3) | 1.0403 (3) | 0.0252 (3) | 0.0587 (6) | |
H17A | 1.3111 | 1.0720 | −0.0203 | 0.070* | |
C18 | 1.1753 (3) | 1.1200 (3) | 0.1037 (2) | 0.0540 (6) | |
H18A | 1.1808 | 1.2072 | 0.1126 | 0.065* | |
C19 | 1.0892 (2) | 1.0712 (2) | 0.16902 (19) | 0.0376 (4) | |
C20 | 1.0020 (2) | 1.1516 (2) | 0.25444 (19) | 0.0386 (4) | |
C21 | 0.9986 (3) | 1.2815 (2) | 0.2744 (2) | 0.0517 (6) | |
H21A | 1.0529 | 1.3231 | 0.2336 | 0.062* | |
C22 | 0.9138 (3) | 1.3490 (2) | 0.3554 (3) | 0.0565 (6) | |
H22A | 0.9101 | 1.4364 | 0.3695 | 0.068* | |
C23 | 0.8360 (3) | 1.2871 (3) | 0.4143 (2) | 0.0553 (6) | |
H23A | 0.7785 | 1.3315 | 0.4693 | 0.066* | |
C24 | 0.8430 (2) | 1.1564 (2) | 0.3917 (2) | 0.0471 (5) | |
H24A | 0.7898 | 1.1142 | 0.4326 | 0.057* | |
Cl1 | 0.47871 (7) | 1.05894 (8) | 0.73805 (8) | 0.0718 (2) | |
Cl2 | 0.31025 (6) | 0.58675 (7) | −0.14145 (7) | 0.06070 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03880 (14) | 0.02641 (14) | 0.03341 (14) | 0.00365 (9) | 0.00601 (9) | 0.00750 (10) |
N1 | 0.0443 (9) | 0.0303 (9) | 0.0408 (9) | 0.0028 (7) | 0.0071 (8) | 0.0112 (8) |
N2 | 0.0434 (9) | 0.0299 (9) | 0.0340 (8) | 0.0064 (7) | −0.0002 (7) | 0.0073 (7) |
O1 | 0.0515 (8) | 0.0353 (8) | 0.0426 (8) | 0.0099 (7) | 0.0167 (7) | 0.0146 (7) |
O2 | 0.0550 (9) | 0.0390 (9) | 0.0560 (9) | 0.0161 (7) | 0.0201 (8) | 0.0174 (8) |
O3 | 0.0731 (11) | 0.0379 (9) | 0.0780 (13) | 0.0130 (9) | 0.0271 (10) | 0.0275 (9) |
O4 | 0.0433 (7) | 0.0306 (8) | 0.0355 (7) | 0.0023 (6) | 0.0017 (6) | 0.0041 (6) |
O5 | 0.0399 (8) | 0.0440 (9) | 0.0578 (10) | 0.0066 (7) | 0.0012 (7) | 0.0034 (8) |
O6 | 0.0549 (10) | 0.0540 (12) | 0.0600 (11) | 0.0229 (9) | 0.0037 (8) | −0.0077 (9) |
O7 | 0.0492 (8) | 0.0423 (9) | 0.0363 (8) | 0.0156 (7) | 0.0107 (6) | 0.0106 (7) |
C1 | 0.0369 (9) | 0.0338 (11) | 0.0293 (9) | 0.0018 (8) | 0.0026 (8) | 0.0069 (8) |
C2 | 0.0481 (11) | 0.0356 (12) | 0.0407 (11) | 0.0017 (9) | 0.0040 (9) | 0.0142 (10) |
C3 | 0.0602 (14) | 0.0522 (15) | 0.0551 (14) | −0.0001 (12) | 0.0142 (12) | 0.0269 (13) |
C4 | 0.0524 (13) | 0.0661 (17) | 0.0497 (13) | 0.0079 (12) | 0.0203 (11) | 0.0227 (13) |
C5 | 0.0452 (11) | 0.0474 (13) | 0.0413 (11) | 0.0094 (10) | 0.0110 (9) | 0.0101 (10) |
C6 | 0.0444 (10) | 0.0355 (11) | 0.0377 (10) | 0.0043 (9) | 0.0054 (9) | 0.0114 (9) |
C7 | 0.0387 (9) | 0.0312 (10) | 0.0306 (9) | 0.0034 (8) | 0.0010 (8) | 0.0054 (8) |
C8 | 0.0419 (10) | 0.0263 (10) | 0.0310 (9) | 0.0020 (8) | 0.0050 (8) | 0.0093 (8) |
C9 | 0.0495 (11) | 0.0350 (11) | 0.0381 (11) | 0.0103 (9) | 0.0053 (9) | 0.0073 (9) |
C10 | 0.0682 (15) | 0.0366 (12) | 0.0392 (12) | 0.0078 (11) | 0.0000 (11) | −0.0004 (10) |
C11 | 0.0575 (13) | 0.0400 (13) | 0.0406 (11) | −0.0027 (10) | −0.0085 (10) | 0.0101 (10) |
C12 | 0.0426 (10) | 0.0389 (12) | 0.0409 (11) | 0.0030 (9) | 0.0002 (9) | 0.0212 (10) |
C13 | 0.0468 (10) | 0.0267 (10) | 0.0335 (9) | 0.0056 (8) | 0.0059 (8) | 0.0125 (8) |
C14 | 0.0409 (10) | 0.0293 (10) | 0.0365 (10) | 0.0013 (8) | 0.0037 (8) | 0.0123 (9) |
C15 | 0.0535 (12) | 0.0359 (12) | 0.0534 (13) | 0.0081 (10) | 0.0164 (11) | 0.0142 (11) |
C16 | 0.0569 (13) | 0.0534 (16) | 0.0537 (14) | 0.0105 (12) | 0.0177 (11) | 0.0183 (12) |
C17 | 0.0669 (15) | 0.0567 (16) | 0.0599 (15) | 0.0043 (13) | 0.0217 (13) | 0.0313 (14) |
C18 | 0.0712 (16) | 0.0422 (13) | 0.0548 (14) | 0.0070 (12) | 0.0135 (12) | 0.0260 (12) |
C19 | 0.0429 (10) | 0.0323 (10) | 0.0335 (10) | 0.0011 (8) | −0.0015 (8) | 0.0114 (9) |
C20 | 0.0451 (10) | 0.0309 (10) | 0.0351 (10) | 0.0042 (8) | −0.0050 (8) | 0.0100 (9) |
C21 | 0.0657 (14) | 0.0351 (12) | 0.0545 (13) | 0.0076 (10) | 0.0021 (12) | 0.0193 (11) |
C22 | 0.0676 (15) | 0.0347 (12) | 0.0640 (16) | 0.0169 (11) | −0.0013 (13) | 0.0146 (12) |
C23 | 0.0587 (13) | 0.0440 (14) | 0.0558 (14) | 0.0225 (11) | 0.0017 (12) | 0.0080 (12) |
C24 | 0.0494 (12) | 0.0400 (13) | 0.0459 (12) | 0.0118 (10) | 0.0050 (10) | 0.0095 (10) |
Cl1 | 0.0735 (4) | 0.0640 (4) | 0.0754 (5) | 0.0299 (4) | 0.0333 (4) | 0.0159 (4) |
Cl2 | 0.0481 (3) | 0.0614 (4) | 0.0732 (4) | 0.0105 (3) | −0.0080 (3) | 0.0291 (3) |
Zn1—O4 | 1.9863 (17) | C6—H6A | 0.9300 |
Zn1—O7 | 2.0507 (17) | C8—C13 | 1.394 (3) |
Zn1—O1 | 2.0715 (17) | C8—C9 | 1.396 (3) |
Zn1—N2 | 2.104 (2) | C8—C14 | 1.490 (3) |
Zn1—N1 | 2.1514 (19) | C9—C10 | 1.389 (3) |
N1—C15 | 1.339 (3) | C10—C11 | 1.371 (4) |
N1—C19 | 1.342 (3) | C10—H10A | 0.9300 |
N2—C24 | 1.342 (3) | C11—C12 | 1.376 (3) |
N2—C20 | 1.346 (3) | C11—H11A | 0.9300 |
O1—C7 | 1.263 (3) | C12—C13 | 1.371 (3) |
O2—C7 | 1.258 (2) | C12—Cl2 | 1.736 (2) |
O3—C2 | 1.348 (3) | C13—H13A | 0.9300 |
O3—H3B | 0.82 (3) | C15—C16 | 1.356 (3) |
O4—C14 | 1.264 (3) | C15—H15A | 0.9300 |
O5—C14 | 1.254 (2) | C16—C17 | 1.380 (4) |
O6—C9 | 1.351 (3) | C16—H16A | 0.9300 |
O6—H6B | 0.82 (3) | C17—C18 | 1.372 (4) |
O7—H7B | 0.826 (10) | C17—H17A | 0.9300 |
O7—H7A | 0.810 (10) | C18—C19 | 1.372 (3) |
C1—C6 | 1.389 (3) | C18—H18A | 0.9300 |
C1—C2 | 1.403 (3) | C19—C20 | 1.479 (3) |
C1—C7 | 1.488 (3) | C20—C21 | 1.380 (3) |
C2—C3 | 1.389 (3) | C21—C22 | 1.379 (4) |
C3—C4 | 1.367 (4) | C21—H21A | 0.9300 |
C3—H3A | 0.9300 | C22—C23 | 1.352 (4) |
C4—C5 | 1.380 (4) | C22—H22A | 0.9300 |
C4—H4A | 0.9300 | C23—C24 | 1.389 (3) |
C5—C6 | 1.372 (3) | C23—H23A | 0.9300 |
C5—Cl1 | 1.740 (2) | C24—H24A | 0.9300 |
O4—Zn1—O7 | 113.87 (7) | O6—C9—C8 | 121.2 (2) |
O4—Zn1—O1 | 96.40 (7) | C10—C9—C8 | 120.3 (2) |
O7—Zn1—O1 | 88.52 (7) | C11—C10—C9 | 120.0 (2) |
O4—Zn1—N2 | 109.12 (7) | C11—C10—H10A | 120.0 |
O7—Zn1—N2 | 136.91 (7) | C9—C10—H10A | 120.0 |
O1—Zn1—N2 | 89.69 (7) | C10—C11—C12 | 119.7 (2) |
O4—Zn1—N1 | 103.25 (8) | C10—C11—H11A | 120.2 |
O7—Zn1—N1 | 90.52 (7) | C12—C11—H11A | 120.2 |
O1—Zn1—N1 | 158.89 (7) | C13—C12—C11 | 121.4 (2) |
N2—Zn1—N1 | 76.73 (7) | C13—C12—Cl2 | 120.20 (17) |
C15—N1—C19 | 118.18 (19) | C11—C12—Cl2 | 118.42 (17) |
C15—N1—Zn1 | 126.70 (15) | C12—C13—C8 | 119.75 (19) |
C19—N1—Zn1 | 115.13 (14) | C12—C13—H13A | 120.1 |
C24—N2—C20 | 118.58 (19) | C8—C13—H13A | 120.1 |
C24—N2—Zn1 | 124.50 (16) | O5—C14—O4 | 123.54 (19) |
C20—N2—Zn1 | 116.90 (14) | O5—C14—C8 | 118.04 (18) |
C7—O1—Zn1 | 124.19 (13) | O4—C14—C8 | 118.40 (17) |
C2—O3—H3B | 106 (2) | N1—C15—C16 | 123.1 (2) |
C14—O4—Zn1 | 117.68 (13) | N1—C15—H15A | 118.4 |
C9—O6—H6B | 106 (2) | C16—C15—H15A | 118.4 |
Zn1—O7—H7B | 100.3 (17) | C15—C16—C17 | 119.0 (2) |
Zn1—O7—H7A | 122.6 (18) | C15—C16—H16A | 120.5 |
H7B—O7—H7A | 105 (3) | C17—C16—H16A | 120.5 |
C6—C1—C2 | 118.89 (19) | C18—C17—C16 | 118.3 (2) |
C6—C1—C7 | 120.63 (19) | C18—C17—H17A | 120.9 |
C2—C1—C7 | 120.48 (19) | C16—C17—H17A | 120.9 |
O3—C2—C3 | 118.2 (2) | C19—C18—C17 | 120.1 (2) |
O3—C2—C1 | 121.9 (2) | C19—C18—H18A | 120.0 |
C3—C2—C1 | 119.9 (2) | C17—C18—H18A | 120.0 |
C4—C3—C2 | 120.2 (2) | N1—C19—C18 | 121.3 (2) |
C4—C3—H3A | 119.9 | N1—C19—C20 | 115.92 (18) |
C2—C3—H3A | 119.9 | C18—C19—C20 | 122.8 (2) |
C3—C4—C5 | 120.1 (2) | N2—C20—C21 | 121.5 (2) |
C3—C4—H4A | 119.9 | N2—C20—C19 | 115.30 (18) |
C5—C4—H4A | 119.9 | C21—C20—C19 | 123.2 (2) |
C6—C5—C4 | 120.6 (2) | C22—C21—C20 | 119.3 (2) |
C6—C5—Cl1 | 120.34 (19) | C22—C21—H21A | 120.4 |
C4—C5—Cl1 | 119.05 (18) | C20—C21—H21A | 120.4 |
C5—C6—C1 | 120.3 (2) | C23—C22—C21 | 119.5 (2) |
C5—C6—H6A | 119.9 | C23—C22—H22A | 120.2 |
C1—C6—H6A | 119.9 | C21—C22—H22A | 120.2 |
O2—C7—O1 | 123.97 (19) | C22—C23—C24 | 119.2 (2) |
O2—C7—C1 | 117.45 (19) | C22—C23—H23A | 120.4 |
O1—C7—C1 | 118.57 (18) | C24—C23—H23A | 120.4 |
C13—C8—C9 | 118.82 (19) | N2—C24—C23 | 121.9 (2) |
C13—C8—C14 | 120.88 (18) | N2—C24—H24A | 119.1 |
C9—C8—C14 | 120.28 (18) | C23—C24—H24A | 119.1 |
O6—C9—C10 | 118.4 (2) | ||
O4—Zn1—N1—C15 | −74.08 (19) | C14—C8—C9—O6 | −0.9 (3) |
O7—Zn1—N1—C15 | 40.62 (19) | C13—C8—C9—C10 | −0.3 (3) |
O1—Zn1—N1—C15 | 127.8 (2) | C14—C8—C9—C10 | 178.3 (2) |
N2—Zn1—N1—C15 | 179.06 (19) | O6—C9—C10—C11 | 179.2 (2) |
O4—Zn1—N1—C19 | 105.74 (15) | C8—C9—C10—C11 | −0.1 (4) |
O7—Zn1—N1—C19 | −139.56 (15) | C9—C10—C11—C12 | 1.1 (4) |
O1—Zn1—N1—C19 | −52.3 (2) | C10—C11—C12—C13 | −1.8 (4) |
N2—Zn1—N1—C19 | −1.13 (14) | C10—C11—C12—Cl2 | 178.80 (19) |
O4—Zn1—N2—C24 | 80.39 (18) | C11—C12—C13—C8 | 1.4 (3) |
O7—Zn1—N2—C24 | −103.76 (18) | Cl2—C12—C13—C8 | −179.18 (15) |
O1—Zn1—N2—C24 | −16.27 (17) | C9—C8—C13—C12 | −0.4 (3) |
N1—Zn1—N2—C24 | −179.96 (18) | C14—C8—C13—C12 | −178.97 (18) |
O4—Zn1—N2—C20 | −98.18 (15) | Zn1—O4—C14—O5 | 0.9 (3) |
O7—Zn1—N2—C20 | 77.67 (17) | Zn1—O4—C14—C8 | −177.68 (13) |
O1—Zn1—N2—C20 | 165.16 (14) | C13—C8—C14—O5 | −178.77 (19) |
N1—Zn1—N2—C20 | 1.47 (14) | C9—C8—C14—O5 | 2.7 (3) |
O4—Zn1—O1—C7 | 69.96 (17) | C13—C8—C14—O4 | −0.1 (3) |
O7—Zn1—O1—C7 | −43.90 (17) | C9—C8—C14—O4 | −178.68 (19) |
N2—Zn1—O1—C7 | 179.16 (16) | C19—N1—C15—C16 | −1.0 (3) |
N1—Zn1—O1—C7 | −131.49 (19) | Zn1—N1—C15—C16 | 178.78 (19) |
O7—Zn1—O4—C14 | −35.97 (16) | N1—C15—C16—C17 | 0.7 (4) |
O1—Zn1—O4—C14 | −127.18 (15) | C15—C16—C17—C18 | 0.2 (4) |
N2—Zn1—O4—C14 | 140.92 (14) | C16—C17—C18—C19 | −0.8 (4) |
N1—Zn1—O4—C14 | 60.59 (16) | C15—N1—C19—C18 | 0.4 (3) |
C6—C1—C2—O3 | −179.4 (2) | Zn1—N1—C19—C18 | −179.41 (17) |
C7—C1—C2—O3 | 1.0 (3) | C15—N1—C19—C20 | −179.48 (18) |
C6—C1—C2—C3 | 1.3 (3) | Zn1—N1—C19—C20 | 0.7 (2) |
C7—C1—C2—C3 | −178.3 (2) | C17—C18—C19—N1 | 0.5 (4) |
O3—C2—C3—C4 | 178.8 (2) | C17—C18—C19—C20 | −179.6 (2) |
C1—C2—C3—C4 | −1.9 (4) | C24—N2—C20—C21 | −0.4 (3) |
C2—C3—C4—C5 | 1.5 (4) | Zn1—N2—C20—C21 | 178.29 (16) |
C3—C4—C5—C6 | −0.4 (4) | C24—N2—C20—C19 | 179.77 (18) |
C3—C4—C5—Cl1 | 179.7 (2) | Zn1—N2—C20—C19 | −1.6 (2) |
C4—C5—C6—C1 | −0.2 (3) | N1—C19—C20—N2 | 0.6 (3) |
Cl1—C5—C6—C1 | 179.72 (16) | C18—C19—C20—N2 | −179.3 (2) |
C2—C1—C6—C5 | −0.2 (3) | N1—C19—C20—C21 | −179.3 (2) |
C7—C1—C6—C5 | 179.32 (19) | C18—C19—C20—C21 | 0.8 (3) |
Zn1—O1—C7—O2 | 20.1 (3) | N2—C20—C21—C22 | −0.1 (3) |
Zn1—O1—C7—C1 | −159.64 (13) | C19—C20—C21—C22 | 179.8 (2) |
C6—C1—C7—O2 | 173.64 (19) | C20—C21—C22—C23 | 0.3 (4) |
C2—C1—C7—O2 | −6.8 (3) | C21—C22—C23—C24 | −0.1 (4) |
C6—C1—C7—O1 | −6.6 (3) | C20—N2—C24—C23 | 0.6 (3) |
C2—C1—C7—O1 | 172.97 (19) | Zn1—N2—C24—C23 | −177.97 (17) |
C13—C8—C9—O6 | −179.5 (2) | C22—C23—C24—N2 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7B···O2 | 0.82 (1) | 1.85 (1) | 2.640 (2) | 160 (2) |
O7—H7A···O6i | 0.82 (1) | 1.98 (1) | 2.786 (3) | 171 (2) |
O3—H3B···O2 | 0.82 (3) | 1.78 (2) | 2.516 (3) | 148 (3) |
O6—H6B···O5 | 0.82 (3) | 1.74 (2) | 2.498 (3) | 152 (2) |
C16—H16A···Cl2ii | 0.93 | 2.79 | 3.552 (3) | 140 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C7H4ClO3)2(C10H8N2)(H2O)] |
Mr | 582.67 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.114 (5), 11.141 (6), 11.553 (6) |
α, β, γ (°) | 112.72 (2), 93.208 (19), 97.93 (2) |
V (Å3) | 1180.8 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.32 |
Crystal size (mm) | 0.52 × 0.50 × 0.47 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.511, 0.541 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10689, 4865, 4269 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.094, 1.11 |
No. of reflections | 4865 |
No. of parameters | 337 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.63 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Zn1—O4 | 1.9863 (17) | Zn1—N2 | 2.104 (2) |
Zn1—O7 | 2.0507 (17) | Zn1—N1 | 2.1514 (19) |
Zn1—O1 | 2.0715 (17) | ||
O4—Zn1—O7 | 113.87 (7) | O1—Zn1—N2 | 89.69 (7) |
O4—Zn1—O1 | 96.40 (7) | O4—Zn1—N1 | 103.25 (8) |
O7—Zn1—O1 | 88.52 (7) | O7—Zn1—N1 | 90.52 (7) |
O4—Zn1—N2 | 109.12 (7) | O1—Zn1—N1 | 158.89 (7) |
O7—Zn1—N2 | 136.91 (7) | N2—Zn1—N1 | 76.73 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7B···O2 | 0.82 (1) | 1.85 (1) | 2.640 (2) | 160 (2) |
O7—H7A···O6i | 0.82 (1) | 1.98 (1) | 2.786 (3) | 171 (2) |
O3—H3B···O2 | 0.82 (3) | 1.78 (2) | 2.516 (3) | 148 (3) |
O6—H6B···O5 | 0.82 (3) | 1.74 (2) | 2.498 (3) | 152 (2) |
C16—H16A···Cl2ii | 0.93 | 2.792 | 3.552 (3) | 140 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z. |
Metal salicylate complexes are of current interest owing to their intriguing structural features and biological applications (Brownless et al., 1999; Lemoine, Bendada & Viossat, 2004; Lemoine, Viossat et al., 2004; Wang et al., 2004; Wen et al., 2007a,b). We report here the structure of a zinc(II) complex with 5-chlorosalicylate ligand (Melnik et al., 2001).
The title complex was synthesized under hydrothermal conditions. The ZnII atom is coordinated in a distorted trigonal bipyramidal geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from a 2,2'-bipyridine ligand and one water O atom (Fig. 1 and Table 1). The water molecule, hydroxyl groups and the uncoordinated carboxylate oxygen atoms form intra- and intermolecular O—H···O hydrogen bonds while the 2,2'-bipyridine ligand forms an intermolecular C—H···Cl hydrogen bond with the Cl atom of a 5-chlorosalicylate ligand (Table 2), generating an extended chain architecture along the a axis (Fig. 2). The crystal structure is stabilized by the O—H···O and C—H···Cl hydrogen bonds.