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κ2N,O)(isophthalato-κO)samarium(III) nitrate
of diaquatris(benzohydrazide-aDivision of Chemistry, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani, 12121, Thailand, bDepartment of Chemistry, Faculty of Science, Naresuan University, Muang, Phitsanulok, 65000, Thailand, and cMaterials and Textile Technology, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani, 12121, Thailand
*Correspondence e-mail: kc@tu.ac.th
The first benzohydrazide complex of a lanthanide is reported. In the title compound, [Sm(C8H4O4)(C7H8N2O)3(H2O)2]NO3, diaquatris(benzohydrazide-κ2N,O)(isophthalato-κO)samarium(III) nitrate, the SmIII ion is nine-coordinated in a distorted tricapped trigonal–prismatic geometry by three oxygen atoms and three nitrogen atoms from three benzhydrazide (bzz) ligands, one oxygen atom from the isophthalate (itp2−) ligand, and two oxygen atoms from coordinated water molecules. The nitrate group is disordered over two sets of sites with occupancy factors of 0.310 (17) and 0.690 (17). In the crystal, adjacent molecules are linked into chains via pairs of O—H⋯O and N—H⋯O hydrogen bonds between the carboxylate acceptor and the coordinated water and amine NH2 donors. Molecules are further stacked by π–π interactions involving the benzene ring of the itp2− ligands, forming double chains that extend in the b-axis direction. These double chains are further linked into a three-dimensional supramolecular network via hydrogen bonds (O—H⋯O, N—H⋯O and C—H⋯O) between the complex molecule and the nitrate groups along with C—H⋯π and π–π interactions involving the benzene rings of the bzz and itp2− ligands.
Keywords: crystal structure; hydrogen bonds; lanthanide; samarium(III).
CCDC reference: 1876239
1. Chemical context
Research on lanthanide-based coordination compounds is one of the most active fields in chemistry and materials science. Distinct from transition metal centers, lanthanide ions often demonstrate high and variable coordination numbers as well as diverse coordination geometries, which can lead to versatile structures and topologies (Cotton & Raithby, 2017). They are also very attractive luminescent centers for the high colour purity and relatively long lifetimes arising from electronic transitions within the partially filled 4f orbitals, which make them potential candidates for applications in lighting, photonics and as luminescent probes and sensors (Parker, 2000
; Bünzli & Piguet, 2005
; Cui et al., 2018
). Besides the metal ions, the organic ligands also have significant effects on the construction of novel lanthanide coordination compounds and their potential applications (Lu et al., 2012
; Xu et al., 2016
; You et al., 2018
). It is well-known that lanthanide ions have a high affinity for and prefer to bind to hard donor atoms such as oxygen-containing organic ligands, for instance aromatic carboxylic acids. Terephthalic acid and its derivatives have thus been widely employed in the synthesis of novel lanthanide-based coordination compounds with interesting architectures and properties (Karmakar et al., 2016
; Park & Oh, 2016
). These ligands can exhibit various coordination modes when coordinated to the metal centers, as well as serving as antennas or sensitizers to absorb light and transfer energy to the excited states of the central lanthanide ions (Bünzli & Piguet, 2005
). Aromatic organic compounds containing the hydrazide group have been used widely as chemical receptors for sensing anions (Ran et al., 2017
; Liu et al., 2018
), but have received less attention as metal chelators. In a search for new structural chemistry, we employed benzhydrazide (bzz) and isoterephthalic acid (H2itp) as ligands to react with Sm(NO3)3·6H2O under hydrothermal conditions, and the determination of the title compound is reported herein.
2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The comprises one SmIII ion, three benzhydrazide (bzz) ligands, one completely deprotonated isophthalate (itp2−) ligand, two coordinated water molecules, and one disordered NO3− ion. The hydrazide group of the bzz ligand adopts a bidentate μ2-η1:η1 chelating coordination mode, whereas the carboxylate groups of the fully deprotonated itp2− ligand display a μ1-η1:η0 monodentate coordination fashion. The SmIII ion is nine-coordinated by three oxygen atoms (O1, O2, O3) and three nitrogen atoms (N1, N3, N5) of three different bzz ligands, one oxygen atom (O4) from the completely deprotonated itp2− ligand, and other two oxygen atoms (O8, O9) from the coordinated water molecules. The central metal SmIII atom can be described as having a distorted tricapped trigonal–prismatic geometry, Fig. 2
, with the Sm—N and the Sm—O bond lengths in the ligand ranging from 2.633 (2) to 2.694 (2) Å and 2.340 (2) to 2.478 (2) Å, respectively, and the N/O—Sm—N/O bond angles fall in the range 60.97 (6) to 145.24 (6)°. These values are comparable to other reported values for oxygen/nitrogen-coordinated SmIII complexes (Alipour et al., 2016
; An et al., 2016
).
![]() | Figure 1 Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 2 View of the distorted tricapped trigonal–prismatic coordination geometry of the central SmIII atom. |
3. Supramolecular features
As can be seen in Fig. 3, one carboxylate group of the itp2− ligand adopts a monodentate coordination mode to the SmIII ion, while the other acts as an acceptor of hydrogen-bonding interactions (Table 1
) involving the water molecules and the amine NH2 group of the bzz ligand of an adjacent complex molecules. This arrangement gives rise to chains extending along the b-axis direction by offset π–π interactions between the benzene rings of symmetry-related itp2− ligands, Fig. 4
, with a centroid to centroid distance of Cg4⋯Cg4i = 3.692 (2) Å and a dihedral angle = 0.0 (2)° [Cg4 is the centroid of the C23–C29 ring; symmetry code: (i) 2 − x, 1 − y, 1 − z). Fig. 5
shows the crystal packing of the title compound along the a axis. The three-dimensional supramolecular architecture of the crystal is sustained by numerous O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds between the complex molecules and the nitrate groups along with weak C—H⋯π interactions between the aromatic C—H bonds and the benzene rings of the bzz ligands, Table 1
. Furthermore, weak aromatic π–π stacking interactions involving the bzz ligands [Cg1⋯Cg1ii = 3.882 (2) Å, dihedral angle = 0.0 (5)°; Cg1 is the centroid of the C2–C7 ring; symmetry code: (ii) 1 − x, −y, 2 − z;] , and the bzz and itp2− ligands [Cg2⋯Cg4iii = 3.715 (3) Å, dihedral angle = 4.7 (9)°; Cg2 is the centroid of the C9–C14 ring; symmetry code: (iii) 1 − x, 1 − y, 1 − z], are also observed, which help further to stabilize the crystal structure.
|
![]() | Figure 3 View of a supramolecular chain formed by O—H⋯O and N—H⋯O hydrogen bonds. |
![]() | Figure 4 View of a supramolecular double chain sustained by O—H⋯O and N—H⋯O hydrogen bonding along with π–π stacking interactions. |
![]() | Figure 5 The crystal packing of the title compound, viewed along the a axis. The nitrate molecules are shown with a space-filling model. |
4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.39, last update August 2018; Groom et al., 2016) gave 20 hits for the benzohydrazide complexes with transition metal ions, but none of them involves a lanthanide ion. The most typical coordination mode of benzohydrazide ligands in structures appears to be a bidentate chelating mode with metal centers through nitrogen and oxygen donor atoms (BOHYCU, Nyburg et al., 1971
; EKAMIM, Odunola et al., 2003
; EZARED, EZARIH, Patel et al., 2011
; XUQYUD01, Thiam et al., 2009
). In these complexes, the nitrogen atoms of the hydrazide group serve as donors for hydrogen bonding.
5. Synthesis and crystallization
A mixture of Sm(NO3)3·6H2O (44.5 mg, 0.1 mmol), bzz (27.4 mg, 0.2 mmol), H2itp (16.5 mg, 0.1 mmol), and H2O (4 ml) was sealed in a 15 ml Teflon-lined steel autoclave and heated at 373 K for 24 h. The mixture was cooled to room temperature and light-yellow block-shaped crystals of the title compound were obtained in 79% yield (35.2 mg, based on SmIII source). Analysis calculated (%) for C29H32N7O12Sm (1376.80): C 42.43; H 3.93; N 11.94%. Found: C 42.46; H 3.96; N 11.90%.
6. Refinement
Crystal data, data collection and structure . All H atoms were located in difference maps. The H atoms bonded to C atoms were treated as riding atoms in geometrically idealized position with C—H distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). The H atoms bonded to O and N atoms were located in a difference-Fourier map, but were refined with distance restraints of O—H = 0.84 ± 0.01 Å and N—H = 0.88 ± 0.01 Å, and with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(N). The nitrate group is disordered over two sets of sites, with occupancy factors of 0.310 (17) and 0.690 (17).
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Supporting information
CCDC reference: 1876239
https://doi.org/10.1107/S2056989018015360/pj2059sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018015360/pj2059Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989018015360/pj2059Isup3.cdx
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[Sm(C8H4O4)(C7H8N2O)3(H2O)2]NO3 | Z = 2 |
Mr = 820.96 | F(000) = 826 |
Triclinic, P1 | Dx = 1.645 Mg m−3 |
a = 11.0784 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.2518 (13) Å | Cell parameters from 9800 reflections |
c = 15.3590 (18) Å | θ = 3.1–27.3° |
α = 84.039 (4)° | µ = 1.84 mm−1 |
β = 78.487 (4)° | T = 296 K |
γ = 62.042 (3)° | Block, light yellow |
V = 1656.9 (3) Å3 | 0.22 × 0.2 × 0.2 mm |
Bruker D8 QUEST CMOS diffractometer | 7637 independent reflections |
Radiation source: microfocus sealed x-ray tube, Incoatec Iµus | 6577 reflections with I > 2σ(I) |
GraphiteDouble Bounce Multilayer Mirror monochromator | Rint = 0.056 |
Detector resolution: 10.5 pixels mm-1 | θmax = 27.6°, θmin = 3.1° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→14 |
Tmin = 0.698, Tmax = 0.746 | l = −19→20 |
52341 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.053 | w = 1/[σ2(Fo2) + (0.0209P)2 + 0.7036P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
7637 reflections | Δρmax = 0.47 e Å−3 |
531 parameters | Δρmin = −0.36 e Å−3 |
55 restraints |
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 | Occ. (<1) | |
Sm1 | 0.64247 (2) | 0.20819 (2) | 0.60370 (2) | 0.02461 (4) | |
O1 | 0.68088 (19) | 0.03820 (18) | 0.72193 (12) | 0.0396 (4) | |
O2 | 0.41572 (18) | 0.28637 (17) | 0.69227 (12) | 0.0384 (4) | |
O3 | 0.67732 (18) | 0.29498 (17) | 0.73343 (12) | 0.0368 (4) | |
O4 | 0.74767 (17) | 0.32614 (15) | 0.50425 (11) | 0.0320 (4) | |
O5 | 0.93740 (19) | 0.16420 (17) | 0.43030 (15) | 0.0507 (5) | |
O6 | 0.69780 (16) | 0.79297 (15) | 0.48404 (12) | 0.0337 (4) | |
O7 | 0.88238 (19) | 0.81877 (17) | 0.42352 (14) | 0.0466 (5) | |
O8 | 0.7757 (2) | 0.05576 (18) | 0.48831 (14) | 0.0409 (5) | |
H8A | 0.799 (3) | −0.0206 (17) | 0.470 (2) | 0.069 (11)* | |
H8B | 0.836 (3) | 0.079 (3) | 0.465 (2) | 0.075 (12)* | |
O9 | 0.50028 (18) | 0.28060 (17) | 0.48404 (12) | 0.0316 (4) | |
H9A | 0.548 (2) | 0.243 (3) | 0.4371 (11) | 0.036 (8)* | |
H9B | 0.431 (2) | 0.267 (3) | 0.493 (2) | 0.055 (10)* | |
O10A | 0.1374 (12) | 0.878 (2) | 0.7680 (9) | 0.066 (5) | 0.310 (17) |
O10B | 0.1940 (8) | 0.8003 (8) | 0.7345 (4) | 0.0735 (19) | 0.690 (17) |
O11A | 0.266 (2) | 0.9732 (16) | 0.7463 (14) | 0.088 (5) | 0.310 (17) |
O11B | 0.2010 (9) | 0.9791 (7) | 0.7585 (5) | 0.079 (2) | 0.690 (17) |
O12A | 0.357 (2) | 0.7680 (15) | 0.7052 (12) | 0.076 (5) | 0.310 (17) |
O12B | 0.3861 (6) | 0.8098 (8) | 0.6970 (5) | 0.0613 (16) | 0.690 (17) |
N1 | 0.5415 (2) | 0.0317 (2) | 0.60532 (14) | 0.0312 (5) | |
H1A | 0.589 (2) | −0.0320 (19) | 0.5659 (13) | 0.036 (8)* | |
H1B | 0.4578 (15) | 0.074 (3) | 0.5919 (19) | 0.048 (9)* | |
N2 | 0.5377 (2) | −0.0322 (2) | 0.68934 (14) | 0.0347 (5) | |
H2 | 0.487 (2) | −0.073 (2) | 0.7027 (18) | 0.042 (8)* | |
N3 | 0.4835 (2) | 0.4741 (2) | 0.62389 (15) | 0.0358 (5) | |
H3A | 0.534 (3) | 0.503 (3) | 0.6428 (18) | 0.047 (9)* | |
H3B | 0.448 (3) | 0.520 (3) | 0.5775 (14) | 0.062 (10)* | |
N4 | 0.3651 (2) | 0.5034 (2) | 0.68984 (14) | 0.0331 (5) | |
H4 | 0.313 (3) | 0.5874 (13) | 0.7034 (19) | 0.050 (9)* | |
N5 | 0.8956 (2) | 0.1034 (2) | 0.63928 (15) | 0.0318 (5) | |
H5A | 0.930 (3) | 0.0158 (11) | 0.6346 (18) | 0.040 (8)* | |
H5B | 0.949 (2) | 0.131 (3) | 0.6035 (15) | 0.037 (8)* | |
N6 | 0.8946 (2) | 0.1288 (2) | 0.72747 (15) | 0.0356 (5) | |
H6 | 0.9703 (18) | 0.084 (2) | 0.7502 (17) | 0.044 (8)* | |
N7A | 0.2522 (11) | 0.8721 (11) | 0.7372 (13) | 0.032 (4) | 0.310 (17) |
N7B | 0.2615 (8) | 0.8629 (9) | 0.7303 (8) | 0.056 (2) | 0.690 (17) |
C1 | 0.6114 (3) | −0.0239 (2) | 0.74407 (17) | 0.0325 (6) | |
C2 | 0.6105 (3) | −0.0903 (3) | 0.83308 (18) | 0.0368 (6) | |
C3 | 0.5432 (4) | −0.1672 (4) | 0.8608 (2) | 0.0667 (10) | |
H3 | 0.495609 | −0.181394 | 0.822857 | 0.080* | |
C4 | 0.5465 (5) | −0.2234 (4) | 0.9454 (3) | 0.0846 (13) | |
H4A | 0.500847 | −0.275456 | 0.963900 | 0.101* | |
C5 | 0.6148 (4) | −0.2039 (4) | 1.0014 (2) | 0.0693 (10) | |
H5 | 0.616239 | −0.242175 | 1.058118 | 0.083* | |
C6 | 0.6809 (4) | −0.1287 (4) | 0.9749 (2) | 0.0681 (10) | |
H6A | 0.728290 | −0.115280 | 1.013370 | 0.082* | |
C7 | 0.6789 (4) | −0.0715 (3) | 0.8912 (2) | 0.0563 (8) | |
H7 | 0.724585 | −0.019298 | 0.873923 | 0.068* | |
C8 | 0.3369 (2) | 0.4028 (3) | 0.71862 (16) | 0.0310 (5) | |
C9 | 0.2075 (3) | 0.4315 (3) | 0.78336 (17) | 0.0409 (7) | |
C10 | 0.1151 (3) | 0.5588 (4) | 0.8150 (2) | 0.0631 (9) | |
H10 | 0.133562 | 0.630937 | 0.796580 | 0.076* | |
C11 | −0.0048 (4) | 0.5792 (6) | 0.8740 (3) | 0.0937 (15) | |
H11 | −0.066925 | 0.665074 | 0.895052 | 0.112* | |
C12 | −0.0318 (5) | 0.4751 (7) | 0.9009 (3) | 0.0989 (17) | |
H12 | −0.112158 | 0.489572 | 0.941059 | 0.119* | |
C13 | 0.0568 (4) | 0.3492 (6) | 0.8701 (3) | 0.0827 (13) | |
H13 | 0.036416 | 0.278359 | 0.888977 | 0.099* | |
C14 | 0.1782 (3) | 0.3254 (4) | 0.8102 (2) | 0.0588 (9) | |
H14 | 0.238632 | 0.239352 | 0.788698 | 0.071* | |
C15 | 0.7799 (3) | 0.2250 (2) | 0.77007 (17) | 0.0335 (6) | |
C16 | 0.7760 (3) | 0.2465 (3) | 0.86489 (18) | 0.0394 (6) | |
C17 | 0.8465 (4) | 0.1409 (4) | 0.9196 (2) | 0.0587 (9) | |
H17 | 0.901844 | 0.054955 | 0.896659 | 0.070* | |
C18 | 0.8347 (4) | 0.1631 (5) | 1.0086 (3) | 0.0787 (12) | |
H18 | 0.881011 | 0.091693 | 1.045469 | 0.094* | |
C19 | 0.7552 (4) | 0.2898 (5) | 1.0424 (3) | 0.0776 (12) | |
H19 | 0.748237 | 0.304574 | 1.102061 | 0.093* | |
C20 | 0.6865 (4) | 0.3939 (4) | 0.9889 (2) | 0.0665 (10) | |
H20 | 0.633608 | 0.480011 | 1.012134 | 0.080* | |
C21 | 0.6941 (3) | 0.3734 (3) | 0.9001 (2) | 0.0529 (8) | |
H21 | 0.644298 | 0.444845 | 0.864386 | 0.064* | |
C22 | 0.8656 (2) | 0.2830 (2) | 0.45328 (16) | 0.0280 (5) | |
C23 | 0.9215 (2) | 0.3801 (2) | 0.42054 (15) | 0.0243 (5) | |
C24 | 0.8477 (2) | 0.5137 (2) | 0.44522 (15) | 0.0233 (5) | |
H24 | 0.761853 | 0.543431 | 0.482257 | 0.028* | |
C25 | 0.9000 (2) | 0.6041 (2) | 0.41547 (15) | 0.0239 (5) | |
C26 | 0.8210 (2) | 0.7487 (2) | 0.44296 (16) | 0.0275 (5) | |
C27 | 1.0285 (3) | 0.5579 (2) | 0.36103 (17) | 0.0336 (6) | |
H27 | 1.064915 | 0.617294 | 0.341062 | 0.040* | |
C28 | 1.1032 (3) | 0.4249 (3) | 0.33605 (19) | 0.0398 (6) | |
H28 | 1.189294 | 0.395113 | 0.299318 | 0.048* | |
C29 | 1.0498 (2) | 0.3361 (2) | 0.36574 (17) | 0.0331 (6) | |
H29 | 1.100071 | 0.246465 | 0.348907 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sm1 | 0.02326 (7) | 0.01824 (6) | 0.03323 (7) | −0.01103 (5) | −0.00329 (5) | 0.00044 (4) |
O1 | 0.0417 (10) | 0.0396 (10) | 0.0507 (11) | −0.0292 (9) | −0.0171 (9) | 0.0155 (9) |
O2 | 0.0333 (10) | 0.0308 (10) | 0.0500 (11) | −0.0170 (8) | 0.0014 (8) | −0.0011 (8) |
O3 | 0.0314 (10) | 0.0306 (9) | 0.0443 (11) | −0.0085 (8) | −0.0096 (8) | −0.0066 (8) |
O4 | 0.0293 (9) | 0.0208 (8) | 0.0441 (10) | −0.0136 (7) | 0.0044 (8) | −0.0035 (7) |
O5 | 0.0391 (11) | 0.0220 (9) | 0.0847 (15) | −0.0165 (8) | 0.0179 (10) | −0.0171 (9) |
O6 | 0.0241 (9) | 0.0201 (8) | 0.0562 (11) | −0.0096 (7) | −0.0036 (8) | −0.0069 (8) |
O7 | 0.0390 (10) | 0.0245 (9) | 0.0792 (14) | −0.0221 (8) | 0.0088 (10) | −0.0119 (9) |
O8 | 0.0371 (10) | 0.0243 (10) | 0.0609 (13) | −0.0182 (9) | 0.0106 (9) | −0.0149 (9) |
O9 | 0.0272 (10) | 0.0291 (9) | 0.0395 (11) | −0.0144 (8) | −0.0041 (8) | −0.0002 (8) |
O10A | 0.034 (5) | 0.093 (11) | 0.072 (7) | −0.031 (6) | −0.010 (4) | 0.008 (7) |
O10B | 0.058 (3) | 0.078 (4) | 0.100 (4) | −0.048 (3) | 0.002 (3) | −0.017 (3) |
O11A | 0.071 (10) | 0.050 (6) | 0.152 (12) | −0.030 (7) | −0.025 (9) | −0.011 (6) |
O11B | 0.079 (5) | 0.052 (3) | 0.103 (4) | −0.020 (3) | −0.028 (4) | −0.016 (2) |
O12A | 0.058 (8) | 0.051 (7) | 0.078 (7) | 0.014 (5) | −0.016 (6) | −0.020 (6) |
O12B | 0.047 (2) | 0.084 (4) | 0.058 (3) | −0.034 (2) | −0.0040 (18) | −0.014 (3) |
N1 | 0.0333 (12) | 0.0280 (11) | 0.0354 (12) | −0.0163 (10) | −0.0081 (10) | 0.0026 (9) |
N2 | 0.0415 (13) | 0.0336 (12) | 0.0398 (12) | −0.0271 (11) | −0.0086 (10) | 0.0078 (10) |
N3 | 0.0352 (13) | 0.0315 (12) | 0.0379 (13) | −0.0162 (10) | 0.0008 (10) | 0.0016 (10) |
N4 | 0.0304 (11) | 0.0271 (11) | 0.0343 (12) | −0.0093 (10) | 0.0023 (9) | −0.0047 (9) |
N5 | 0.0268 (11) | 0.0254 (11) | 0.0417 (13) | −0.0120 (9) | −0.0010 (10) | −0.0031 (10) |
N6 | 0.0268 (11) | 0.0359 (12) | 0.0439 (13) | −0.0126 (10) | −0.0095 (10) | −0.0014 (10) |
N7A | 0.018 (5) | 0.027 (6) | 0.038 (9) | 0.000 (4) | −0.017 (5) | 0.018 (5) |
N7B | 0.066 (5) | 0.072 (5) | 0.046 (5) | −0.044 (4) | −0.007 (4) | −0.005 (4) |
C1 | 0.0306 (13) | 0.0241 (12) | 0.0408 (15) | −0.0122 (11) | −0.0054 (11) | 0.0041 (11) |
C2 | 0.0374 (14) | 0.0297 (13) | 0.0412 (15) | −0.0150 (12) | −0.0072 (12) | 0.0067 (11) |
C3 | 0.088 (3) | 0.081 (3) | 0.064 (2) | −0.065 (2) | −0.033 (2) | 0.0345 (19) |
C4 | 0.104 (3) | 0.103 (3) | 0.078 (3) | −0.077 (3) | −0.032 (3) | 0.050 (2) |
C5 | 0.078 (3) | 0.071 (2) | 0.050 (2) | −0.030 (2) | −0.0131 (19) | 0.0227 (18) |
C6 | 0.086 (3) | 0.074 (2) | 0.051 (2) | −0.040 (2) | −0.0280 (19) | 0.0132 (18) |
C7 | 0.072 (2) | 0.061 (2) | 0.0528 (19) | −0.0429 (19) | −0.0210 (17) | 0.0143 (16) |
C8 | 0.0278 (13) | 0.0377 (14) | 0.0286 (13) | −0.0150 (11) | −0.0084 (10) | 0.0012 (11) |
C9 | 0.0301 (14) | 0.0648 (19) | 0.0301 (14) | −0.0244 (14) | −0.0032 (11) | −0.0007 (13) |
C10 | 0.0447 (18) | 0.083 (3) | 0.051 (2) | −0.0249 (18) | 0.0114 (15) | −0.0221 (18) |
C11 | 0.054 (2) | 0.134 (4) | 0.074 (3) | −0.035 (3) | 0.026 (2) | −0.038 (3) |
C12 | 0.060 (3) | 0.179 (6) | 0.059 (3) | −0.064 (3) | 0.017 (2) | −0.014 (3) |
C13 | 0.075 (3) | 0.144 (4) | 0.059 (2) | −0.080 (3) | −0.007 (2) | 0.021 (3) |
C14 | 0.0502 (19) | 0.087 (3) | 0.0506 (19) | −0.0439 (19) | −0.0074 (15) | 0.0128 (18) |
C15 | 0.0331 (14) | 0.0297 (13) | 0.0428 (15) | −0.0184 (12) | −0.0061 (12) | −0.0020 (11) |
C16 | 0.0355 (14) | 0.0465 (16) | 0.0438 (16) | −0.0234 (13) | −0.0098 (12) | −0.0026 (13) |
C17 | 0.057 (2) | 0.064 (2) | 0.055 (2) | −0.0227 (17) | −0.0228 (17) | −0.0007 (17) |
C18 | 0.078 (3) | 0.099 (3) | 0.059 (2) | −0.033 (2) | −0.035 (2) | 0.008 (2) |
C19 | 0.076 (3) | 0.120 (4) | 0.051 (2) | −0.053 (3) | −0.017 (2) | −0.012 (2) |
C20 | 0.073 (2) | 0.078 (3) | 0.056 (2) | −0.041 (2) | 0.0006 (19) | −0.0246 (19) |
C21 | 0.0538 (19) | 0.0540 (19) | 0.0530 (19) | −0.0261 (16) | −0.0056 (15) | −0.0091 (15) |
C22 | 0.0292 (13) | 0.0189 (11) | 0.0365 (14) | −0.0116 (10) | −0.0051 (11) | −0.0014 (10) |
C23 | 0.0227 (11) | 0.0205 (11) | 0.0303 (12) | −0.0105 (9) | −0.0044 (10) | 0.0005 (9) |
C24 | 0.0215 (11) | 0.0209 (11) | 0.0283 (12) | −0.0106 (9) | −0.0039 (9) | −0.0006 (9) |
C25 | 0.0238 (11) | 0.0197 (11) | 0.0314 (12) | −0.0117 (9) | −0.0075 (10) | 0.0002 (9) |
C26 | 0.0268 (12) | 0.0204 (11) | 0.0382 (14) | −0.0123 (10) | −0.0081 (11) | −0.0005 (10) |
C27 | 0.0320 (13) | 0.0282 (13) | 0.0448 (15) | −0.0201 (11) | 0.0016 (11) | −0.0016 (11) |
C28 | 0.0286 (13) | 0.0324 (14) | 0.0534 (17) | −0.0154 (11) | 0.0117 (12) | −0.0102 (12) |
C29 | 0.0290 (13) | 0.0210 (12) | 0.0448 (15) | −0.0099 (10) | 0.0032 (11) | −0.0087 (11) |
Sm1—O1 | 2.4415 (17) | C3—C4 | 1.385 (5) |
Sm1—O2 | 2.3973 (17) | C4—H4A | 0.9300 |
Sm1—O3 | 2.4775 (17) | C4—C5 | 1.348 (5) |
Sm1—O4 | 2.4024 (16) | C5—H5 | 0.9300 |
Sm1—O8 | 2.3397 (19) | C5—C6 | 1.344 (5) |
Sm1—O9 | 2.4827 (18) | C6—H6A | 0.9300 |
Sm1—N1 | 2.694 (2) | C6—C7 | 1.375 (4) |
Sm1—N3 | 2.680 (2) | C7—H7 | 0.9300 |
Sm1—N5 | 2.633 (2) | C8—C9 | 1.487 (3) |
O1—C1 | 1.243 (3) | C9—C10 | 1.381 (4) |
O2—C8 | 1.240 (3) | C9—C14 | 1.380 (4) |
O3—C15 | 1.246 (3) | C10—H10 | 0.9300 |
O4—C22 | 1.277 (3) | C10—C11 | 1.384 (5) |
O5—C22 | 1.238 (3) | C11—H11 | 0.9300 |
O6—C26 | 1.262 (3) | C11—C12 | 1.346 (7) |
O7—C26 | 1.244 (3) | C12—H12 | 0.9300 |
O8—H8A | 0.834 (10) | C12—C13 | 1.358 (7) |
O8—H8B | 0.837 (10) | C13—H13 | 0.9300 |
O9—H9A | 0.825 (10) | C13—C14 | 1.395 (5) |
O9—H9B | 0.831 (10) | C14—H14 | 0.9300 |
O10A—N7A | 1.238 (12) | C15—C16 | 1.490 (4) |
O10B—N7B | 1.234 (8) | C16—C17 | 1.383 (4) |
O11A—N7A | 1.242 (13) | C16—C21 | 1.380 (4) |
O11B—N7B | 1.235 (8) | C17—H17 | 0.9300 |
O12A—N7A | 1.257 (12) | C17—C18 | 1.384 (5) |
O12B—N7B | 1.238 (8) | C18—H18 | 0.9300 |
N1—H1A | 0.875 (10) | C18—C19 | 1.368 (6) |
N1—H1B | 0.878 (10) | C19—H19 | 0.9300 |
N1—N2 | 1.413 (3) | C19—C20 | 1.356 (5) |
N2—H2 | 0.871 (10) | C20—H20 | 0.9300 |
N2—C1 | 1.320 (3) | C20—C21 | 1.387 (5) |
N3—H3A | 0.870 (10) | C21—H21 | 0.9300 |
N3—H3B | 0.878 (10) | C22—C23 | 1.492 (3) |
N3—N4 | 1.410 (3) | C23—C24 | 1.384 (3) |
N4—H4 | 0.867 (10) | C23—C29 | 1.387 (3) |
N4—C8 | 1.322 (3) | C24—H24 | 0.9300 |
N5—H5A | 0.879 (10) | C24—C25 | 1.388 (3) |
N5—H5B | 0.871 (10) | C25—C26 | 1.501 (3) |
N5—N6 | 1.410 (3) | C25—C27 | 1.385 (3) |
N6—H6 | 0.873 (10) | C27—H27 | 0.9300 |
N6—C15 | 1.319 (3) | C27—C28 | 1.379 (3) |
C1—C2 | 1.489 (3) | C28—H28 | 0.9300 |
C2—C3 | 1.373 (4) | C28—C29 | 1.381 (3) |
C2—C7 | 1.370 (4) | C29—H29 | 0.9300 |
C3—H3 | 0.9300 | ||
O1—Sm1—O3 | 72.08 (6) | C7—C2—C1 | 117.9 (2) |
O1—Sm1—O9 | 133.85 (6) | C7—C2—C3 | 118.2 (3) |
O1—Sm1—N1 | 60.97 (6) | C2—C3—H3 | 120.1 |
O1—Sm1—N3 | 125.95 (7) | C2—C3—C4 | 119.8 (3) |
O1—Sm1—N5 | 67.85 (6) | C4—C3—H3 | 120.1 |
O2—Sm1—O1 | 77.69 (6) | C3—C4—H4A | 119.5 |
O2—Sm1—O3 | 79.96 (6) | C5—C4—C3 | 121.0 (3) |
O2—Sm1—O4 | 131.15 (6) | C5—C4—H4A | 119.5 |
O2—Sm1—O9 | 80.28 (6) | C4—C5—H5 | 120.2 |
O2—Sm1—N1 | 68.37 (6) | C6—C5—C4 | 119.6 (3) |
O2—Sm1—N3 | 61.71 (6) | C6—C5—H5 | 120.2 |
O2—Sm1—N5 | 134.49 (7) | C5—C6—H6A | 119.8 |
O3—Sm1—O9 | 141.80 (6) | C5—C6—C7 | 120.5 (3) |
O3—Sm1—N1 | 127.30 (6) | C7—C6—H6A | 119.8 |
O3—Sm1—N3 | 67.24 (7) | C2—C7—C6 | 120.9 (3) |
O3—Sm1—N5 | 62.03 (6) | C2—C7—H7 | 119.5 |
O4—Sm1—O1 | 144.08 (6) | C6—C7—H7 | 119.5 |
O4—Sm1—O3 | 90.56 (6) | O2—C8—N4 | 121.2 (2) |
O4—Sm1—O9 | 78.51 (6) | O2—C8—C9 | 120.1 (2) |
O4—Sm1—N1 | 141.91 (6) | N4—C8—C9 | 118.7 (2) |
O4—Sm1—N3 | 70.39 (6) | C10—C9—C8 | 122.9 (3) |
O4—Sm1—N5 | 76.25 (6) | C14—C9—C8 | 117.6 (3) |
O8—Sm1—O1 | 95.65 (7) | C14—C9—C10 | 119.5 (3) |
O8—Sm1—O2 | 137.16 (6) | C9—C10—H10 | 120.0 |
O8—Sm1—O3 | 138.72 (7) | C9—C10—C11 | 120.1 (4) |
O8—Sm1—O4 | 76.66 (6) | C11—C10—H10 | 120.0 |
O8—Sm1—O9 | 74.43 (7) | C10—C11—H11 | 119.9 |
O8—Sm1—N1 | 71.49 (7) | C12—C11—C10 | 120.2 (4) |
O8—Sm1—N3 | 138.35 (7) | C12—C11—H11 | 119.9 |
O8—Sm1—N5 | 76.77 (7) | C11—C12—H12 | 119.6 |
O9—Sm1—N1 | 73.31 (6) | C11—C12—C13 | 120.8 (4) |
O9—Sm1—N3 | 74.63 (7) | C13—C12—H12 | 119.6 |
O9—Sm1—N5 | 145.24 (6) | C12—C13—H13 | 119.8 |
N3—Sm1—N1 | 123.90 (7) | C12—C13—C14 | 120.4 (4) |
N5—Sm1—N1 | 115.01 (7) | C14—C13—H13 | 119.8 |
N5—Sm1—N3 | 117.67 (7) | C9—C14—C13 | 119.0 (4) |
C1—O1—Sm1 | 124.68 (16) | C9—C14—H14 | 120.5 |
C8—O2—Sm1 | 126.68 (16) | C13—C14—H14 | 120.5 |
C15—O3—Sm1 | 120.32 (16) | O3—C15—N6 | 121.8 (2) |
C22—O4—Sm1 | 130.94 (14) | O3—C15—C16 | 120.6 (2) |
Sm1—O8—H8A | 144 (2) | N6—C15—C16 | 117.5 (2) |
Sm1—O8—H8B | 104 (3) | C17—C16—C15 | 121.6 (3) |
H8A—O8—H8B | 109 (3) | C21—C16—C15 | 119.1 (3) |
Sm1—O9—H9A | 110.4 (19) | C21—C16—C17 | 119.2 (3) |
Sm1—O9—H9B | 117 (2) | C16—C17—H17 | 120.0 |
H9A—O9—H9B | 106 (3) | C16—C17—C18 | 120.1 (3) |
Sm1—N1—H1A | 114.3 (18) | C18—C17—H17 | 120.0 |
Sm1—N1—H1B | 109.2 (19) | C17—C18—H18 | 119.9 |
H1A—N1—H1B | 105 (3) | C19—C18—C17 | 120.2 (4) |
N2—N1—Sm1 | 111.02 (14) | C19—C18—H18 | 119.9 |
N2—N1—H1A | 107.0 (17) | C18—C19—H19 | 120.0 |
N2—N1—H1B | 110.1 (19) | C20—C19—C18 | 120.0 (4) |
N1—N2—H2 | 119.1 (18) | C20—C19—H19 | 120.0 |
C1—N2—N1 | 117.4 (2) | C19—C20—H20 | 119.6 |
C1—N2—H2 | 123.5 (18) | C19—C20—C21 | 120.7 (4) |
Sm1—N3—H3A | 106 (2) | C21—C20—H20 | 119.6 |
Sm1—N3—H3B | 116 (2) | C16—C21—C20 | 119.7 (3) |
H3A—N3—H3B | 113 (3) | C16—C21—H21 | 120.1 |
N4—N3—Sm1 | 111.54 (14) | C20—C21—H21 | 120.1 |
N4—N3—H3A | 107 (2) | O4—C22—C23 | 118.50 (19) |
N4—N3—H3B | 103 (2) | O5—C22—O4 | 123.6 (2) |
N3—N4—H4 | 116 (2) | O5—C22—C23 | 117.9 (2) |
C8—N4—N3 | 117.1 (2) | C24—C23—C22 | 120.8 (2) |
C8—N4—H4 | 126 (2) | C24—C23—C29 | 119.3 (2) |
Sm1—N5—H5A | 106.2 (18) | C29—C23—C22 | 119.9 (2) |
Sm1—N5—H5B | 113.6 (18) | C23—C24—H24 | 119.5 |
H5A—N5—H5B | 110 (2) | C23—C24—C25 | 120.9 (2) |
N6—N5—Sm1 | 111.50 (14) | C25—C24—H24 | 119.5 |
N6—N5—H5A | 107.1 (18) | C24—C25—C26 | 121.1 (2) |
N6—N5—H5B | 108.7 (18) | C27—C25—C24 | 118.8 (2) |
N5—N6—H6 | 119.2 (19) | C27—C25—C26 | 120.1 (2) |
C15—N6—N5 | 117.6 (2) | O6—C26—C25 | 119.4 (2) |
C15—N6—H6 | 123.1 (19) | O7—C26—O6 | 123.5 (2) |
O10A—N7A—O11A | 116.6 (12) | O7—C26—C25 | 117.1 (2) |
O10A—N7A—O12A | 124.6 (13) | C25—C27—H27 | 119.6 |
O11A—N7A—O12A | 118.5 (13) | C28—C27—C25 | 120.9 (2) |
O10B—N7B—O11B | 118.4 (7) | C28—C27—H27 | 119.6 |
O10B—N7B—O12B | 119.9 (7) | C27—C28—H28 | 120.1 |
O11B—N7B—O12B | 121.7 (7) | C27—C28—C29 | 119.8 (2) |
O1—C1—N2 | 120.8 (2) | C29—C28—H28 | 120.1 |
O1—C1—C2 | 120.2 (2) | C23—C29—H29 | 119.9 |
N2—C1—C2 | 119.0 (2) | C28—C29—C23 | 120.3 (2) |
C3—C2—C1 | 123.9 (3) | C28—C29—H29 | 119.9 |
Sm1—O1—C1—N2 | 20.2 (3) | C3—C2—C7—C6 | 0.4 (5) |
Sm1—O1—C1—C2 | −159.95 (17) | C3—C4—C5—C6 | 0.0 (7) |
Sm1—O2—C8—N4 | 8.8 (3) | C4—C5—C6—C7 | 0.2 (6) |
Sm1—O2—C8—C9 | −171.58 (16) | C5—C6—C7—C2 | −0.4 (6) |
Sm1—O3—C15—N6 | 24.0 (3) | C7—C2—C3—C4 | −0.3 (5) |
Sm1—O3—C15—C16 | −155.18 (18) | C8—C9—C10—C11 | 178.8 (3) |
Sm1—O4—C22—O5 | 17.8 (4) | C8—C9—C14—C13 | −179.2 (3) |
Sm1—O4—C22—C23 | −161.23 (15) | C9—C10—C11—C12 | 0.1 (6) |
Sm1—N1—N2—C1 | −16.1 (3) | C10—C9—C14—C13 | −1.1 (5) |
Sm1—N3—N4—C8 | −12.0 (3) | C10—C11—C12—C13 | −0.7 (7) |
Sm1—N5—N6—C15 | −17.1 (3) | C11—C12—C13—C14 | 0.4 (7) |
O1—C1—C2—C3 | −176.1 (3) | C12—C13—C14—C9 | 0.5 (6) |
O1—C1—C2—C7 | 5.1 (4) | C14—C9—C10—C11 | 0.8 (5) |
O2—C8—C9—C10 | −179.7 (3) | C15—C16—C17—C18 | −176.6 (3) |
O2—C8—C9—C14 | −1.7 (4) | C15—C16—C21—C20 | 178.2 (3) |
O3—C15—C16—C17 | 146.7 (3) | C16—C17—C18—C19 | −1.1 (6) |
O3—C15—C16—C21 | −29.8 (4) | C17—C16—C21—C20 | 1.6 (5) |
O4—C22—C23—C24 | 0.4 (3) | C17—C18—C19—C20 | 0.7 (6) |
O4—C22—C23—C29 | 179.4 (2) | C18—C19—C20—C21 | 0.9 (6) |
O5—C22—C23—C24 | −178.7 (2) | C19—C20—C21—C16 | −2.0 (5) |
O5—C22—C23—C29 | 0.4 (4) | C21—C16—C17—C18 | −0.1 (5) |
N1—N2—C1—O1 | 0.1 (4) | C22—C23—C24—C25 | 179.5 (2) |
N1—N2—C1—C2 | −179.8 (2) | C22—C23—C29—C28 | −179.2 (2) |
N2—C1—C2—C3 | 3.8 (4) | C23—C24—C25—C26 | −179.3 (2) |
N2—C1—C2—C7 | −175.0 (3) | C23—C24—C25—C27 | −0.6 (3) |
N3—N4—C8—O2 | 4.0 (4) | C24—C23—C29—C28 | −0.1 (4) |
N3—N4—C8—C9 | −175.7 (2) | C24—C25—C26—O6 | −9.3 (3) |
N4—C8—C9—C10 | 0.0 (4) | C24—C25—C26—O7 | 170.6 (2) |
N4—C8—C9—C14 | 178.0 (2) | C24—C25—C27—C28 | 0.5 (4) |
N5—N6—C15—O3 | −2.7 (4) | C25—C27—C28—C29 | −0.2 (4) |
N5—N6—C15—C16 | 176.5 (2) | C26—C25—C27—C28 | 179.2 (2) |
N6—C15—C16—C17 | −32.5 (4) | C27—C25—C26—O6 | 172.0 (2) |
N6—C15—C16—C21 | 151.0 (3) | C27—C25—C26—O7 | −8.1 (4) |
C1—C2—C3—C4 | −179.0 (3) | C27—C28—C29—C23 | 0.0 (4) |
C1—C2—C7—C6 | 179.3 (3) | C29—C23—C24—C25 | 0.4 (3) |
C2—C3—C4—C5 | 0.1 (7) |
Cg1 and Cg3 are the centroids of the C2–C7 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8A···O7i | 0.83 (2) | 1.75 (2) | 2.574 (2) | 168 (3) |
O8—H8B···O5 | 0.84 (2) | 1.76 (2) | 2.585 (3) | 166 (3) |
O9—H9A···O12Aii | 0.83 (2) | 2.22 (2) | 2.988 (2) | 156 (3) |
O9—H9A···O12Bii | 0.83 (2) | 2.09 (2) | 2.888 (2) | 162 (3) |
O9—H9B···O6ii | 0.83 (2) | 1.81 (2) | 2.633 (2) | 170 (3) |
N1—H1A···O6i | 0.88 (2) | 2.14 (2) | 3.012 (3) | 172 (2) |
N1—H1B···O6ii | 0.88 (2) | 2.14 (2) | 2.965 (3) | 156 (3) |
N2—H2···O11Ai | 0.87 (2) | 2.22 (3) | 2.936 (2) | 140 (2) |
N2—H2···O12Bi | 0.87 (2) | 2.10 (2) | 2.946 (3) | 164 (3) |
N3—H3B···O4ii | 0.88 (2) | 2.53 (2) | 3.344 (3) | 155 (3) |
N4—H4···O10B | 0.87 (2) | 2.18 (2) | 3.040 (3) | 176 (3) |
N4—H4···O12A | 0.87 (2) | 2.31 (3) | 2.970 (2) | 133 (3) |
N5—H5A···O5iii | 0.88 (2) | 2.07 (2) | 2.878 (3) | 152 (2) |
N5—H5B···O5 | 0.87 (2) | 2.67 (2) | 3.199 (3) | 120 (2) |
N5—H5B···O7iv | 0.87 (2) | 2.15 (2) | 2.940 (3) | 151 (2) |
N6—H6···O10Av | 0.87 (2) | 2.22 (3) | 2.961 (2) | 142 (2) |
N6—H6···O11Bv | 0.87 (2) | 2.28 (2) | 3.115 (3) | 159 (3) |
C10—H10···O10B | 0.93 | 2.36 | 3.282 (2) | 173 |
C11—H11···Cg1vi | 0.93 | 3.10 | 3.866 (2) | 137 |
C13—H13···Cg3vii | 0.93 | 3.02 | 3.712 (4) | 132 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) −x+2, −y+1, −z+1; (v) x+1, y−1, z; (vi) x−1, y+1, z; (vii) x−1, y, z. |
Funding information
The authors acknowledge financial support provided from the NRCT and administered by the Division of Research Administration at Thammasat University under grant No. 25/2560. This work was also partially supported by the Thailand Research Fund under grant No. RTA6180007.
References
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