metal-organic compounds
Diaqua{μ2-N,N′-bis[(cyclohexanylidene)amino]oxamide}bis(triphenylphosphane)silver(I) dinitrate
aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: yupa.t@psu.ac.th
The dinuclear title compound, [Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2, lies across an inversion center and consists of two [Ag(H2O)(PPh3)] units bridged by a bis(cyclohexanone)oxalydihydrazone ligand. The charge-balance is supplied by two nitrate anions. The symmetry-unique AgI ion is in a distorted tetrahedral geometry coordinated by a P atom from a triphenylphosphane ligand, an O atom from a water molecule and a bis(cyclohexanone)oxalydihydrazone ligand bidentate chelating through the O atom and one of N atoms. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the components, forming chains along the b-axis direction. These chains are connected through weak C—H⋯O hydrogen bonds, leading to the formation of a two-dimensional supramolecular network parallel to (001).
CCDC reference: 978377
Related literature
For potential applications of hydrazone derivatives, see: Fouda et al. (2007); Qu et al. (2011); van der Star et al. (2012). For the use of metal(I) complexes of phosphine ligands as precursors for the preparation of mixed-ligand complexes, see: Nawaz et al. (2011); Pakawatchai et al. (2012). For a related structure, see: Wattanakanjana et al. (2013).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2012); cell SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008), SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 978377
10.1107/S1600536813034454/lh5679sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813034454/lh5679Isup2.hkl
Bis(cyclohexanone)oxalydihydrazone, BCO, (0.16g,0.58 mmol) was dissolved in 30 cm3 of methanol at 332 K. AgNO3 (0.10g,0.59 mmol) was added and the mixture was stirred for 3 hours. Triphenylphosphine, PPh3, (0.31g,1.18 mmol) was added and new reaction mixture was heated under reflux for 2 hours. The resulting clear solution was filtered off and left to evaporate at room temperature. Colorless crystals, which were deposited upon standing for 6 days, were filtered off and dried under reduced pressure.
H atoms bonded to C and N atoms were included in calculated positions with C—H = 0.95–0.99Å, N—H = 0.88Å and refined in a riding-model approximation with Uiso(H) = 1.2Ueq(C,N). The H atoms of the water molecules were included 'as found' positions with 1.5Ueq(O).
Studies of hydrazone derivatives containing nitrogen and oxygen have recently attracted considerable attention because not only are they corrosion inhibitors but it has been discovered that they are effective in different types of media (Fouda et al., 2007; Qu et al., 2011). They are an invaluable tool for studying mechanisms of acquired demyelination and remyelination which are histological hallmarks of multiple sclerosis (MS) (van der Star et al., 2012). Silver(I) complexes of phosphine ligands have been extensively studied as precursors for preparing mixed-ligand complexes having different geometries such as mononuclear and dinuclear (Nawaz et al., 2011; Pakawatchai et al., 2012). Here, we report the
of the title compound.The molecular structure of the title compound is shown in Fig. 1. The symmetry unique AgI ion is coordinated to the P atom of a triphenylphosphane ligand and the O atom of water molecule which forms the [Ag(H2O)(PPh3)] units. The bis(cyclohexanone)oxalydihydrazone ligand, located on an inversion center, acts as a bidentate bridging ligand between the two [Ag(H2O)(PPh3)] units by way of one O atom and one N atom. The AgI ion displays a distorted tetrahedral coordination. The P1—Ag1 bond length of 2.3369 (4) Å is shorter than that found in for example [Ag2Cl2(CH5N3S)2(C18H15P)2], which is 2.4225 (4) Å (Wattanakanjana et al., 2013). In the crystal, hydrogen bonds play a key role stabilizing a 2-D network. Intermolecular O—H···O hydrogen bonds occur where the oxygen atoms of nitrate anions serve as acceptors while H atoms of water molecules act as donors (Table 1). In addition, a pair of O—H···O hydrogen bonds form a four-membered O2H2 ring within a 1-D chain along [010] (Fig. 2). The chains are connected through weak C—H···O hydrogen bonds leading to the formation of a 2-D supramolecular network parallel to (001) as shown in Figure 3.
For potential applications of hydrazone derivatives, see: Fouda et al. (2007); Qu et al. (2011); van der Star et al. (2012). For the use of metal(I) complexes of phosphine ligands as precursors for the preparation of mixed-ligand complexes, see: Nawaz et al. (2011); Pakawatchai et al. (2012). For a related structure, see: Wattanakanjana et al. (2013).
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008), SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. The molecular structure with displacement ellipsoids drawn at the 30% probability level. Only the symmetry unique anion is shown and the asymmetric unit labelled. | |
Fig. 2. Part of the crystal structure of [{Ag(H2O)(C18H15P)}2(C14H22N4O2)]·(NO3)2 with O—H···O hydrogen bonds (red dashed lines) showing 1-D chain along [010] axis. | |
Fig. 3. A Fragment of the 2-D network of [{Ag(H2O)(C18H15P)}2(C14H22N4O2)]·(NO3)2, showing C—H···O hydrogen bonds viewed along the a axis. |
[Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2 | Z = 1 |
Mr = 1178.68 | F(000) = 602 |
Triclinic, P1 | Dx = 1.570 Mg m−3 |
a = 9.0903 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5730 (8) Å | Cell parameters from 6878 reflections |
c = 15.2638 (13) Å | θ = 2.3–31.3° |
α = 74.617 (1)° | µ = 0.91 mm−1 |
β = 83.676 (1)° | T = 100 K |
γ = 77.091 (1)° | Plate, colourless |
V = 1246.49 (18) Å3 | 0.42 × 0.38 × 0.10 mm |
Bruker SMART APEX CCD diffractometer | 7076 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.032 |
φ and ω scans | θmax = 31.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −13→13 |
Tmin = 0.624, Tmax = 0.746 | k = −13→13 |
29613 measured reflections | l = −22→22 |
7621 independent 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)] = 0.028 | Hydrogen site location: mixed |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.444P] where P = (Fo2 + 2Fc2)/3 |
7621 reflections | (Δ/σ)max = 0.001 |
313 parameters | Δρmax = 1.50 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
[Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2 | γ = 77.091 (1)° |
Mr = 1178.68 | V = 1246.49 (18) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.0903 (8) Å | Mo Kα radiation |
b = 9.5730 (8) Å | µ = 0.91 mm−1 |
c = 15.2638 (13) Å | T = 100 K |
α = 74.617 (1)° | 0.42 × 0.38 × 0.10 mm |
β = 83.676 (1)° |
Bruker SMART APEX CCD diffractometer | 7621 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 7076 reflections with I > 2σ(I) |
Tmin = 0.624, Tmax = 0.746 | Rint = 0.032 |
29613 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.50 e Å−3 |
7621 reflections | Δρmin = −0.54 e Å−3 |
313 parameters |
Experimental. Reflections 0 0 1 was affected by the beam stop and was omitted from the refinement. |
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 | ||
Ag1 | 0.77397 (2) | 0.67531 (2) | 0.14033 (2) | 0.01512 (4) | |
P1 | 0.87389 (4) | 0.59821 (4) | 0.28403 (3) | 0.01204 (7) | |
O1 | 0.58233 (10) | 0.91020 (10) | 0.10413 (6) | 0.0182 (2) | |
O2 | 0.60176 (10) | 0.57786 (10) | 0.07530 (6) | 0.0278 (3) | |
H2A | 0.5453 | 0.5216 | 0.0951 | 0.042* | |
H2B | 0.5935 | 0.5990 | 0.0158 | 0.042* | |
O3 | 0.41980 (18) | 0.36454 (16) | 0.11758 (9) | 0.0311 (3) | |
O4 | 0.46973 (17) | 0.30464 (18) | 0.26020 (10) | 0.0327 (3) | |
O5 | 0.37588 (17) | 0.15741 (16) | 0.20689 (9) | 0.0289 (3) | |
N1 | 0.67258 (14) | 0.90320 (14) | −0.04115 (9) | 0.0146 (2) | |
H1 | 0.6597 | 0.9387 | −0.0998 | 0.017* | |
N2 | 0.80176 (14) | 0.79893 (14) | −0.00875 (9) | 0.0144 (2) | |
N3 | 0.42173 (16) | 0.27494 (17) | 0.19571 (10) | 0.0211 (3) | |
C1 | 0.56953 (16) | 0.94638 (16) | 0.02131 (10) | 0.0132 (3) | |
C2 | 0.91980 (17) | 0.79182 (17) | −0.06359 (10) | 0.0160 (3) | |
C3 | 0.93888 (19) | 0.88935 (19) | −0.15685 (11) | 0.0203 (3) | |
H3A | 0.8466 | 0.9672 | −0.1707 | 0.024* | |
H3B | 0.9540 | 0.8301 | −0.2025 | 0.024* | |
C4 | 1.0763 (2) | 0.96139 (19) | −0.16206 (12) | 0.0220 (3) | |
H4A | 1.0959 | 1.0152 | −0.2258 | 0.026* | |
H4B | 1.0528 | 1.0343 | −0.1245 | 0.026* | |
C5 | 1.21787 (19) | 0.8478 (2) | −0.12903 (12) | 0.0222 (3) | |
H5A | 1.2474 | 0.7802 | −0.1699 | 0.027* | |
H5B | 1.3020 | 0.8989 | −0.1309 | 0.027* | |
C6 | 1.19021 (19) | 0.75881 (19) | −0.03247 (12) | 0.0210 (3) | |
H6A | 1.1659 | 0.8255 | 0.0091 | 0.025* | |
H6B | 1.2827 | 0.6846 | −0.0123 | 0.025* | |
C7 | 1.05827 (18) | 0.68022 (18) | −0.02872 (11) | 0.0185 (3) | |
H7A | 1.0861 | 0.6074 | −0.0663 | 0.022* | |
H7B | 1.0371 | 0.6264 | 0.0348 | 0.022* | |
C11 | 0.74414 (17) | 0.67524 (18) | 0.36679 (11) | 0.0163 (3) | |
C12 | 0.66381 (18) | 0.82024 (19) | 0.33780 (12) | 0.0204 (3) | |
H12 | 0.6780 | 0.8747 | 0.2768 | 0.024* | |
C13 | 0.5628 (2) | 0.8854 (2) | 0.39823 (15) | 0.0289 (4) | |
H13 | 0.5084 | 0.9842 | 0.3786 | 0.035* | |
C14 | 0.5425 (2) | 0.8049 (3) | 0.48700 (15) | 0.0347 (5) | |
H14 | 0.4741 | 0.8492 | 0.5284 | 0.042* | |
C15 | 0.6211 (2) | 0.6599 (3) | 0.51627 (14) | 0.0338 (4) | |
H15 | 0.6058 | 0.6054 | 0.5772 | 0.041* | |
C16 | 0.7224 (2) | 0.5946 (2) | 0.45616 (12) | 0.0244 (3) | |
H16 | 0.7765 | 0.4957 | 0.4759 | 0.029* | |
C21 | 0.91018 (18) | 0.39933 (16) | 0.33027 (10) | 0.0146 (3) | |
C22 | 0.7932 (2) | 0.32645 (19) | 0.32916 (11) | 0.0201 (3) | |
H22 | 0.6984 | 0.3814 | 0.3067 | 0.024* | |
C23 | 0.8160 (2) | 0.1736 (2) | 0.36097 (12) | 0.0262 (4) | |
H23 | 0.7362 | 0.1240 | 0.3613 | 0.031* | |
C24 | 0.9551 (3) | 0.0933 (2) | 0.39231 (13) | 0.0297 (4) | |
H24 | 0.9703 | −0.0113 | 0.4139 | 0.036* | |
C25 | 1.0718 (3) | 0.1643 (2) | 0.39229 (14) | 0.0309 (4) | |
H25 | 1.1671 | 0.1084 | 0.4132 | 0.037* | |
C26 | 1.0499 (2) | 0.31784 (19) | 0.36159 (12) | 0.0222 (3) | |
H26 | 1.1299 | 0.3667 | 0.3620 | 0.027* | |
C31 | 1.05027 (17) | 0.65300 (16) | 0.29052 (11) | 0.0152 (3) | |
C32 | 1.07908 (19) | 0.70550 (18) | 0.36258 (12) | 0.0204 (3) | |
H32 | 1.0065 | 0.7101 | 0.4120 | 0.025* | |
C33 | 1.2145 (2) | 0.7513 (2) | 0.36192 (15) | 0.0296 (4) | |
H33 | 1.2338 | 0.7877 | 0.4108 | 0.036* | |
C34 | 1.3209 (2) | 0.7438 (2) | 0.29016 (16) | 0.0337 (4) | |
H34 | 1.4121 | 0.7769 | 0.2895 | 0.040* | |
C35 | 1.2953 (2) | 0.6887 (3) | 0.21933 (15) | 0.0322 (4) | |
H35 | 1.3696 | 0.6816 | 0.1709 | 0.039* | |
C36 | 1.1601 (2) | 0.6437 (2) | 0.21948 (13) | 0.0243 (3) | |
H36 | 1.1421 | 0.6062 | 0.1708 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.01432 (6) | 0.01811 (6) | 0.01070 (6) | 0.00005 (4) | −0.00308 (4) | −0.00155 (4) |
P1 | 0.01111 (16) | 0.01418 (16) | 0.01055 (16) | −0.00195 (13) | −0.00170 (12) | −0.00267 (13) |
O1 | 0.0195 (5) | 0.0194 (5) | 0.0129 (5) | 0.0032 (4) | −0.0034 (4) | −0.0040 (4) |
O2 | 0.0328 (7) | 0.0370 (7) | 0.0208 (6) | −0.0188 (6) | −0.0022 (5) | −0.0096 (5) |
O3 | 0.0411 (8) | 0.0359 (7) | 0.0194 (6) | −0.0171 (6) | −0.0039 (6) | −0.0038 (5) |
O4 | 0.0329 (7) | 0.0479 (9) | 0.0250 (7) | −0.0109 (6) | −0.0062 (6) | −0.0180 (6) |
O5 | 0.0355 (7) | 0.0358 (7) | 0.0203 (6) | −0.0179 (6) | 0.0022 (5) | −0.0078 (5) |
N1 | 0.0128 (6) | 0.0159 (6) | 0.0118 (5) | 0.0001 (5) | −0.0018 (4) | 0.0000 (5) |
N2 | 0.0106 (5) | 0.0161 (6) | 0.0137 (6) | 0.0000 (4) | −0.0011 (4) | −0.0010 (5) |
N3 | 0.0161 (6) | 0.0308 (7) | 0.0187 (6) | −0.0047 (6) | 0.0005 (5) | −0.0107 (6) |
C1 | 0.0121 (6) | 0.0127 (6) | 0.0146 (6) | −0.0020 (5) | −0.0030 (5) | −0.0023 (5) |
C2 | 0.0140 (7) | 0.0186 (7) | 0.0151 (7) | −0.0040 (5) | −0.0003 (5) | −0.0034 (5) |
C3 | 0.0171 (7) | 0.0265 (8) | 0.0140 (7) | −0.0055 (6) | 0.0016 (5) | 0.0005 (6) |
C4 | 0.0216 (8) | 0.0230 (8) | 0.0205 (8) | −0.0075 (6) | 0.0036 (6) | −0.0033 (6) |
C5 | 0.0177 (7) | 0.0277 (8) | 0.0237 (8) | −0.0084 (6) | 0.0026 (6) | −0.0092 (7) |
C6 | 0.0151 (7) | 0.0267 (8) | 0.0219 (8) | −0.0028 (6) | −0.0003 (6) | −0.0088 (6) |
C7 | 0.0139 (7) | 0.0193 (7) | 0.0203 (7) | −0.0008 (6) | −0.0003 (6) | −0.0041 (6) |
C11 | 0.0124 (6) | 0.0231 (7) | 0.0168 (7) | −0.0053 (6) | 0.0005 (5) | −0.0095 (6) |
C12 | 0.0148 (7) | 0.0222 (7) | 0.0286 (8) | −0.0055 (6) | 0.0001 (6) | −0.0131 (7) |
C13 | 0.0178 (8) | 0.0323 (9) | 0.0458 (11) | −0.0070 (7) | 0.0044 (7) | −0.0266 (9) |
C14 | 0.0253 (9) | 0.0514 (12) | 0.0426 (11) | −0.0163 (9) | 0.0126 (8) | −0.0367 (10) |
C15 | 0.0325 (10) | 0.0552 (13) | 0.0228 (9) | −0.0190 (9) | 0.0096 (7) | −0.0213 (9) |
C16 | 0.0246 (8) | 0.0339 (9) | 0.0160 (7) | −0.0081 (7) | 0.0016 (6) | −0.0079 (7) |
C21 | 0.0181 (7) | 0.0148 (6) | 0.0109 (6) | −0.0044 (5) | −0.0003 (5) | −0.0022 (5) |
C22 | 0.0209 (8) | 0.0215 (7) | 0.0201 (7) | −0.0086 (6) | 0.0028 (6) | −0.0069 (6) |
C23 | 0.0357 (10) | 0.0241 (8) | 0.0231 (8) | −0.0164 (7) | 0.0103 (7) | −0.0094 (7) |
C24 | 0.0493 (12) | 0.0160 (7) | 0.0212 (8) | −0.0078 (8) | 0.0020 (8) | −0.0008 (6) |
C25 | 0.0383 (11) | 0.0196 (8) | 0.0289 (9) | 0.0019 (7) | −0.0101 (8) | 0.0010 (7) |
C26 | 0.0249 (8) | 0.0183 (7) | 0.0213 (8) | −0.0020 (6) | −0.0074 (6) | −0.0005 (6) |
C31 | 0.0128 (6) | 0.0141 (6) | 0.0180 (7) | −0.0027 (5) | −0.0029 (5) | −0.0021 (5) |
C32 | 0.0175 (7) | 0.0209 (7) | 0.0248 (8) | −0.0042 (6) | −0.0044 (6) | −0.0073 (6) |
C33 | 0.0219 (8) | 0.0336 (10) | 0.0408 (11) | −0.0080 (7) | −0.0083 (8) | −0.0173 (8) |
C34 | 0.0171 (8) | 0.0388 (11) | 0.0508 (13) | −0.0101 (8) | −0.0037 (8) | −0.0163 (9) |
C35 | 0.0167 (8) | 0.0450 (11) | 0.0377 (11) | −0.0099 (8) | 0.0055 (7) | −0.0147 (9) |
C36 | 0.0175 (8) | 0.0337 (9) | 0.0253 (8) | −0.0082 (7) | 0.0026 (6) | −0.0123 (7) |
Ag1—N2 | 2.2849 (13) | C11—C16 | 1.395 (2) |
Ag1—P1 | 2.3369 (4) | C11—C12 | 1.396 (2) |
Ag1—O2 | 2.4068 | C12—C13 | 1.395 (2) |
Ag1—O1 | 2.4898 (9) | C12—H12 | 0.9500 |
P1—C21 | 1.8137 (15) | C13—C14 | 1.385 (3) |
P1—C31 | 1.8149 (16) | C13—H13 | 0.9500 |
P1—C11 | 1.8187 (16) | C14—C15 | 1.391 (3) |
O1—C1 | 1.2304 (17) | C14—H14 | 0.9500 |
O2—H2A | 0.8048 | C15—C16 | 1.393 (3) |
O2—H2B | 0.8848 | C15—H15 | 0.9500 |
O3—N3 | 1.270 (2) | C16—H16 | 0.9500 |
O4—N3 | 1.2404 (19) | C21—C26 | 1.394 (2) |
O5—N3 | 1.249 (2) | C21—C22 | 1.400 (2) |
N1—C1 | 1.340 (2) | C22—C23 | 1.389 (2) |
N1—N2 | 1.4008 (17) | C22—H22 | 0.9500 |
N1—H1 | 0.8800 | C23—C24 | 1.387 (3) |
N2—C2 | 1.287 (2) | C23—H23 | 0.9500 |
C1—C1i | 1.524 (3) | C24—C25 | 1.382 (3) |
C2—C3 | 1.497 (2) | C24—H24 | 0.9500 |
C2—C7 | 1.501 (2) | C25—C26 | 1.394 (2) |
C3—C4 | 1.542 (2) | C25—H25 | 0.9500 |
C3—H3A | 0.9900 | C26—H26 | 0.9500 |
C3—H3B | 0.9900 | C31—C32 | 1.395 (2) |
C4—C5 | 1.523 (2) | C31—C36 | 1.398 (2) |
C4—H4A | 0.9900 | C32—C33 | 1.394 (2) |
C4—H4B | 0.9900 | C32—H32 | 0.9500 |
C5—C6 | 1.519 (2) | C33—C34 | 1.385 (3) |
C5—H5A | 0.9900 | C33—H33 | 0.9500 |
C5—H5B | 0.9900 | C34—C35 | 1.384 (3) |
C6—C7 | 1.541 (2) | C34—H34 | 0.9500 |
C6—H6A | 0.9900 | C35—C36 | 1.390 (3) |
C6—H6B | 0.9900 | C35—H35 | 0.9500 |
C7—H7A | 0.9900 | C36—H36 | 0.9500 |
C7—H7B | 0.9900 | ||
N2—Ag1—P1 | 146.83 (3) | C2—C7—H7B | 109.7 |
N2—Ag1—O2 | 80.48 (4) | C6—C7—H7B | 109.7 |
P1—Ag1—O2 | 130.70 (2) | H7A—C7—H7B | 108.2 |
N2—Ag1—O1 | 69.04 (4) | C16—C11—C12 | 120.00 (15) |
P1—Ag1—O1 | 118.43 (2) | C16—C11—P1 | 122.44 (13) |
O2—Ag1—O1 | 84.40 (3) | C12—C11—P1 | 117.56 (12) |
C21—P1—C31 | 105.26 (7) | C13—C12—C11 | 120.17 (17) |
C21—P1—C11 | 105.67 (7) | C13—C12—H12 | 119.9 |
C31—P1—C11 | 104.89 (7) | C11—C12—H12 | 119.9 |
C21—P1—Ag1 | 113.89 (5) | C14—C13—C12 | 119.49 (19) |
C31—P1—Ag1 | 115.29 (5) | C14—C13—H13 | 120.3 |
C11—P1—Ag1 | 110.99 (5) | C12—C13—H13 | 120.3 |
C1—O1—Ag1 | 107.71 (8) | C13—C14—C15 | 120.72 (17) |
Ag1—O2—H2A | 135.1 | C13—C14—H14 | 119.6 |
Ag1—O2—H2B | 121.5 | C15—C14—H14 | 119.6 |
H2A—O2—H2B | 103.3 | C14—C15—C16 | 119.94 (19) |
C1—N1—N2 | 116.91 (12) | C14—C15—H15 | 120.0 |
C1—N1—H1 | 121.5 | C16—C15—H15 | 120.0 |
N2—N1—H1 | 121.5 | C15—C16—C11 | 119.67 (19) |
C2—N2—N1 | 117.05 (13) | C15—C16—H16 | 120.2 |
C2—N2—Ag1 | 129.26 (11) | C11—C16—H16 | 120.2 |
N1—N2—Ag1 | 113.55 (9) | C26—C21—C22 | 119.82 (15) |
O4—N3—O5 | 120.55 (16) | C26—C21—P1 | 122.88 (12) |
O4—N3—O3 | 119.69 (16) | C22—C21—P1 | 117.21 (12) |
O5—N3—O3 | 119.76 (14) | C23—C22—C21 | 119.81 (17) |
O1—C1—N1 | 125.99 (13) | C23—C22—H22 | 120.1 |
O1—C1—C1i | 121.54 (17) | C21—C22—H22 | 120.1 |
N1—C1—C1i | 112.43 (16) | C24—C23—C22 | 120.06 (17) |
N2—C2—C3 | 127.37 (15) | C24—C23—H23 | 120.0 |
N2—C2—C7 | 117.00 (14) | C22—C23—H23 | 120.0 |
C3—C2—C7 | 115.50 (13) | C25—C24—C23 | 120.41 (16) |
C2—C3—C4 | 109.85 (14) | C25—C24—H24 | 119.8 |
C2—C3—H3A | 109.7 | C23—C24—H24 | 119.8 |
C4—C3—H3A | 109.7 | C24—C25—C26 | 120.14 (18) |
C2—C3—H3B | 109.7 | C24—C25—H25 | 119.9 |
C4—C3—H3B | 109.7 | C26—C25—H25 | 119.9 |
H3A—C3—H3B | 108.2 | C21—C26—C25 | 119.75 (17) |
C5—C4—C3 | 112.15 (14) | C21—C26—H26 | 120.1 |
C5—C4—H4A | 109.2 | C25—C26—H26 | 120.1 |
C3—C4—H4A | 109.2 | C32—C31—C36 | 119.17 (15) |
C5—C4—H4B | 109.2 | C32—C31—P1 | 122.66 (12) |
C3—C4—H4B | 109.2 | C36—C31—P1 | 118.16 (12) |
H4A—C4—H4B | 107.9 | C33—C32—C31 | 119.95 (17) |
C6—C5—C4 | 110.70 (14) | C33—C32—H32 | 120.0 |
C6—C5—H5A | 109.5 | C31—C32—H32 | 120.0 |
C4—C5—H5A | 109.5 | C34—C33—C32 | 120.11 (18) |
C6—C5—H5B | 109.5 | C34—C33—H33 | 119.9 |
C4—C5—H5B | 109.5 | C32—C33—H33 | 119.9 |
H5A—C5—H5B | 108.1 | C35—C34—C33 | 120.54 (17) |
C5—C6—C7 | 109.82 (14) | C35—C34—H34 | 119.7 |
C5—C6—H6A | 109.7 | C33—C34—H34 | 119.7 |
C7—C6—H6A | 109.7 | C34—C35—C36 | 119.52 (18) |
C5—C6—H6B | 109.7 | C34—C35—H35 | 120.2 |
C7—C6—H6B | 109.7 | C36—C35—H35 | 120.2 |
H6A—C6—H6B | 108.2 | C35—C36—C31 | 120.69 (17) |
C2—C7—C6 | 109.86 (13) | C35—C36—H36 | 119.7 |
C2—C7—H7A | 109.7 | C31—C36—H36 | 119.7 |
C6—C7—H7A | 109.7 | ||
C1—N1—N2—C2 | −158.29 (14) | C12—C11—C16—C15 | −0.4 (3) |
C1—N1—N2—Ag1 | 17.79 (16) | P1—C11—C16—C15 | −179.89 (14) |
Ag1—O1—C1—N1 | −22.20 (17) | C31—P1—C21—C26 | −0.36 (16) |
Ag1—O1—C1—C1i | 160.03 (15) | C11—P1—C21—C26 | −111.04 (14) |
N2—N1—C1—O1 | 5.0 (2) | Ag1—P1—C21—C26 | 126.88 (13) |
N2—N1—C1—C1i | −177.05 (14) | C31—P1—C21—C22 | −176.91 (12) |
N1—N2—C2—C3 | 4.3 (2) | C11—P1—C21—C22 | 72.41 (13) |
Ag1—N2—C2—C3 | −171.05 (12) | Ag1—P1—C21—C22 | −49.67 (13) |
N1—N2—C2—C7 | 179.89 (13) | C26—C21—C22—C23 | 1.3 (2) |
Ag1—N2—C2—C7 | 4.5 (2) | P1—C21—C22—C23 | 177.95 (13) |
N2—C2—C3—C4 | 123.63 (18) | C21—C22—C23—C24 | −1.1 (3) |
C7—C2—C3—C4 | −52.01 (19) | C22—C23—C24—C25 | 0.1 (3) |
C2—C3—C4—C5 | 51.65 (19) | C23—C24—C25—C26 | 0.7 (3) |
C3—C4—C5—C6 | −56.69 (19) | C22—C21—C26—C25 | −0.5 (3) |
C4—C5—C6—C7 | 58.54 (18) | P1—C21—C26—C25 | −176.97 (14) |
N2—C2—C7—C6 | −121.04 (16) | C24—C25—C26—C21 | −0.5 (3) |
C3—C2—C7—C6 | 55.07 (19) | C21—P1—C31—C32 | −95.87 (14) |
C5—C6—C7—C2 | −56.55 (18) | C11—P1—C31—C32 | 15.37 (15) |
C21—P1—C11—C16 | 17.38 (16) | Ag1—P1—C31—C32 | 137.74 (12) |
C31—P1—C11—C16 | −93.57 (15) | C21—P1—C31—C36 | 85.04 (14) |
Ag1—P1—C11—C16 | 141.31 (13) | C11—P1—C31—C36 | −163.72 (13) |
C21—P1—C11—C12 | −162.09 (12) | Ag1—P1—C31—C36 | −41.35 (15) |
C31—P1—C11—C12 | 86.96 (13) | C36—C31—C32—C33 | 1.6 (3) |
Ag1—P1—C11—C12 | −38.16 (13) | P1—C31—C32—C33 | −177.50 (14) |
C16—C11—C12—C13 | 0.6 (2) | C31—C32—C33—C34 | −0.4 (3) |
P1—C11—C12—C13 | −179.91 (13) | C32—C33—C34—C35 | −1.1 (3) |
C11—C12—C13—C14 | −0.2 (3) | C33—C34—C35—C36 | 1.5 (3) |
C12—C13—C14—C15 | −0.3 (3) | C34—C35—C36—C31 | −0.3 (3) |
C13—C14—C15—C16 | 0.5 (3) | C32—C31—C36—C35 | −1.2 (3) |
C14—C15—C16—C11 | −0.1 (3) | P1—C31—C36—C35 | 177.89 (16) |
Symmetry code: (i) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.80 | 2.02 | 2.8103 (17) | 167 |
O2—H2B···O3ii | 0.88 | 1.98 | 2.8684 (16) | 177 |
N1—H1···O5ii | 0.88 | 2.16 | 2.8407 (19) | 134 |
C22—H22···O4 | 0.95 | 2.58 | 3.297 (2) | 133 |
Symmetry code: (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.80 | 2.02 | 2.8103 (17) | 166.5 |
O2—H2B···O3i | 0.88 | 1.98 | 2.8684 (16) | 176.9 |
N1—H1···O5i | 0.88 | 2.16 | 2.8407 (19) | 133.6 |
C22—H22···O4 | 0.95 | 2.58 | 3.297 (2) | 132.6 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
Financial support from the Center of Excellence for Innovation in Chemistry (PERCH–CIC), the Office of the Higher Education Commission, Ministry of Education, and the Department of Chemistry, Prince of Songkla University, is gratefully acknowledged. RN would like to thank Dr Matthias Zeller for valuable suggestions and assistance with the X-ray
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Studies of hydrazone derivatives containing nitrogen and oxygen have recently attracted considerable attention because not only are they corrosion inhibitors but it has been discovered that they are effective in different types of media (Fouda et al., 2007; Qu et al., 2011). They are an invaluable tool for studying mechanisms of acquired demyelination and remyelination which are histological hallmarks of multiple sclerosis (MS) (van der Star et al., 2012). Silver(I) complexes of phosphine ligands have been extensively studied as precursors for preparing mixed-ligand complexes having different geometries such as mononuclear and dinuclear (Nawaz et al., 2011; Pakawatchai et al., 2012). Here, we report the crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. The symmetry unique AgI ion is coordinated to the P atom of a triphenylphosphane ligand and the O atom of water molecule which forms the [Ag(H2O)(PPh3)] units. The bis(cyclohexanone)oxalydihydrazone ligand, located on an inversion center, acts as a bidentate bridging ligand between the two [Ag(H2O)(PPh3)] units by way of one O atom and one N atom. The AgI ion displays a distorted tetrahedral coordination. The P1—Ag1 bond length of 2.3369 (4) Å is shorter than that found in for example [Ag2Cl2(CH5N3S)2(C18H15P)2], which is 2.4225 (4) Å (Wattanakanjana et al., 2013). In the crystal, hydrogen bonds play a key role stabilizing a 2-D network. Intermolecular O—H···O hydrogen bonds occur where the oxygen atoms of nitrate anions serve as acceptors while H atoms of water molecules act as donors (Table 1). In addition, a pair of O—H···O hydrogen bonds form a four-membered O2H2 ring within a 1-D chain along [010] (Fig. 2). The chains are connected through weak C—H···O hydrogen bonds leading to the formation of a 2-D supramolecular network parallel to (001) as shown in Figure 3.