research communications
[N′-(4-Decyloxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′]dimethyltin(IV): and Hirshfeld surface analysis
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, bResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, cDepartment of Chemistry, Lancaster University, Lancaster LA1 4YB, United Kingdom, and dDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India
*Correspondence e-mail: edwardt@sunway.edu.my
The title diorganotin compound, [Sn(CH3)2(C28H32N2O4)], features a distorted SnC2NO2 coordination geometry almost intermediate between ideal trigonal–bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion via two alkoxide O and hydrazinyl N atoms; an intramolecular hydroxy-O—H⋯N(hydrazinyl) hydrogen bond is noted. The alkoxy chain has an all-trans conformation, and to the first approximation, the molecule has local mirror symmetry relating the two Sn-bound methyl groups. Supramolecular layers sustained by imine-C—H⋯O(hydroxy), π–π [between decyloxy-substituted benzene rings with an inter-centroid separation of 3.7724 (13) Å], C—H⋯π(arene) and C—H⋯π(chelate ring) interactions are formed in the crystal; layers stack along the c axis with no directional interactions between them. The presence of C—H⋯π(chelate ring) interactions in the crystal is clearly evident from an analysis of the calculated Hirshfeld surface.
Keywords: crystal structure; organotin; Schiff base; Hirshfeld surface analysis.
CCDC reference: 1532445
1. Chemical context
Organotin(IV) compounds with Schiff base ligands have been actively studied because of their versatile chemistry, e.g. solution versus solid-state structures, and their potential as biologically active compounds such as in anti-cancer and anti-microbial applications (Davies et al., 2008; Nath & Saini, 2011). Among these Schiff base ligands, those derived from 3-hydroxy-2-napthoic hydrazide have long been known to have promising anti-microbial (Dogan et al., 1998b) and anti-convulsant activities (Dogan et al., 1998a). Subsequently, various organotin compounds derived from these Schiff base ligands have been prepared and their anti-cancer potential explored (Lee et al., 2012, 2013). These studies have revealed interesting biological activities and often correlations were possible with their solid-state structures (Lee et al., 2009, 2010). Complementary studies on vanadium complexes with these Schiff base ligands focused upon their urease inhibitory activities (You et al., 2012). In addition, the catalytic properties of vanadium (Hosseini-Monfared et al., 2010, 2014), cerium (Jiao et al., 2014) and palladium complexes (Arumugam et al., 2015) have been explored. Further, structural data for copper (Liu et al., 2012), molybdenum (Miao, 2012) and vanadium (Kurup et al., 2010) complexes are available. As part of our on-going work with these ONO tridentate ligands (Lee et al., 2013), we hereby describe the crystal and molecular structures of the title compound, (I), as well as a detailed analysis of the intermolecular associations through a Hirshfeld surface analysis.
2. Structural commentary
The tin(IV) atom in (I), Fig. 1, is complexed by a di-anionic, tridentate Schiff base ligand noteworthy for the appended fused-ring system and for the long alkoxy chain substituent. The five-coordinate geometry is completed by two Sn-bound methyl groups, Table 1. The resulting C2NO2 coordination geometry is highly distorted with the value of τ being 0.52, i.e. almost exactly intermediate between ideal square-pyramidal (τ = 0) and trigonal–bipyramidal (τ = 1.0) (Addison et al., 1984). The widest angle at the tin atom is subtended by the two alkoxide-O atoms, i.e. 157.14 (6)°, with the other angles ranging from an acute 73.16 (6)°, for O1—Sn—O2, to 125.89 (9)°, being subtended by the two Sn-bound methyl groups.
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The five-membered, SnON2C chelate ring is almost planar with a r.m.s. deviation of 0.0222 Å and in the same way, the six-membered, SnONC3 ring is close to planar with a r.m.s. deviation of 0.0155 Å; the dihedral angle between the chelate rings is small, being 2.90 (4)°. The bond lengths involving the nitrogen atoms comprising the backbone of the chelate rings suggest some conjugation, i.e. N1—C1, N1—N2 and N2—C12 are 1.317 (3), 1.397 (2) and 1.303 (3) Å, respectively. The 10 atoms of the fused-ring system appended to the five-membered chelate ring make a dihedral angle of 2.01 (3)° with the chelate ring, a conformation allowing the formation of an intramolecular hydroxy-O—H⋯N(hydrazinyl) hydrogen bond to close an S(6) loop, Table 2. The dihedral angle between the six-membered and fused benzene rings is 1.12 (5)°, indicating a strictly co-planar relationship. Significant planarity in the molecule is indicated by the dihedral angle of 5.84 (4)° between the appended fused-ring system at C1 and the fused benzene ring. In addition, the decyloxy side chain has an all-trans conformation with the range of torsion angles being −174.96 (18)°, for C21—C22—C23—C24, to 179.79 (19)°, for C25—C26—C27—C28. Indeed, the r.m.s. deviation for the least-squares plane through all non-hydrogen atoms except the Sn-bound methyl groups is relatively small at 0.1179 Å, with maximum deviations being for the terminal methyl group of the alkoxy chain, i.e. 0.296 (2) Å, and a central methylene-C22 atom, i.e. 0.194 (2) Å. Hence, to a first approximation, the molecule has mirror symmetry, relating the two Sn-bound methyl groups.
3. Supramolecular features
Aside from participating in an intramolecular hydroxy-O—H⋯N(hydrazinyl) hydrogen bond, the hydroxy-O atom accepts an interaction from a centrosymmetrically-related imine-H atom, Table 2. This has the result that a 16-membered {⋯OC3N2CH}2 synthon is formed, which encapsulates two six-membered {⋯HOC3N} synthons formed by the intramolecular hydroxy-O—H⋯N(hydrazinyl) hydrogen bonding mentioned above, Fig. 2a. Centrosymmetrically related dimeric aggregates are linked via π–π interactions between decyloxy-substituted benzene rings [inter-centroid separation = 3.7724 (13) Å for 1 − x, 1 − y, 1 − z]. The remaining interactions are of the type C—H⋯π and involve methylene-C—H exclusively. While two of the interactions have benzene rings as acceptors, the other two have chelate rings as acceptors, i.e. are of the type C—H⋯π(chelate), a phenomenon gaining increasing attention (Tiekink, 2017); Table 2. Taken alone, the C—H⋯π interactions lead to supramolecular chains as illustrated in Fig. 2b. The result of all of the identified intermolecular interactions is the formation of supramolecular layers that stack along the c axis with no directional interactions between them, Fig. 2c.
4. Hirshfeld surface analysis
The Hirshfeld surface analysis for (I) was performed as described in a recent publication of a related organotin structure (Mohamad et al., 2017). From the view of the Hirshfeld surface mapped over dnorm, in the range −0.053 to + 1.621 au, Fig. 3, the bright-red spots appearing near the hydroxy-O2 and imine-H12 atoms represent the acceptor and donor of the intermolecular C—H⋯O interaction forming the {⋯OC3N2CH}2 synthon as discussed in the previous section; these are also viewed as blue and red regions near the H and O atoms on the Hirshfeld surface mapped over electrostatic potential (over the range ± 0.075 au), Fig. 4, corresponding to positive and negative potentials, respectively. In the absence of more conventional hydrogen bonds in the packing of (I), the structure contains two types of C—H⋯π interactions. The donors and acceptors of the C—H⋯π(arene) contacts are also viewed as respective light-blue and red regions on the Hirshfeld surface mapped over electrostatic potential, Fig. 4. In Fig. 5, the bright-orange spots enclosed within the circles around chelate (blue circle) and benzene (red) rings on the de mapped Hirshfeld surface, Fig. 5, illustrate all acceptors of the C—H⋯π contacts. The immediate environment about a reference molecule within the Hirshfeld surface mapped with the shape-index property is illustrated in Fig. 6. The C—H⋯π(chelate) and C19—H19A⋯π(C13–C18) contacts at 1 − x, −y, 1 − z and their reciprocal contacts, i.e. π⋯H—C, are represented with blue and white dotted lines, respectively, in Fig. 6a. The other C—H⋯π contacts involving benzene rings and π–π stacking interactions at 1 − x, 1 − y, 1 − z are illustrated in Fig. 6b.
The overall two-dimensional fingerprint plot and those delineated into H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, N⋯H/H⋯N and C⋯C contacts (McKinnon et al., 2007) are illustrated in Fig. 7a–f; their relative contributions are summarized quantitatively in Table 3. The most notable observation from the Hirshfeld surface analysis of the structure of (I) is that hydrogen atoms are involved in the overwhelming majority of surface contacts, i.e. 97.0%.
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A pair of very short peaks at de + di ∼ 2.38 Å in the fingerprint plot delineated into H⋯H contacts, Fig. 7b, is due to a short interatomic contact between benzene-H18 and methylene-H25A atoms, Table 4. The involvement of methylene-H atoms in C—H⋯π interactions with the arene and chelate rings results in the second largest contribution to the overall Hirshfeld surface, i.e. 20.9%, in the form of C⋯H/H⋯C contacts, Fig. 7c. The short interatomic C⋯H/H⋯C contact between the ring-C18 and methylene-H19A atoms, Table 4, accounts for the presence of an interaction between these atoms. Another short interatomic C⋯H/H⋯C contact, namely C10⋯H18 (Table 4), is merged in the corresponding plot of Fig. 7c. The presence of two C—H⋯π(chelate) interactions, Table 2, can be easily recognized from the fingerprint plots delineated into C⋯H/H⋯C and N⋯H/H⋯N contacts, Fig. 7c and e, as their ring centroids (Cg1 and Cg2; Table 2) are close to the N and C atoms of the chelate rings and so provide discernible contributions to the Hirshfeld surface. A recent study also confirmed the impact of C—H⋯π(chelate) interactions upon the Hirshfeld surface of a metal-organic compound (Jotani et al., 2016). A pair of short spikes with tips at de + di ∼ 2.5 Å on the parabolic distribution of points around de + di ∼ 2.7 Å shown by a pair of red arcs in Fig. 7d are the result of C—H⋯O and short interatomic O⋯H/H⋯O contacts, Table 4. A small but recognizable contribution, i.e. 1.8%, from C⋯C contacts to the Hirshfeld surface is assigned to π–π stacking interactions between symmetry-related (C13–C18) benzene rings, and appears as an arrow-like distribution of points around de = di ∼ 1.9 Å in Fig. 7f. The other contacts, having low percentage contribution to the surface, are likely to have a negligible effect on the molecular packing.
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5. Database survey
According to a search of the crystallographic literature (Groom et al., 2016), there are approximately 100 diorganotin structures with Schiff base ligands having an O—C=N—N=C—C C—O backbone, as in (I). Of these, 13 have the 3-hydroxynaphthalene residue, reflecting the biological interest in these compounds (see Chemical context). Two dimethyltin structures are available with identical ligands apart from having a substituent in the 5-position, i.e. chloride (Lee et al., 2009) and bromide (Lee et al., 2010), rather than in the 4-position as for (I); the two halide structures are isostructural. An overlap diagram of (I) and the two 5-halide derivatives is shown in Fig. 8, which highlights the similarity between the structures. This borne out by the values of τ (Addison et al., 1984), i.e. 0.47 and 0.46 for the chloride and bromide structures, respectively, cf. 0.52 for (I).
6. Synthesis and crystallization
All chemicals and solvents were used as purchased without purification, and all reactions were carried out under ambient conditions. The melting point was determined using an Electrothermal digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Perkin Elmer Spectrum 400 FT Mid-IR/Far-IR spectrophotometer from 4000 to 400 cm−1. The 1H NMR spectrum was recorded at room temperature in DMSO-d6 solution on a Jeol ECA 400 MHz FT–NMR spectrometer.
N-(4-Decoxy-2-oxidobenzylidene)-3-hydroxy-2-napthohydrazide (1.0 mmol, 0.463 g) and triethylamine (1.0 mmol, 0.14 ml) in ethyl acetate (25 ml) were added to dimethyltin dichloride (1.0 mmol, 0.220 g) in ethyl acetate (10 ml). The resulting mixture was stirred and refluxed for 3 h. The filtrate was evaporated until a precipitate was obtained. The precipitate was recrystallized from dichloromethane:dimethylformamide (1:1), and yellow prismatic crystals suitable for X-ray crystallographic studies were obtained from the slow evaporation of the filtrate. Yield: 0.366 g, 60%; M.p.: 507–508 K. IR (cm−1): 3162(br), 1633(s), 1597(s), 1169(s) cm−1. 1H NMR (in DMSO-d6): δ 11.34 (s, 1H, –OH), 8.57 (s, 1H, –N=CH), 6.25–6.40, 7.07–7.20 (m, 8H, aromatic-H), 8.47 (s, 1H, aromatic-H), 3.96 (s, 2H, –OCH2–), 1.28-1.82 (m, 16H, –CH2–), 0.91, (s, 6H, Sn—CH3), 0.89 (s, 3H, –CH2CH3).
7. Refinement
Crystal data, data collection and structure . Carbon-bound H atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and were included in the in the riding-model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The oxygen-bound H atom was located in a difference Fourier map but was refined with a distance restraint of O—H = 0.84±0.01 Å, and with Uiso(H) set to 1.5Ueq(O). The maximum and minimum residual electron density peaks of 0.80 and 1.32 e Å−3 were located 0.42 and 0.83 Å, respectively, from the H23B and Sn atoms.
details are summarized in Table 5
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Supporting information
CCDC reference: 1532445
https://doi.org/10.1107/S2056989017002365/hb7655sup1.cif
contains datablock . DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017002365/hb7655Isup2.hkl
Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell
CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[Sn(CH3)2(C28H32N2O4)] | F(000) = 2512 |
Mr = 609.31 | Dx = 1.468 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 25.2622 (9) Å | Cell parameters from 14600 reflections |
b = 7.4543 (2) Å | θ = 2.9–29.3° |
c = 29.9819 (11) Å | µ = 0.96 mm−1 |
β = 102.349 (4)° | T = 100 K |
V = 5515.3 (3) Å3 | Prism, yellow |
Z = 8 | 0.26 × 0.21 × 0.09 mm |
Rigaku SuperNova, Dual, Mo at zero, AtlasS2 diffractometer | 7182 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 6371 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.038 |
ω scans | θmax = 29.7°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015) | h = −33→34 |
Tmin = 0.756, Tmax = 1.000 | k = −10→9 |
38191 measured reflections | l = −40→41 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0376P)2 + 14.285P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max = 0.006 |
S = 1.01 | Δρmax = 0.80 e Å−3 |
7182 reflections | Δρmin = −1.32 e Å−3 |
340 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn | 0.42928 (2) | 0.37591 (2) | 0.63968 (2) | 0.01137 (5) | |
O1 | 0.35465 (6) | 0.4300 (2) | 0.66140 (5) | 0.0167 (3) | |
O2 | 0.21397 (6) | 0.5277 (2) | 0.55907 (5) | 0.0183 (3) | |
H2O | 0.2451 (6) | 0.506 (4) | 0.5555 (10) | 0.027* | |
O3 | 0.47942 (6) | 0.3222 (2) | 0.59379 (5) | 0.0181 (3) | |
O4 | 0.54342 (6) | 0.2034 (2) | 0.45789 (5) | 0.0201 (3) | |
N1 | 0.31505 (7) | 0.4446 (2) | 0.58481 (6) | 0.0129 (3) | |
N2 | 0.36668 (7) | 0.3985 (2) | 0.57883 (6) | 0.0110 (3) | |
C1 | 0.31320 (8) | 0.4565 (3) | 0.62829 (7) | 0.0124 (4) | |
C2 | 0.26038 (8) | 0.5020 (3) | 0.63921 (7) | 0.0129 (4) | |
C3 | 0.25664 (8) | 0.5125 (3) | 0.68442 (7) | 0.0133 (4) | |
H3 | 0.2883 | 0.4944 | 0.7076 | 0.016* | |
C4 | 0.20706 (8) | 0.5496 (3) | 0.69711 (7) | 0.0146 (4) | |
C5 | 0.20297 (9) | 0.5598 (3) | 0.74350 (7) | 0.0188 (4) | |
H5 | 0.2345 | 0.5437 | 0.7669 | 0.023* | |
C6 | 0.15430 (9) | 0.5926 (3) | 0.75491 (8) | 0.0214 (5) | |
H6 | 0.1522 | 0.6003 | 0.7861 | 0.026* | |
C7 | 0.10712 (9) | 0.6150 (3) | 0.72021 (8) | 0.0204 (5) | |
H7 | 0.0733 | 0.6357 | 0.7284 | 0.025* | |
C8 | 0.10947 (9) | 0.6074 (3) | 0.67508 (8) | 0.0178 (4) | |
H8 | 0.0774 | 0.6232 | 0.6522 | 0.021* | |
C9 | 0.15978 (8) | 0.5758 (3) | 0.66226 (7) | 0.0146 (4) | |
C10 | 0.16431 (8) | 0.5697 (3) | 0.61610 (7) | 0.0150 (4) | |
H10 | 0.1331 | 0.5913 | 0.5927 | 0.018* | |
C11 | 0.21280 (8) | 0.5332 (3) | 0.60440 (7) | 0.0134 (4) | |
C12 | 0.37054 (8) | 0.3749 (3) | 0.53660 (7) | 0.0121 (4) | |
H12 | 0.3383 | 0.3905 | 0.5140 | 0.014* | |
C13 | 0.41771 (8) | 0.3285 (3) | 0.52079 (7) | 0.0126 (4) | |
C14 | 0.47001 (8) | 0.3039 (3) | 0.54913 (7) | 0.0131 (4) | |
C15 | 0.51337 (8) | 0.2588 (3) | 0.52845 (7) | 0.0143 (4) | |
H15 | 0.5486 | 0.2403 | 0.5468 | 0.017* | |
C16 | 0.50482 (8) | 0.2413 (3) | 0.48147 (7) | 0.0144 (4) | |
C17 | 0.45295 (9) | 0.2635 (3) | 0.45328 (7) | 0.0173 (4) | |
H17 | 0.4476 | 0.2495 | 0.4211 | 0.021* | |
C18 | 0.41073 (8) | 0.3053 (3) | 0.47295 (7) | 0.0154 (4) | |
H18 | 0.3756 | 0.3194 | 0.4541 | 0.018* | |
C19 | 0.59810 (8) | 0.1635 (3) | 0.48078 (7) | 0.0152 (4) | |
H19A | 0.5993 | 0.0624 | 0.5024 | 0.018* | |
H19B | 0.6158 | 0.2694 | 0.4976 | 0.018* | |
C20 | 0.62486 (9) | 0.1133 (3) | 0.44178 (7) | 0.0152 (4) | |
H20A | 0.6187 | 0.2127 | 0.4193 | 0.018* | |
H20B | 0.6060 | 0.0064 | 0.4264 | 0.018* | |
C21 | 0.68525 (8) | 0.0733 (3) | 0.45358 (7) | 0.0160 (4) | |
H21A | 0.6923 | −0.0341 | 0.4734 | 0.019* | |
H21B | 0.7051 | 0.1759 | 0.4703 | 0.019* | |
C22 | 0.70459 (8) | 0.0402 (3) | 0.40919 (7) | 0.0159 (4) | |
H22A | 0.6830 | −0.0595 | 0.3927 | 0.019* | |
H22B | 0.6964 | 0.1487 | 0.3899 | 0.019* | |
C23 | 0.76433 (8) | −0.0045 (3) | 0.41369 (7) | 0.0156 (4) | |
H23A | 0.7726 | −0.1202 | 0.4299 | 0.019* | |
H23B | 0.7868 | 0.0896 | 0.4319 | 0.019* | |
C24 | 0.77803 (8) | −0.0168 (3) | 0.36659 (7) | 0.0152 (4) | |
H24A | 0.7549 | −0.1105 | 0.3488 | 0.018* | |
H24B | 0.7687 | 0.0988 | 0.3506 | 0.018* | |
C25 | 0.83719 (9) | −0.0601 (3) | 0.36696 (7) | 0.0167 (4) | |
H25A | 0.8465 | −0.1774 | 0.3821 | 0.020* | |
H25B | 0.8606 | 0.0321 | 0.3851 | 0.020* | |
C26 | 0.84886 (8) | −0.0668 (3) | 0.31918 (7) | 0.0151 (4) | |
H26A | 0.8271 | −0.1642 | 0.3017 | 0.018* | |
H26B | 0.8372 | 0.0477 | 0.3034 | 0.018* | |
C27 | 0.90843 (9) | −0.0980 (3) | 0.31902 (7) | 0.0174 (4) | |
H27A | 0.9303 | −0.0004 | 0.3362 | 0.021* | |
H27B | 0.9203 | −0.2125 | 0.3348 | 0.021* | |
C28 | 0.91884 (9) | −0.1048 (3) | 0.27092 (8) | 0.0207 (5) | |
H28A | 0.8977 | −0.2027 | 0.2539 | 0.031* | |
H28B | 0.9575 | −0.1255 | 0.2725 | 0.031* | |
H28C | 0.9080 | 0.0093 | 0.2554 | 0.031* | |
C29 | 0.44335 (10) | 0.1248 (3) | 0.67269 (8) | 0.0199 (4) | |
H29A | 0.4669 | 0.0522 | 0.6578 | 0.030* | |
H29B | 0.4088 | 0.0626 | 0.6708 | 0.030* | |
H29C | 0.4609 | 0.1430 | 0.7048 | 0.030* | |
C30 | 0.46626 (9) | 0.6203 (3) | 0.66410 (8) | 0.0199 (4) | |
H30A | 0.5018 | 0.5964 | 0.6838 | 0.030* | |
H30B | 0.4434 | 0.6835 | 0.6816 | 0.030* | |
H30C | 0.4708 | 0.6948 | 0.6382 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn | 0.00732 (7) | 0.01518 (8) | 0.01046 (7) | 0.00087 (5) | −0.00065 (5) | −0.00112 (5) |
O1 | 0.0075 (6) | 0.0288 (8) | 0.0121 (7) | 0.0020 (6) | −0.0015 (5) | −0.0006 (6) |
O2 | 0.0108 (7) | 0.0300 (9) | 0.0132 (7) | 0.0026 (6) | 0.0004 (6) | −0.0029 (6) |
O3 | 0.0100 (7) | 0.0330 (9) | 0.0103 (7) | 0.0025 (6) | 0.0002 (5) | −0.0025 (6) |
O4 | 0.0116 (7) | 0.0340 (9) | 0.0150 (7) | 0.0052 (7) | 0.0033 (6) | −0.0020 (7) |
N1 | 0.0056 (7) | 0.0174 (8) | 0.0150 (8) | 0.0014 (7) | 0.0007 (6) | −0.0009 (7) |
N2 | 0.0063 (7) | 0.0129 (8) | 0.0127 (8) | 0.0002 (6) | −0.0006 (6) | −0.0008 (6) |
C1 | 0.0101 (9) | 0.0116 (9) | 0.0139 (9) | −0.0010 (7) | −0.0008 (7) | −0.0007 (7) |
C2 | 0.0099 (9) | 0.0135 (9) | 0.0143 (9) | −0.0008 (7) | 0.0004 (7) | −0.0007 (8) |
C3 | 0.0097 (9) | 0.0151 (10) | 0.0143 (9) | −0.0006 (7) | 0.0006 (7) | −0.0010 (8) |
C4 | 0.0110 (9) | 0.0159 (10) | 0.0165 (9) | −0.0034 (8) | 0.0023 (7) | −0.0013 (8) |
C5 | 0.0148 (10) | 0.0235 (11) | 0.0176 (10) | −0.0014 (9) | 0.0023 (8) | −0.0008 (9) |
C6 | 0.0190 (11) | 0.0272 (12) | 0.0199 (11) | −0.0043 (9) | 0.0086 (9) | −0.0036 (9) |
C7 | 0.0132 (10) | 0.0219 (11) | 0.0285 (12) | −0.0017 (9) | 0.0097 (9) | −0.0026 (9) |
C8 | 0.0093 (9) | 0.0189 (11) | 0.0244 (11) | 0.0006 (8) | 0.0020 (8) | −0.0018 (9) |
C9 | 0.0099 (9) | 0.0133 (9) | 0.0200 (10) | −0.0020 (8) | 0.0015 (8) | −0.0013 (8) |
C10 | 0.0094 (9) | 0.0166 (10) | 0.0170 (10) | −0.0003 (8) | −0.0019 (7) | −0.0021 (8) |
C11 | 0.0132 (9) | 0.0117 (10) | 0.0142 (9) | −0.0006 (7) | 0.0004 (7) | −0.0021 (7) |
C12 | 0.0101 (9) | 0.0124 (9) | 0.0126 (9) | −0.0014 (7) | −0.0001 (7) | −0.0002 (7) |
C13 | 0.0117 (9) | 0.0125 (9) | 0.0128 (9) | −0.0001 (7) | 0.0008 (7) | 0.0004 (7) |
C14 | 0.0114 (9) | 0.0142 (9) | 0.0129 (9) | −0.0006 (8) | 0.0005 (7) | −0.0012 (8) |
C15 | 0.0098 (9) | 0.0173 (10) | 0.0152 (9) | 0.0006 (8) | 0.0013 (7) | −0.0004 (8) |
C16 | 0.0126 (9) | 0.0146 (10) | 0.0168 (10) | 0.0011 (8) | 0.0050 (8) | −0.0008 (8) |
C17 | 0.0143 (10) | 0.0237 (11) | 0.0131 (9) | 0.0004 (8) | 0.0010 (8) | −0.0010 (8) |
C18 | 0.0121 (9) | 0.0198 (10) | 0.0128 (9) | 0.0012 (8) | −0.0004 (7) | 0.0012 (8) |
C19 | 0.0107 (9) | 0.0188 (10) | 0.0158 (9) | 0.0023 (8) | 0.0027 (7) | −0.0007 (8) |
C20 | 0.0138 (10) | 0.0176 (10) | 0.0145 (9) | 0.0010 (8) | 0.0038 (8) | 0.0017 (8) |
C21 | 0.0115 (9) | 0.0198 (10) | 0.0171 (10) | 0.0011 (8) | 0.0037 (8) | 0.0000 (8) |
C22 | 0.0134 (10) | 0.0167 (10) | 0.0179 (10) | 0.0005 (8) | 0.0043 (8) | 0.0006 (8) |
C23 | 0.0117 (9) | 0.0187 (10) | 0.0163 (9) | 0.0008 (8) | 0.0031 (8) | 0.0019 (8) |
C24 | 0.0122 (9) | 0.0168 (10) | 0.0163 (9) | 0.0003 (8) | 0.0025 (8) | −0.0009 (8) |
C25 | 0.0136 (10) | 0.0197 (10) | 0.0171 (10) | 0.0032 (8) | 0.0037 (8) | 0.0021 (9) |
C26 | 0.0127 (9) | 0.0175 (10) | 0.0151 (9) | 0.0025 (8) | 0.0034 (8) | −0.0012 (8) |
C27 | 0.0141 (10) | 0.0213 (11) | 0.0172 (10) | 0.0039 (8) | 0.0045 (8) | −0.0008 (8) |
C28 | 0.0165 (11) | 0.0272 (12) | 0.0193 (10) | 0.0053 (9) | 0.0056 (8) | −0.0006 (9) |
C29 | 0.0209 (11) | 0.0200 (11) | 0.0186 (10) | 0.0062 (9) | 0.0036 (8) | 0.0030 (9) |
C30 | 0.0171 (10) | 0.0190 (11) | 0.0222 (11) | −0.0015 (9) | 0.0010 (8) | −0.0036 (9) |
Sn—O1 | 2.1600 (15) | C17—C18 | 1.361 (3) |
Sn—O3 | 2.0984 (15) | C17—H17 | 0.9500 |
Sn—N2 | 2.1503 (16) | C18—H18 | 0.9500 |
Sn—C29 | 2.112 (2) | C19—C20 | 1.517 (3) |
Sn—C30 | 2.106 (2) | C19—H19A | 0.9900 |
O1—C1 | 1.295 (2) | C19—H19B | 0.9900 |
O2—C11 | 1.366 (2) | C20—C21 | 1.520 (3) |
O2—H2O | 0.833 (10) | C20—H20A | 0.9900 |
O3—C14 | 1.316 (2) | C20—H20B | 0.9900 |
O4—C16 | 1.351 (2) | C21—C22 | 1.532 (3) |
O4—C19 | 1.436 (2) | C21—H21A | 0.9900 |
N1—C1 | 1.317 (3) | C21—H21B | 0.9900 |
N1—N2 | 1.397 (2) | C22—C23 | 1.523 (3) |
N2—C12 | 1.303 (3) | C22—H22A | 0.9900 |
C1—C2 | 1.480 (3) | C22—H22B | 0.9900 |
C2—C3 | 1.381 (3) | C23—C24 | 1.527 (3) |
C2—C11 | 1.432 (3) | C23—H23A | 0.9900 |
C3—C4 | 1.412 (3) | C23—H23B | 0.9900 |
C3—H3 | 0.9500 | C24—C25 | 1.527 (3) |
C4—C9 | 1.422 (3) | C24—H24A | 0.9900 |
C4—C5 | 1.419 (3) | C24—H24B | 0.9900 |
C5—C6 | 1.367 (3) | C25—C26 | 1.524 (3) |
C5—H5 | 0.9500 | C25—H25A | 0.9900 |
C6—C7 | 1.414 (3) | C25—H25B | 0.9900 |
C6—H6 | 0.9500 | C26—C27 | 1.524 (3) |
C7—C8 | 1.368 (3) | C26—H26A | 0.9900 |
C7—H7 | 0.9500 | C26—H26B | 0.9900 |
C8—C9 | 1.424 (3) | C27—C28 | 1.521 (3) |
C8—H8 | 0.9500 | C27—H27A | 0.9900 |
C9—C10 | 1.414 (3) | C27—H27B | 0.9900 |
C10—C11 | 1.372 (3) | C28—H28A | 0.9800 |
C10—H10 | 0.9500 | C28—H28B | 0.9800 |
C12—C13 | 1.416 (3) | C28—H28C | 0.9800 |
C12—H12 | 0.9500 | C29—H29A | 0.9800 |
C13—C14 | 1.421 (3) | C29—H29B | 0.9800 |
C13—C18 | 1.418 (3) | C29—H29C | 0.9800 |
C14—C15 | 1.410 (3) | C30—H30A | 0.9800 |
C15—C16 | 1.385 (3) | C30—H30B | 0.9800 |
C15—H15 | 0.9500 | C30—H30C | 0.9800 |
C16—C17 | 1.409 (3) | ||
O1—Sn—O3 | 157.14 (6) | O4—C19—C20 | 102.98 (16) |
O1—Sn—N2 | 73.16 (6) | O4—C19—H19A | 111.2 |
O1—Sn—C30 | 94.86 (8) | C20—C19—H19A | 111.2 |
O1—Sn—C29 | 95.42 (8) | O4—C19—H19B | 111.2 |
O3—Sn—N2 | 84.04 (6) | C20—C19—H19B | 111.2 |
O3—Sn—C30 | 96.19 (8) | H19A—C19—H19B | 109.1 |
O3—Sn—C29 | 94.21 (8) | C19—C20—C21 | 117.36 (18) |
N2—Sn—C29 | 119.12 (8) | C19—C20—H20A | 108.0 |
N2—Sn—C30 | 114.72 (8) | C21—C20—H20A | 108.0 |
C29—Sn—C30 | 125.89 (9) | C19—C20—H20B | 108.0 |
C1—O1—Sn | 114.34 (13) | C21—C20—H20B | 108.0 |
C11—O2—H2O | 111 (2) | H20A—C20—H20B | 107.2 |
C14—O3—Sn | 133.15 (13) | C20—C21—C22 | 108.66 (17) |
C16—O4—C19 | 121.44 (16) | C20—C21—H21A | 110.0 |
C1—N1—N2 | 112.04 (16) | C22—C21—H21A | 110.0 |
C12—N2—N1 | 115.10 (16) | C20—C21—H21B | 110.0 |
C12—N2—Sn | 128.31 (14) | C22—C21—H21B | 110.0 |
N1—N2—Sn | 116.60 (12) | H21A—C21—H21B | 108.3 |
O1—C1—N1 | 123.67 (18) | C23—C22—C21 | 116.88 (17) |
O1—C1—C2 | 119.01 (17) | C23—C22—H22A | 108.1 |
N1—C1—C2 | 117.32 (17) | C21—C22—H22A | 108.1 |
C3—C2—C11 | 118.88 (18) | C23—C22—H22B | 108.1 |
C3—C2—C1 | 118.98 (18) | C21—C22—H22B | 108.1 |
C11—C2—C1 | 122.14 (18) | H22A—C22—H22B | 107.3 |
C2—C3—C4 | 121.77 (19) | C22—C23—C24 | 110.33 (17) |
C2—C3—H3 | 119.1 | C22—C23—H23A | 109.6 |
C4—C3—H3 | 119.1 | C24—C23—H23A | 109.6 |
C3—C4—C9 | 118.88 (19) | C22—C23—H23B | 109.6 |
C3—C4—C5 | 121.97 (19) | C24—C23—H23B | 109.6 |
C9—C4—C5 | 119.14 (19) | H23A—C23—H23B | 108.1 |
C6—C5—C4 | 120.9 (2) | C25—C24—C23 | 114.90 (17) |
C6—C5—H5 | 119.6 | C25—C24—H24A | 108.5 |
C4—C5—H5 | 119.6 | C23—C24—H24A | 108.5 |
C5—C6—C7 | 119.9 (2) | C25—C24—H24B | 108.5 |
C5—C6—H6 | 120.0 | C23—C24—H24B | 108.5 |
C7—C6—H6 | 120.0 | H24A—C24—H24B | 107.5 |
C8—C7—C6 | 121.0 (2) | C24—C25—C26 | 112.70 (17) |
C8—C7—H7 | 119.5 | C24—C25—H25A | 109.1 |
C6—C7—H7 | 119.5 | C26—C25—H25A | 109.1 |
C7—C8—C9 | 120.3 (2) | C24—C25—H25B | 109.1 |
C7—C8—H8 | 119.9 | C26—C25—H25B | 109.1 |
C9—C8—H8 | 119.9 | H25A—C25—H25B | 107.8 |
C4—C9—C10 | 118.93 (19) | C27—C26—C25 | 113.44 (17) |
C4—C9—C8 | 118.8 (2) | C27—C26—H26A | 108.9 |
C10—C9—C8 | 122.23 (19) | C25—C26—H26A | 108.9 |
C11—C10—C9 | 121.36 (19) | C27—C26—H26B | 108.9 |
C11—C10—H10 | 119.3 | C25—C26—H26B | 108.9 |
C9—C10—H10 | 119.3 | H26A—C26—H26B | 107.7 |
O2—C11—C10 | 118.09 (18) | C28—C27—C26 | 112.29 (18) |
O2—C11—C2 | 121.78 (18) | C28—C27—H27A | 109.1 |
C10—C11—C2 | 120.13 (18) | C26—C27—H27A | 109.1 |
N2—C12—C13 | 126.98 (18) | C28—C27—H27B | 109.1 |
N2—C12—H12 | 116.5 | C26—C27—H27B | 109.1 |
C13—C12—H12 | 116.5 | H27A—C27—H27B | 107.9 |
C14—C13—C12 | 124.92 (18) | C27—C28—H28A | 109.5 |
C14—C13—C18 | 119.19 (18) | C27—C28—H28B | 109.5 |
C12—C13—C18 | 115.89 (18) | H28A—C28—H28B | 109.5 |
O3—C14—C15 | 118.94 (18) | C27—C28—H28C | 109.5 |
O3—C14—C13 | 122.50 (18) | H28A—C28—H28C | 109.5 |
C15—C14—C13 | 118.57 (18) | H28B—C28—H28C | 109.5 |
C16—C15—C14 | 120.18 (19) | Sn—C29—H29A | 109.5 |
C16—C15—H15 | 119.9 | Sn—C29—H29B | 109.5 |
C14—C15—H15 | 119.9 | H29A—C29—H29B | 109.5 |
O4—C16—C15 | 125.36 (19) | Sn—C29—H29C | 109.5 |
O4—C16—C17 | 113.16 (18) | H29A—C29—H29C | 109.5 |
C15—C16—C17 | 121.48 (19) | H29B—C29—H29C | 109.5 |
C18—C17—C16 | 118.78 (19) | Sn—C30—H30A | 109.5 |
C18—C17—H17 | 120.6 | Sn—C30—H30B | 109.5 |
C16—C17—H17 | 120.6 | H30A—C30—H30B | 109.5 |
C17—C18—C13 | 121.79 (19) | Sn—C30—H30C | 109.5 |
C17—C18—H18 | 119.1 | H30A—C30—H30C | 109.5 |
C13—C18—H18 | 119.1 | H30B—C30—H30C | 109.5 |
C1—N1—N2—C12 | 176.40 (18) | C1—C2—C11—C10 | 178.0 (2) |
C1—N1—N2—Sn | −3.7 (2) | N1—N2—C12—C13 | 179.75 (19) |
Sn—O1—C1—N1 | 2.8 (3) | Sn—N2—C12—C13 | −0.2 (3) |
Sn—O1—C1—C2 | −177.56 (14) | N2—C12—C13—C14 | −1.6 (3) |
N2—N1—C1—O1 | 0.6 (3) | N2—C12—C13—C18 | 178.1 (2) |
N2—N1—C1—C2 | −179.12 (17) | Sn—O3—C14—C15 | −177.01 (15) |
O1—C1—C2—C3 | −0.8 (3) | Sn—O3—C14—C13 | 3.2 (3) |
N1—C1—C2—C3 | 178.86 (19) | C12—C13—C14—O3 | 0.2 (3) |
O1—C1—C2—C11 | 179.99 (19) | C18—C13—C14—O3 | −179.6 (2) |
N1—C1—C2—C11 | −0.3 (3) | C12—C13—C14—C15 | −179.6 (2) |
C11—C2—C3—C4 | 1.3 (3) | C18—C13—C14—C15 | 0.6 (3) |
C1—C2—C3—C4 | −177.91 (19) | O3—C14—C15—C16 | −179.0 (2) |
C2—C3—C4—C9 | 0.3 (3) | C13—C14—C15—C16 | 0.8 (3) |
C2—C3—C4—C5 | 179.7 (2) | C19—O4—C16—C15 | 4.8 (3) |
C3—C4—C5—C6 | −178.8 (2) | C19—O4—C16—C17 | −175.49 (19) |
C9—C4—C5—C6 | 0.7 (3) | C14—C15—C16—O4 | 178.2 (2) |
C4—C5—C6—C7 | 0.6 (4) | C14—C15—C16—C17 | −1.5 (3) |
C5—C6—C7—C8 | −1.1 (4) | O4—C16—C17—C18 | −178.9 (2) |
C6—C7—C8—C9 | 0.2 (3) | C15—C16—C17—C18 | 0.9 (3) |
C3—C4—C9—C10 | −2.0 (3) | C16—C17—C18—C13 | 0.5 (3) |
C5—C4—C9—C10 | 178.5 (2) | C14—C13—C18—C17 | −1.3 (3) |
C3—C4—C9—C8 | 178.0 (2) | C12—C13—C18—C17 | 178.9 (2) |
C5—C4—C9—C8 | −1.5 (3) | C16—O4—C19—C20 | 174.88 (18) |
C7—C8—C9—C4 | 1.0 (3) | O4—C19—C20—C21 | 176.30 (18) |
C7—C8—C9—C10 | −179.0 (2) | C19—C20—C21—C22 | −175.71 (18) |
C4—C9—C10—C11 | 2.2 (3) | C20—C21—C22—C23 | −179.36 (18) |
C8—C9—C10—C11 | −177.8 (2) | C21—C22—C23—C24 | −174.96 (18) |
C9—C10—C11—O2 | 179.35 (19) | C22—C23—C24—C25 | 179.63 (18) |
C9—C10—C11—C2 | −0.6 (3) | C23—C24—C25—C26 | −178.75 (18) |
C3—C2—C11—O2 | 178.89 (19) | C24—C25—C26—C27 | 176.35 (18) |
C1—C2—C11—O2 | −1.9 (3) | C25—C26—C27—C28 | 179.79 (19) |
C3—C2—C11—C10 | −1.2 (3) |
Cg1–Cg4 are the centroids of the (Sn,O1,N1,N2,C1), (Sn,O3,N2,C12–C14), (C2–C4,C9–C11) and (C4—C9) rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···N1 | 0.83 (2) | 1.86 (2) | 2.580 (2) | 145 (3) |
C12—H12···O2i | 0.95 | 2.52 | 3.386 (3) | 152 |
C22—H22A···Cg1ii | 0.99 | 2.86 | 3.782 (2) | 155 |
C20—H20B···Cg2ii | 0.99 | 2.76 | 3.650 (2) | 149 |
C24—H24B···Cg3iii | 0.99 | 2.74 | 3.609 (2) | 146 |
C26—H26B···Cg4iii | 0.99 | 2.78 | 3.696 (2) | 154 |
Symmetry codes: (i) −x+1/2, y, −z+1; (ii) x+3/2, y+1/2, z+3/2; (iii) x+3/2, y+3/2, z+3/2. |
Contact | % contribution |
H···H | 63.6 |
C···H/H···C | 20.9 |
O···H/H···O | 8.9 |
N···H/H···N | 3.6 |
C···C | 1.8 |
C···O/O···C | 1.1 |
O···O | 0.1 |
Contact | distance | symmetry operation |
H18···H25A | 2.38 | -1/2 + x, -y, z |
O2···H18 | 2.70 | 1/2 - x, y, 1 - z |
C10···H18 | 2.83 | 1/2 - x, y, 1 - z |
C18···H19A | 2.86 | 1 - x, -y, -1 + z |
Footnotes
‡Additional correspondence author, e-mail: annielee@sunway.edu.my.
Funding information
Funding for this research was provided by: Sunway Universitythe University of Malaya (award Nos. RP017B-14AFR, PG102–2015A); the Ministry of Higher Education of Malaysia (MOHE) Fundamental Research Grant Scheme (award No. No. FP033–2014B).
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