In the crystal, the title centrosymmetric ZnII complex molecules are linked by O—H⋯O hydrogen bonds into supramolecular chains propagating along the [110] direction.
Keywords: crystal structure, zinc complex, benzoate, nicotinamide derivatives
Abstract
In the title complex, [Zn(C8H4NO2)2(C10H14N2O)2(H2O)2], the ZnII cation, located on an inversion centre, is coordinated by two water molecules, two 4-cyanobenzoate (CB) anions and two diethylnicotinamide (DENA) ligands in a distorted N2O4 octahedral geometry. In the molecule, the dihedral angle between the planar carboxylate group and the adjacent benzene ring is 9.50 (14)°, while the benzene and pyridine rings are oriented at a dihedral angle of 56.99 (5)°. The water molecules exhibit both an intramolecular hydrogen bond [to the non-coordinating carboxylate O atom, enclosing an S(6) hydrogen-bonding motif, where O⋯O = 2.6419 (19) Å] and an intermolecular hydrogen bond [to the amide carbonyl O atom, enclosing an R 2 2(16) ring motif, where O⋯O = 2.827 (2) Å]; the latter lead to the formation of supramolecular chains propagating along the [110] direction.
Chemical context
Nicotinamide (NA) is one form of niacin. A deficiency of this vitamin leads to loss of copper from the body, known as pellagra disease. Victims of pellagra show unusually high serum and urinary copper levels (Krishnamachari, 1974 ▸). The nicotinic acid derivative N,N-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972 ▸). The structures of some complexes obtained from the reactions of transition metal(II) ions with NA and DENA as ligands, e.g. [Ni(NA)2(C7H4ClO2)2(H2O)2] (Hökelek et al., 2009a
▸) and [Ni(C7H4ClO2)2(C10H14N2O)2(H2O)2] (Hökelek et al., 2009b
▸), have been the subject of much interest in our laboratory.
The structure-function–coordination relationships of the arylcarboxylate ion in ZnII complexes of benzoic acid derivatives may change depending on the nature and position of the substituted groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the pH and temperature of synthesis (Shnulin et al., 1981 ▸; Nadzhafov et al., 1981 ▸; Antsyshkina et al., 1980 ▸; Adiwidjaja et al., 1978 ▸). When pyridine and its derivatives are used instead of water molecules, the structure is completely different (Catterick et al., 1974 ▸). In this context, we synthesized a ZnII-containing compound with 4-cyanobenzoate (CB) and DENA ligands, namely trans-diaquabis(4-cyanobenzoato-κO)bis(N,N-diethylnicotinamide-κN)zinc(II), [Zn(DENA)2(CB)2(H2O)2], and report herein its crystal structure.
Structural commentary
The asymmetric unit of the crystal structure of the title complex contains one ZnII atom located on an inversion centre, one 4-cyanobenzoate (CB) ligand, one N,N-diethylnicotinamide (DENA) ligand and one water molecule, all ligands coordinating to the ZnII atom in a monodentate manner (Fig. 1 ▸).
Figure 1.
The molecular structure of the title complex, showing the atom-numbering scheme for the asymmetric unit. Unlabelled atoms are generated by the symmetry operation −x, −y, −z. Displacement ellipsoids are drawn at the 40% probability level. Intramolecular O—Hw⋯Oc (w = water and c = non-coordinating carboxylate O atom) hydrogen bonds, enclosing S(6) hydrogen-bonding motifs, are shown as dashed lines.
The two carboxylate O atoms (O2 and O2i) of the two symmetry-related monodentate CB anions and the two symmetry-related water O atoms (O4 and O4i) around the Zn1 atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination sphere is completed by the two pyridine N atoms (N2 and N2i) of the two symmetry-related monodentate DENA ligands in the axial positions [symmetry code: (i) −x, −y, −z] (Fig. 1 ▸).
In the carboxylate groups, the C—O bonds for coordinating O atoms are 0.0148 (19) Å longer than those of the non-coordinating ones [C1—O1 = 1.2436 (19) Å and C1—O2 = 1.2584 (18) Å], indicating delocalized bonding arrangements rather than localized single and double bonds. The Zn—O bond lengths are 2.1503 (11) Å (for water O atoms) and 2.0842 (10) Å (for benzoate O atoms) and the Zn—N bond length is 2.1501 (11) Å, the Zn—O bond lengths for water oxygen atoms are ca 0.07 Å longer than those involving the benzoate oxygen atoms. The Zn1 atom lies 0.7093 (1) Å below the planar (O1/O2/C1) carboxylate group. The O—Zn—O and O–Zn—N bond angles range from 87.64 (5) to 92.36 (5)°.
The dihedral angle between the planar carboxylate group (O1/O2/C1) and the adjacent benzene ring (C2–C7) is 9.50 (14)°, while the benzene and pyridine (N2/C9–C14) rings are oriented at a dihedral angle of 56.99 (5)°.
Supramolecular features
Intramolecular O—Hw⋯Oc (w = water, c = non-coordinating carboxylate O atom) hydrogen bonds (Table 1 ▸) link two of the water ligands to the CB anions, enclosing S(6) hydrogen-bonding motifs (Fig. 1 ▸). The other water H atom is involved in intermolecular O—Hw⋯ODENA (ODENA = carbonyl O atom of N,N-diethylnicotinamide) hydrogen bonds (Table 1 ▸), enclosing 
(16) ring motifs and leading to the formation of infinite chains (Fig. 2 ▸) propagating along the [110] direction (Fig. 3 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O4—H41⋯O1i | 0.83 (2) | 1.84 (2) | 2.6419 (19) | 161 (2) |
| O4—H42⋯O3ii | 0.82 (2) | 2.03 (2) | 2.827 (2) | 163 (2) |
Symmetry codes: (i) 
; (ii) 
.
Figure 2.
Part of the supramolecular chain of the title compound. Intermolecular O—Hw⋯ODENA (ODENA = carbonyl O atom of N,N-diethylnicotinamide) hydrogen bonds, enclosing (16) ring motifs, are shown as dashed lines. The non-bonding H atoms have been omitted for clarity.
Figure 3.
Part of the crystal structure. Intra- and intermolecular (O—Hw⋯Oc and O—Hw⋯ODENA, respectively) hydrogen bonds are shown as dashed lines (see Table 1 ▸). The non-bonding H atoms have been omitted for clarity.
Synthesis and crystallization
The title compound was prepared by the reaction of ZnSO4·7H2O (1.44 g, 5 mmol) in H2O (50 ml) and diethylnicotinamide (1.78 g, 10 mmol) in H2O (10 ml) with sodium 4-cyanobenzoate (1.69 g, 10 mmol) in H2O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving translucent intense colourless single crystals.
Refinement
The experimental details including the crystal data, data collection and refinement are summarized in Table 2 ▸. Atoms H41 and H42 (for H2O) were located in a difference Fourier map and were refined freely. The C-bound H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with U iso(H) = k × U eq(C), where k = 1.5 for methyl H atoms and k = 1.2 for aromatic and methylene H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [Zn(C8H4NO2)2(C10H14N2O)2(H2O)2] |
| M r | 750.13 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 296 |
| a, b, c (Å) | 7.4916 (3), 8.5915 (3), 15.0343 (6) |
| α, β, γ (°) | 86.363 (3), 75.894 (2), 74.390 (2) |
| V (Å3) | 903.87 (6) |
| Z | 1 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.74 |
| Crystal size (mm) | 0.45 × 0.30 × 0.24 |
| Data collection | |
| Diffractometer | Bruker SMART BREEZE CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) |
| T min, T max | 0.74, 0.84 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 19149, 4366, 4029 |
| R int | 0.020 |
| (sin θ/λ)max (Å−1) | 0.666 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.032, 0.084, 1.06 |
| No. of reflections | 4366 |
| No. of parameters | 242 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.56, −0.23 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016013815/xu5890sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016013815/xu5890Isup2.hkl
CCDC reference: 1501337
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Aksaray University Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). This work was supported financially by the Kafkas University, Scientific Research Projects Coordinator (project No. 2016-FM-49).
supplementary crystallographic information
Crystal data
| [Zn(C8H4NO2)2(C10H14N2O)2(H2O)2] | Z = 1 |
| Mr = 750.13 | F(000) = 392 |
| Triclinic, P1 | Dx = 1.378 Mg m−3 |
| a = 7.4916 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.5915 (3) Å | Cell parameters from 9994 reflections |
| c = 15.0343 (6) Å | θ = 2.8–28.2° |
| α = 86.363 (3)° | µ = 0.74 mm−1 |
| β = 75.894 (2)° | T = 296 K |
| γ = 74.390 (2)° | Prism, translucent intense colourless |
| V = 903.87 (6) Å3 | 0.45 × 0.30 × 0.24 mm |
Data collection
| Bruker SMART BREEZE CCD diffractometer | 4366 independent reflections |
| Radiation source: fine-focus sealed tube | 4029 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.020 |
| φ and ω scans | θmax = 28.3°, θmin = 1.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −9→9 |
| Tmin = 0.74, Tmax = 0.84 | k = −11→11 |
| 19149 measured reflections | l = −19→19 |
Refinement
| 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0458P)2 + 0.2769P] where P = (Fo2 + 2Fc2)/3 |
| 4366 reflections | (Δ/σ)max < 0.001 |
| 242 parameters | Δρmax = 0.56 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.0000 | 0.0000 | 0.0000 | 0.02730 (8) | |
| O1 | 0.10666 (18) | 0.0679 (2) | −0.22778 (9) | 0.0585 (4) | |
| O2 | 0.23197 (15) | 0.01976 (13) | −0.10544 (7) | 0.0340 (2) | |
| O3 | 0.51295 (19) | −0.62718 (18) | −0.11834 (9) | 0.0571 (4) | |
| O4 | 0.19075 (17) | −0.10842 (16) | 0.08623 (9) | 0.0414 (3) | |
| H41 | 0.115 (3) | −0.110 (3) | 0.1366 (17) | 0.056 (7)* | |
| H42 | 0.277 (3) | −0.191 (3) | 0.0848 (16) | 0.059 (7)* | |
| N1 | 1.1465 (3) | −0.2028 (3) | −0.46622 (14) | 0.0755 (6) | |
| N2 | 0.02013 (16) | −0.22996 (14) | −0.05596 (8) | 0.0288 (2) | |
| N3 | 0.4843 (2) | −0.58488 (17) | −0.26504 (9) | 0.0402 (3) | |
| C1 | 0.2428 (2) | 0.02304 (18) | −0.19037 (10) | 0.0324 (3) | |
| C2 | 0.4408 (2) | −0.03327 (17) | −0.25173 (10) | 0.0304 (3) | |
| C3 | 0.4653 (2) | −0.0552 (2) | −0.34513 (11) | 0.0423 (4) | |
| H3 | 0.3593 | −0.0388 | −0.3698 | 0.051* | |
| C4 | 0.6461 (3) | −0.1012 (2) | −0.40159 (11) | 0.0466 (4) | |
| H4 | 0.6621 | −0.1157 | −0.4641 | 0.056* | |
| C5 | 0.8044 (2) | −0.12572 (19) | −0.36423 (11) | 0.0383 (3) | |
| C6 | 0.7815 (2) | −0.1071 (2) | −0.27117 (12) | 0.0415 (4) | |
| H6 | 0.8876 | −0.1252 | −0.2463 | 0.050* | |
| C7 | 0.5995 (2) | −0.0614 (2) | −0.21525 (11) | 0.0368 (3) | |
| H7 | 0.5836 | −0.0493 | −0.1525 | 0.044* | |
| C8 | 0.9951 (3) | −0.1689 (2) | −0.42235 (13) | 0.0507 (4) | |
| C9 | −0.1333 (2) | −0.28196 (18) | −0.05414 (10) | 0.0323 (3) | |
| H9 | −0.2528 | −0.2183 | −0.0253 | 0.039* | |
| C10 | −0.1218 (2) | −0.4269 (2) | −0.09346 (12) | 0.0379 (3) | |
| H10 | −0.2314 | −0.4600 | −0.0909 | 0.045* | |
| C11 | 0.0555 (2) | −0.52178 (18) | −0.13656 (11) | 0.0386 (3) | |
| H11 | 0.0669 | −0.6187 | −0.1644 | 0.046* | |
| C12 | 0.2158 (2) | −0.47000 (17) | −0.13758 (10) | 0.0317 (3) | |
| C13 | 0.1916 (2) | −0.32445 (17) | −0.09573 (10) | 0.0302 (3) | |
| H13 | 0.2994 | −0.2907 | −0.0952 | 0.036* | |
| C14 | 0.4178 (2) | −0.56899 (17) | −0.17441 (11) | 0.0354 (3) | |
| C15 | 0.3800 (3) | −0.5002 (2) | −0.33283 (12) | 0.0488 (4) | |
| H15A | 0.4514 | −0.4299 | −0.3693 | 0.059* | |
| H15B | 0.2577 | −0.4329 | −0.3008 | 0.059* | |
| C16 | 0.3474 (3) | −0.6144 (3) | −0.39581 (16) | 0.0663 (6) | |
| H16A | 0.2720 | −0.5537 | −0.4359 | 0.099* | |
| H16B | 0.2815 | −0.6874 | −0.3600 | 0.099* | |
| H16C | 0.4680 | −0.6748 | −0.4317 | 0.099* | |
| C17 | 0.6830 (3) | −0.6752 (2) | −0.30132 (13) | 0.0481 (4) | |
| H17A | 0.6893 | −0.7410 | −0.3527 | 0.058* | |
| H17B | 0.7267 | −0.7473 | −0.2542 | 0.058* | |
| C18 | 0.8137 (4) | −0.5660 (4) | −0.3324 (2) | 0.0831 (8) | |
| H18A | 0.9426 | −0.6304 | −0.3527 | 0.125* | |
| H18B | 0.8053 | −0.4984 | −0.2823 | 0.125* | |
| H18C | 0.7766 | −0.4997 | −0.3821 | 0.125* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.02409 (12) | 0.02632 (12) | 0.02797 (13) | −0.00158 (8) | −0.00370 (8) | −0.00585 (8) |
| O1 | 0.0317 (6) | 0.0954 (11) | 0.0390 (7) | −0.0015 (6) | −0.0080 (5) | 0.0024 (7) |
| O2 | 0.0289 (5) | 0.0415 (6) | 0.0297 (5) | −0.0098 (4) | −0.0014 (4) | −0.0061 (4) |
| O3 | 0.0501 (7) | 0.0621 (8) | 0.0419 (7) | 0.0212 (6) | −0.0165 (6) | −0.0093 (6) |
| O4 | 0.0310 (6) | 0.0488 (7) | 0.0375 (6) | 0.0048 (5) | −0.0113 (5) | −0.0020 (5) |
| N1 | 0.0492 (10) | 0.0958 (16) | 0.0549 (11) | 0.0045 (10) | 0.0111 (9) | −0.0003 (10) |
| N2 | 0.0268 (6) | 0.0263 (5) | 0.0297 (6) | −0.0019 (4) | −0.0049 (5) | −0.0032 (4) |
| N3 | 0.0392 (7) | 0.0349 (7) | 0.0353 (7) | 0.0061 (5) | −0.0050 (6) | −0.0021 (5) |
| C1 | 0.0295 (7) | 0.0314 (7) | 0.0343 (7) | −0.0074 (5) | −0.0040 (6) | −0.0017 (6) |
| C2 | 0.0314 (7) | 0.0303 (7) | 0.0284 (7) | −0.0094 (5) | −0.0033 (6) | −0.0001 (5) |
| C3 | 0.0372 (8) | 0.0564 (10) | 0.0321 (8) | −0.0091 (7) | −0.0094 (6) | −0.0015 (7) |
| C4 | 0.0471 (10) | 0.0597 (11) | 0.0266 (7) | −0.0070 (8) | −0.0034 (7) | −0.0035 (7) |
| C5 | 0.0343 (8) | 0.0374 (8) | 0.0349 (8) | −0.0048 (6) | 0.0025 (6) | −0.0014 (6) |
| C6 | 0.0318 (8) | 0.0527 (10) | 0.0379 (8) | −0.0086 (7) | −0.0059 (6) | −0.0035 (7) |
| C7 | 0.0334 (8) | 0.0469 (9) | 0.0287 (7) | −0.0099 (6) | −0.0040 (6) | −0.0046 (6) |
| C8 | 0.0421 (10) | 0.0553 (11) | 0.0406 (9) | −0.0013 (8) | 0.0036 (8) | 0.0016 (8) |
| C9 | 0.0281 (7) | 0.0340 (7) | 0.0323 (7) | −0.0042 (5) | −0.0067 (6) | −0.0002 (6) |
| C10 | 0.0364 (8) | 0.0381 (8) | 0.0436 (9) | −0.0124 (6) | −0.0148 (7) | 0.0002 (7) |
| C11 | 0.0466 (9) | 0.0285 (7) | 0.0422 (8) | −0.0065 (6) | −0.0158 (7) | −0.0061 (6) |
| C12 | 0.0349 (7) | 0.0258 (6) | 0.0296 (7) | 0.0007 (5) | −0.0077 (6) | −0.0015 (5) |
| C13 | 0.0276 (7) | 0.0275 (6) | 0.0323 (7) | −0.0032 (5) | −0.0052 (5) | −0.0024 (5) |
| C14 | 0.0373 (8) | 0.0257 (6) | 0.0367 (8) | 0.0032 (6) | −0.0080 (6) | −0.0054 (6) |
| C15 | 0.0511 (10) | 0.0477 (10) | 0.0367 (9) | 0.0030 (8) | −0.0089 (8) | 0.0050 (7) |
| C16 | 0.0596 (13) | 0.0810 (16) | 0.0555 (12) | −0.0073 (11) | −0.0190 (10) | −0.0058 (11) |
| C17 | 0.0395 (9) | 0.0476 (9) | 0.0434 (9) | 0.0054 (7) | −0.0015 (7) | −0.0057 (8) |
| C18 | 0.0576 (14) | 0.099 (2) | 0.093 (2) | −0.0287 (14) | −0.0102 (13) | 0.0008 (16) |
Geometric parameters (Å, º)
| Zn1—O2 | 2.0842 (10) | C6—H6 | 0.9300 |
| Zn1—O2i | 2.0842 (10) | C7—C6 | 1.384 (2) |
| Zn1—O4 | 2.1503 (11) | C7—H7 | 0.9300 |
| Zn1—O4i | 2.1503 (11) | C8—N1 | 1.135 (3) |
| Zn1—N2 | 2.1501 (11) | C9—C10 | 1.385 (2) |
| Zn1—N2i | 2.1501 (11) | C9—H9 | 0.9300 |
| O1—C1 | 1.2436 (19) | C10—H10 | 0.9300 |
| O2—C1 | 1.2584 (18) | C11—C10 | 1.383 (2) |
| O3—C14 | 1.231 (2) | C11—H11 | 0.9300 |
| O4—H41 | 0.83 (2) | C12—C11 | 1.385 (2) |
| O4—H42 | 0.82 (2) | C12—C14 | 1.509 (2) |
| N2—C9 | 1.3348 (19) | C13—C12 | 1.384 (2) |
| N2—C13 | 1.3389 (17) | C13—H13 | 0.9300 |
| N3—C14 | 1.334 (2) | C15—C16 | 1.510 (3) |
| N3—C15 | 1.472 (2) | C15—H15A | 0.9700 |
| N3—C17 | 1.467 (2) | C15—H15B | 0.9700 |
| C1—C2 | 1.513 (2) | C16—H16A | 0.9600 |
| C2—C3 | 1.389 (2) | C16—H16B | 0.9600 |
| C2—C7 | 1.386 (2) | C16—H16C | 0.9600 |
| C3—C4 | 1.380 (2) | C17—C18 | 1.508 (3) |
| C3—H3 | 0.9300 | C17—H17A | 0.9700 |
| C4—H4 | 0.9300 | C17—H17B | 0.9700 |
| C5—C4 | 1.393 (2) | C18—H18A | 0.9600 |
| C5—C6 | 1.382 (2) | C18—H18B | 0.9600 |
| C5—C8 | 1.446 (2) | C18—H18C | 0.9600 |
| O2—Zn1—O2i | 180.00 (7) | C6—C7—H7 | 119.7 |
| O2—Zn1—O4 | 89.94 (5) | N1—C8—C5 | 178.4 (2) |
| O2i—Zn1—O4 | 90.06 (5) | N2—C9—C10 | 122.61 (14) |
| O2—Zn1—O4i | 90.06 (5) | N2—C9—H9 | 118.7 |
| O2i—Zn1—O4i | 89.94 (5) | C10—C9—H9 | 118.7 |
| O2—Zn1—N2 | 88.48 (4) | C9—C10—H10 | 120.6 |
| O2i—Zn1—N2 | 91.52 (4) | C11—C10—C9 | 118.88 (14) |
| O2—Zn1—N2i | 91.52 (4) | C11—C10—H10 | 120.6 |
| O2i—Zn1—N2i | 88.48 (4) | C10—C11—C12 | 118.92 (14) |
| O4i—Zn1—O4 | 180.00 (10) | C10—C11—H11 | 120.5 |
| N2—Zn1—O4 | 92.36 (5) | C12—C11—H11 | 120.5 |
| N2i—Zn1—O4 | 87.64 (5) | C11—C12—C14 | 124.06 (13) |
| N2—Zn1—O4i | 87.64 (5) | C13—C12—C11 | 118.44 (13) |
| N2i—Zn1—O4i | 92.36 (5) | C13—C12—C14 | 117.28 (13) |
| N2i—Zn1—N2 | 180.00 (6) | N2—C13—C12 | 122.99 (13) |
| C1—O2—Zn1 | 127.55 (9) | N2—C13—H13 | 118.5 |
| Zn1—O4—H41 | 101.6 (16) | C12—C13—H13 | 118.5 |
| Zn1—O4—H42 | 135.9 (16) | O3—C14—N3 | 123.94 (14) |
| H41—O4—H42 | 106 (2) | O3—C14—C12 | 117.46 (14) |
| C9—N2—Zn1 | 122.37 (9) | N3—C14—C12 | 118.58 (13) |
| C9—N2—C13 | 118.12 (12) | N3—C15—C16 | 112.80 (17) |
| C13—N2—Zn1 | 119.50 (9) | N3—C15—H15A | 109.0 |
| C14—N3—C15 | 124.36 (14) | N3—C15—H15B | 109.0 |
| C14—N3—C17 | 118.81 (14) | C16—C15—H15A | 109.0 |
| C17—N3—C15 | 116.34 (14) | C16—C15—H15B | 109.0 |
| O1—C1—O2 | 126.05 (14) | H15A—C15—H15B | 107.8 |
| O1—C1—C2 | 117.65 (14) | C15—C16—H16A | 109.5 |
| O2—C1—C2 | 116.30 (13) | C15—C16—H16B | 109.5 |
| C3—C2—C1 | 120.47 (14) | C15—C16—H16C | 109.5 |
| C7—C2—C3 | 119.42 (14) | H16A—C16—H16B | 109.5 |
| C7—C2—C1 | 120.10 (13) | H16A—C16—H16C | 109.5 |
| C2—C3—H3 | 119.8 | H16B—C16—H16C | 109.5 |
| C4—C3—C2 | 120.43 (15) | N3—C17—C18 | 112.50 (18) |
| C4—C3—H3 | 119.8 | N3—C17—H17A | 109.1 |
| C3—C4—C5 | 119.49 (15) | N3—C17—H17B | 109.1 |
| C3—C4—H4 | 120.3 | C18—C17—H17A | 109.1 |
| C5—C4—H4 | 120.3 | C18—C17—H17B | 109.1 |
| C4—C5—C8 | 120.56 (16) | H17A—C17—H17B | 107.8 |
| C6—C5—C4 | 120.54 (15) | C17—C18—H18A | 109.5 |
| C6—C5—C8 | 118.90 (16) | C17—C18—H18B | 109.5 |
| C5—C6—C7 | 119.41 (15) | C17—C18—H18C | 109.5 |
| C5—C6—H6 | 120.3 | H18A—C18—H18B | 109.5 |
| C7—C6—H6 | 120.3 | H18A—C18—H18C | 109.5 |
| C2—C7—H7 | 119.7 | H18B—C18—H18C | 109.5 |
| C6—C7—C2 | 120.68 (15) | ||
| O4—Zn1—O2—C1 | 153.35 (13) | C15—N3—C17—C18 | 73.3 (2) |
| O4i—Zn1—O2—C1 | −26.65 (13) | O1—C1—C2—C3 | −8.8 (2) |
| N2—Zn1—O2—C1 | 60.99 (12) | O1—C1—C2—C7 | 170.29 (16) |
| N2i—Zn1—O2—C1 | −119.01 (12) | O2—C1—C2—C3 | 171.11 (15) |
| O2—Zn1—N2—C9 | −144.71 (12) | O2—C1—C2—C7 | −9.8 (2) |
| O2i—Zn1—N2—C9 | 35.29 (12) | C1—C2—C3—C4 | 177.77 (16) |
| O2—Zn1—N2—C13 | 34.08 (11) | C7—C2—C3—C4 | −1.4 (3) |
| O2i—Zn1—N2—C13 | −145.92 (11) | C1—C2—C7—C6 | −177.60 (15) |
| O4—Zn1—N2—C9 | 125.41 (12) | C3—C2—C7—C6 | 1.5 (2) |
| O4i—Zn1—N2—C9 | −54.59 (12) | C2—C3—C4—C5 | 0.0 (3) |
| O4—Zn1—N2—C13 | −55.80 (11) | C6—C5—C4—C3 | 1.2 (3) |
| O4i—Zn1—N2—C13 | 124.20 (11) | C8—C5—C4—C3 | −178.01 (18) |
| Zn1—O2—C1—O1 | 25.4 (2) | C4—C5—C6—C7 | −1.0 (3) |
| Zn1—O2—C1—C2 | −154.52 (10) | C8—C5—C6—C7 | 178.20 (17) |
| Zn1—N2—C9—C10 | 177.24 (12) | C2—C7—C6—C5 | −0.4 (3) |
| C13—N2—C9—C10 | −1.6 (2) | N2—C9—C10—C11 | −0.1 (2) |
| Zn1—N2—C13—C12 | −176.49 (11) | C12—C11—C10—C9 | 1.1 (2) |
| C9—N2—C13—C12 | 2.3 (2) | C13—C12—C11—C10 | −0.4 (2) |
| C15—N3—C14—O3 | −172.38 (18) | C14—C12—C11—C10 | 174.11 (15) |
| C15—N3—C14—C12 | 5.8 (2) | C11—C12—C14—O3 | −107.28 (19) |
| C17—N3—C14—O3 | −0.7 (3) | C11—C12—C14—N3 | 74.5 (2) |
| C17—N3—C14—C12 | 177.46 (14) | C13—C12—C14—O3 | 67.3 (2) |
| C14—N3—C15—C16 | −121.41 (19) | C13—C12—C14—N3 | −111.00 (17) |
| C17—N3—C15—C16 | 66.7 (2) | N2—C13—C12—C11 | −1.4 (2) |
| C14—N3—C17—C18 | −99.1 (2) | N2—C13—C12—C14 | −176.26 (13) |
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H41···O1i | 0.83 (2) | 1.84 (2) | 2.6419 (19) | 161 (2) |
| O4—H42···O3ii | 0.82 (2) | 2.03 (2) | 2.827 (2) | 163 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y−1, −z.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016013815/xu5890sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016013815/xu5890Isup2.hkl
CCDC reference: 1501337
Additional supporting information: crystallographic information; 3D view; checkCIF report