research communications
5-Methyl-1,3-phenylene bis[5-(dimethylamino)naphthalene-1-sulfonate]:
and DFT calculationsaDepartment of Chemistry and Center of Excellent for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, bDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, cMaterials and Textile Technology, Faculty of Science, and Technology, Thammasart University, Pathum Thani 12120, Thailand, dCenter of Nanotechnology, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, and eSupramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
*Correspondence e-mail: fscibnw@ku.ac.th
The title compound, C31H30N2S2O6, possesses crystallographically imposed twofold symmetry with the two C atoms of the central benzene ring and the C atom of its methyl substituent lying on the twofold rotation axis. The two dansyl groups are twisted away from the plane of methylphenyl bridging unit in opposite directions. The three-dimensional arrangement in the crystal is mainly stabilized by weak hydrogen bonds between the sulfonyl oxygen atoms and the hydrogen atoms from the N-methyl groups. Stacking of the dansyl group is not observed. From the DFT calculations, the HOMO–LUMO energy gap was found to be 2.99 eV and indicates n→π* and π→π* transitions within the molecule.
CCDC reference: 1535824
1. Chemical context
Dansyl probes play important roles in many fields, including their use as industrial tracers and labelled biological tags (Tondi et al., 2005; Li et al., 2006; Liu et al., 2016). Dansyl derivatives have been employed to identify some diseases within cells and to detect DNA-duplex sequences. For example, modified that contain a dansyl fluorophore and (S)-2, 3-dihydroxy propyl linked to guanine residues result in an enhancement of the fluorescence. Such modified can be used to prepare and detect the sequence of fluorogenic probes in DNA (Suzuki et al., 2013). Cu-labelled dansyl molecules have been designed and synthesized as fluorescence probes for membrane tags on apoptosis cells. These compounds can also be used for PET imaging of the apoptosis in vivo (Han et al., 2016). Furthermore, the development of dansyl fluorogenic receptors for cations, anions and neutral molecules has attracted much attention because of their ability to turn fluorescence `on' or `off' through a number of mechanisms including ICT, PET and ET processes (Chen & Chen, 2005; Praveen et al., 2010; Dinake et al. 2012; Jeong et al. 2016). In this paper, we report the synthesis, molecular structure and crystal packing of 5-methyl-1,3-phenylene bis[5-(dimethylamino)naphthalene-1-sulfonate]. The results of DFT calculations on the molecule are also reported.
2. Structural commentary
The title compound crystallizes in the C2/c. The molecule lies on a crystallographic twofold axis running through atoms C1, C2 and C5 of the methylphenyl unit so that the comprises one half-molecule (Fig. 1). The hydrogen atoms of the C1 methyl group are therefore disordered over two equivalent positions. Intramolecular C14—H14—O3 hydrogen bonds enclose S(6) rings, Fig. 1. The molecular structure comprises two O-dansyl groups on either side of a bridging methylphenyl ring that is essentially planar. The S1—O1—C4—C3 torsion angle is 72.98 (16)° with the methylphenyl ring plane. The S1 sulfur atoms have distorted tetrahedral geometries, with an O2—S1—C6 bond angle of 109.18 (8)°. The two naphthalene units in each dansyl group are inclined to one another at an angle of 52.29 (6)°; however, no stacking of the naphthalene units is observed.
3. Supramolecular features
In the . C9—H9—O1 contacts form dimers enclosing R22(22) rings and generate chains of molecules along the c-axis direction, Fig. 2. C1—H1B—O3 and C16—H16C—O2 contacts further link the molecules into sheets in the ab plane, Fig. 3. These contacts combine to stack rows of molecules arranged in an obverse fashion along the a-axis direction, Fig. 4.
the supramolecular packing is dominated by weak C—H⋯O hydrogen bonds, Table 14. Computational study
The Density Functional Theory (DFT) calculations were performed at the CAM-B3LYP/6-311G (d,p) level as implemented in the GAUSSIAN09 program package (Frisch et al., 2009). The DFT structure optimization of the compound was performed starting from the X-ray geometry. The experimental values of the bond lengths and bond angles match reasonably well with the theoretical values in most cases. However, the lengths of bonds to O atoms involved in hydrogen bonding fit less well, Table 2. The important features such as conjugation and aromaticity are well illustrated by frontier molecular orbitals. The of the molecule is determined from the energy of the highest occupied molecular orbital (HOMO) and the is calculated from the energy of the lowest unoccupied molecular orbital (LUMO). The frontier molecular orbital energies, EHOMO and ELUMO are −8.24 and −5.25 eV, respectively. Insights into the kinetic stability and chemical reactivity of a molecule can be determined from the energy difference between the HOMO and LUMO orbitals, the so-called HOMO–LUMO energy gap. This gap was found here to be 2.99 eV. The HOMO–LUMO energy levels indicate n→π* and π→π* transitions and are shown in Fig. 5. The HOMO is mainly localized on the nitrogen atom of dimethylamine group as well as on the C=C segments of the naphthalene ring systems while the LUMO is located again on the dimethylamine substituent and also on the aromatic rings of the naphthalene systems. In Fig. 5, the negative and positive phases are represented by green and red colours, respectively.
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5. Database survey
There are many crystal structures of dansyl derivatives that are similar to the title compound. Two categories of crystal structures of dansyl derivatives are found. The first types are simple organic molecules that pack in the solid state through the many types of intermolecular interactions. For example, in 2-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl 5-(dimethylamino)naphthalene-1-sulfonate [CSD (Groom et al., 2016) refcode NUQDOU; Chainok et al., 2015), there are two dansyl units connecting to the amine and hydroxyl groups of a 2-aminophenol, while weak C—H⋯O hydrogen bonds stabilize the In N-cyclododecyl-5-(dimethylamino)naphthalene-1-sulfonamide (HODDOU; Fischer et al., 2008) a cyclododecylamine linked to the dansyl substituent adopts a U-shaped conformation, and the crystal packing is stabilized by N—H⋯O hydrogen bonds and C—H⋯π interactions between neighbouring molecules. In 8-quinolyl 5-(dimethylamino)naphthalene-1-sulfonate, (DUVFOQ; Xiao & Zhan, 2010) with an 8-hydroxyquinoline ring, C—H⋯O hydrogen bonds and π–π interactions between pairs of chains link adjacent molecules. In the of N-(2-aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide (BOVBOE; Zhang et al., 2009) a dansyl compound with a 2-aminoethyl group, layers are formed through N—H⋯N and weak C—H⋯O hydrogen bonds. In 5,5′-bis(dimethylamino)-N,N′-(3-methyl-3-azapentane-1,5-diyl)di(naphthalene-1-sulfonamide) (DABSEH; Horne et al., 2015), packing in the relies on N—H⋯O and C—H⋯O interactions.
Metal–dansyl complexes form the second class of common dansyl derivatives. The crystal structures of the di- and trinuclear gold(I) complexes [5-(dimethylamino)naphthalene-1-sulfonamido]bis(triphenylphosphine)digold (UZEJAL) and [5-(dimethylamino)naphthalene-1-sulfonamido]tris(triphenylphosphine)trigold perchlorate (UZEJEP) (Cho et al., 2011) display weak Au⋯Au interactions and C—H⋯π contacts within the molecule. The Pb2+ complex 26,28-dibutoxy-25,27-bis(N-dansylcarbamoylmethoxy)-5,11,17,23-tetrakis(1,1-dimethylethyl)calix[4]arene (NOJRAG; Buie et al., 2008), where the calix[4]arene bears two dansylcarboxamide groups, was found to be highly selective and sensitive for the recognition of and coordination to the Pb2+ ion.
6. Synthesis and crystallization
The title compound was synthesized by mixing 3,5-dihydroxytoluene (1.05 g, 8.46 mmol) and dansyl chloride (4.55g, 17 mmol) using potassium carbonate(2.34g, 17 mmol) as a base in acetonitrile solvent (40 ml). The reaction mixture was heated at 363 K and stirred under an N2 atmosphere for 24 h. The solvent was removed with a rotary evaporator. The residue was added to water (15 ml) and extracted with dichloromethane (3 × 25ml). The organic layer was dried with anhydrous Na2SO4 and the product was purified by using CH2Cl2 as the The dichloromethane was slowly evaporated to afford a green solid in 65% yield. Light-green block-like crystals were grown in chloroform at room temperature.
7. Refinement
Crystal data, data collection and structure . All H atoms on C were refined using a riding model with d(C—H) = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic and d(C—H) = 0.98 Å, Uiso(H) = 1.5Ueq(C) for methyl H atoms. As atom Cl lies on a twofold rotation axis, the H atoms of the Cl methyl group are disordered with occupancies fixed at 0.5.
details are summarized in Table 3Supporting information
CCDC reference: 1535824
https://doi.org/10.1107/S2056989019009058/sj5573sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019009058/sj5573Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019009058/sj5573Isup3.cml
Data collection: APEX CCD (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C31H30N2O6S2 | F(000) = 1240 |
Mr = 590.69 | Dx = 1.385 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.5072 (6) Å | Cell parameters from 8490 reflections |
b = 12.3504 (5) Å | θ = 3.0–26.4° |
c = 16.3017 (5) Å | µ = 0.24 mm−1 |
β = 114.868 (1)° | T = 296 K |
V = 2832.62 (18) Å3 | Block, light green |
Z = 4 | 0.44 × 0.44 × 0.4 mm |
Bruker D8 QUEST CMOS diffractometer | 2857 independent reflections |
Radiation source: sealed tube | 2437 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 26.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −19→19 |
Tmin = 0.710, Tmax = 0.745 | k = −15→15 |
18169 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0573P)2 + 1.5124P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2857 reflections | Δρmax = 0.23 e Å−3 |
190 parameters | Δρmin = −0.33 e Å−3 |
0 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) | |
S1 | 0.24891 (3) | 0.59066 (4) | 0.67336 (3) | 0.04868 (15) | |
O1 | 0.35036 (8) | 0.59425 (9) | 0.75828 (7) | 0.0458 (3) | |
O2 | 0.21860 (9) | 0.69851 (11) | 0.64561 (10) | 0.0632 (4) | |
O3 | 0.19426 (9) | 0.52398 (12) | 0.70474 (10) | 0.0675 (4) | |
N1 | 0.43181 (10) | 0.25203 (12) | 0.48853 (10) | 0.0535 (4) | |
C6 | 0.27383 (10) | 0.52632 (13) | 0.58976 (11) | 0.0424 (4) | |
C7 | 0.25296 (12) | 0.58335 (13) | 0.51133 (12) | 0.0483 (4) | |
H7 | 0.2260 | 0.6519 | 0.5041 | 0.058* | |
C8 | 0.27244 (12) | 0.53779 (15) | 0.44241 (12) | 0.0526 (4) | |
H8 | 0.2545 | 0.5739 | 0.3876 | 0.063* | |
C9 | 0.31748 (12) | 0.44083 (14) | 0.45540 (11) | 0.0473 (4) | |
H9 | 0.3316 | 0.4125 | 0.4096 | 0.057* | |
C10 | 0.34350 (10) | 0.38180 (12) | 0.53666 (10) | 0.0400 (3) | |
C11 | 0.39393 (11) | 0.28115 (13) | 0.55059 (11) | 0.0458 (4) | |
C12 | 0.40220 (13) | 0.21854 (14) | 0.62272 (14) | 0.0586 (5) | |
H12 | 0.4305 | 0.1507 | 0.6302 | 0.070* | |
C13 | 0.36883 (15) | 0.25495 (16) | 0.68541 (14) | 0.0644 (5) | |
H13 | 0.3740 | 0.2096 | 0.7328 | 0.077* | |
C14 | 0.32938 (13) | 0.35391 (15) | 0.67920 (12) | 0.0532 (4) | |
H14 | 0.3114 | 0.3778 | 0.7238 | 0.064* | |
C15 | 0.31559 (10) | 0.42115 (12) | 0.60409 (10) | 0.0405 (3) | |
C16 | 0.51087 (14) | 0.32132 (16) | 0.49436 (14) | 0.0616 (5) | |
H16A | 0.4915 | 0.3958 | 0.4888 | 0.092* | |
H16B | 0.5289 | 0.3032 | 0.4465 | 0.092* | |
H16C | 0.5640 | 0.3103 | 0.5516 | 0.092* | |
C17 | 0.45713 (16) | 0.13831 (16) | 0.48903 (16) | 0.0728 (6) | |
H17A | 0.5091 | 0.1212 | 0.5457 | 0.109* | |
H17B | 0.4755 | 0.1250 | 0.4406 | 0.109* | |
H17C | 0.4034 | 0.0939 | 0.4812 | 0.109* | |
C4 | 0.42508 (10) | 0.65401 (13) | 0.75150 (10) | 0.0400 (3) | |
C3 | 0.42371 (11) | 0.76504 (14) | 0.75244 (11) | 0.0459 (4) | |
H3 | 0.3723 | 0.8016 | 0.7547 | 0.055* | |
C2 | 0.5000 | 0.82262 (19) | 0.7500 | 0.0490 (5) | |
C5 | 0.5000 | 0.59523 (18) | 0.7500 | 0.0398 (5) | |
H5 | 0.5000 | 0.5199 | 0.7500 | 0.048* | |
C1 | 0.5000 | 0.9447 (2) | 0.7500 | 0.0765 (9) | |
H1A | 0.4591 | 0.9706 | 0.6908 | 0.115* | 0.5 |
H1B | 0.5635 | 0.9706 | 0.7663 | 0.115* | 0.5 |
H1C | 0.4774 | 0.9706 | 0.7929 | 0.115* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0324 (2) | 0.0582 (3) | 0.0573 (3) | −0.00268 (16) | 0.02067 (19) | −0.00729 (18) |
O1 | 0.0378 (6) | 0.0558 (7) | 0.0467 (6) | −0.0065 (5) | 0.0208 (5) | −0.0008 (5) |
O2 | 0.0455 (6) | 0.0600 (8) | 0.0765 (9) | 0.0133 (6) | 0.0182 (6) | −0.0078 (6) |
O3 | 0.0482 (7) | 0.0864 (10) | 0.0816 (9) | −0.0191 (7) | 0.0407 (7) | −0.0157 (7) |
N1 | 0.0461 (8) | 0.0486 (8) | 0.0618 (9) | 0.0003 (6) | 0.0189 (7) | −0.0103 (7) |
C6 | 0.0325 (7) | 0.0458 (9) | 0.0473 (9) | −0.0036 (6) | 0.0153 (6) | −0.0010 (7) |
C7 | 0.0429 (8) | 0.0426 (9) | 0.0548 (10) | 0.0020 (7) | 0.0158 (8) | 0.0066 (7) |
C8 | 0.0509 (9) | 0.0554 (10) | 0.0452 (9) | 0.0027 (8) | 0.0142 (8) | 0.0142 (7) |
C9 | 0.0451 (9) | 0.0538 (10) | 0.0411 (8) | −0.0015 (7) | 0.0163 (7) | 0.0013 (7) |
C10 | 0.0336 (7) | 0.0395 (8) | 0.0423 (8) | −0.0059 (6) | 0.0114 (6) | 0.0000 (6) |
C11 | 0.0375 (8) | 0.0397 (8) | 0.0531 (9) | −0.0052 (6) | 0.0121 (7) | −0.0032 (7) |
C12 | 0.0564 (10) | 0.0414 (9) | 0.0743 (13) | 0.0032 (8) | 0.0241 (10) | 0.0119 (8) |
C13 | 0.0662 (12) | 0.0583 (11) | 0.0700 (12) | −0.0002 (9) | 0.0300 (10) | 0.0265 (10) |
C14 | 0.0517 (10) | 0.0575 (11) | 0.0545 (10) | −0.0016 (8) | 0.0264 (8) | 0.0113 (8) |
C15 | 0.0336 (7) | 0.0425 (8) | 0.0433 (8) | −0.0062 (6) | 0.0141 (6) | 0.0029 (6) |
C16 | 0.0507 (10) | 0.0686 (12) | 0.0671 (12) | 0.0000 (9) | 0.0263 (9) | −0.0005 (9) |
C17 | 0.0682 (13) | 0.0544 (11) | 0.0892 (15) | 0.0032 (10) | 0.0266 (12) | −0.0176 (10) |
C4 | 0.0332 (7) | 0.0499 (9) | 0.0360 (8) | −0.0049 (6) | 0.0136 (6) | −0.0008 (6) |
C3 | 0.0373 (8) | 0.0487 (9) | 0.0518 (9) | 0.0027 (6) | 0.0186 (7) | −0.0020 (7) |
C2 | 0.0446 (12) | 0.0440 (12) | 0.0577 (14) | 0.000 | 0.0208 (11) | 0.000 |
C5 | 0.0372 (10) | 0.0432 (12) | 0.0363 (11) | 0.000 | 0.0129 (9) | 0.000 |
C1 | 0.0671 (18) | 0.0455 (15) | 0.124 (3) | 0.000 | 0.0475 (19) | 0.000 |
S1—O1 | 1.6006 (12) | C13—H13 | 0.9300 |
S1—O2 | 1.4215 (14) | C13—C14 | 1.352 (3) |
S1—O3 | 1.4223 (13) | C14—H14 | 0.9300 |
S1—C6 | 1.7552 (16) | C14—C15 | 1.419 (2) |
O1—C4 | 1.4166 (17) | C16—H16A | 0.9600 |
N1—C11 | 1.413 (2) | C16—H16B | 0.9600 |
N1—C16 | 1.465 (2) | C16—H16C | 0.9600 |
N1—C17 | 1.458 (2) | C17—H17A | 0.9600 |
C6—C7 | 1.374 (2) | C17—H17B | 0.9600 |
C6—C15 | 1.426 (2) | C17—H17C | 0.9600 |
C7—H7 | 0.9300 | C4—C3 | 1.372 (2) |
C7—C8 | 1.399 (3) | C4—C5 | 1.3789 (19) |
C8—H8 | 0.9300 | C3—H3 | 0.9300 |
C8—C9 | 1.357 (2) | C3—C2 | 1.395 (2) |
C9—H9 | 0.9300 | C2—C3i | 1.395 (2) |
C9—C10 | 1.414 (2) | C2—C1 | 1.507 (3) |
C10—C11 | 1.435 (2) | C5—C4i | 1.3789 (19) |
C10—C15 | 1.426 (2) | C5—H5 | 0.9300 |
C11—C12 | 1.367 (3) | C1—H1A | 0.9600 |
C12—H12 | 0.9300 | C1—H1B | 0.9600 |
C12—C13 | 1.400 (3) | C1—H1C | 0.9600 |
O1—S1—C6 | 103.11 (7) | C13—C14—C15 | 119.53 (17) |
O2—S1—O1 | 108.81 (7) | C15—C14—H14 | 120.2 |
O2—S1—O3 | 119.32 (9) | C10—C15—C6 | 116.65 (14) |
O2—S1—C6 | 109.18 (8) | C14—C15—C6 | 124.57 (15) |
O3—S1—O1 | 102.86 (8) | C14—C15—C10 | 118.77 (15) |
O3—S1—C6 | 112.10 (8) | N1—C16—H16A | 109.5 |
C4—O1—S1 | 119.05 (9) | N1—C16—H16B | 109.5 |
C11—N1—C16 | 113.17 (14) | N1—C16—H16C | 109.5 |
C11—N1—C17 | 115.68 (16) | H16A—C16—H16B | 109.5 |
C17—N1—C16 | 110.26 (16) | H16A—C16—H16C | 109.5 |
C7—C6—S1 | 116.60 (13) | H16B—C16—H16C | 109.5 |
C7—C6—C15 | 122.16 (15) | N1—C17—H17A | 109.5 |
C15—C6—S1 | 121.22 (12) | N1—C17—H17B | 109.5 |
C6—C7—H7 | 120.1 | N1—C17—H17C | 109.5 |
C6—C7—C8 | 119.70 (15) | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 120.1 | H17A—C17—H17C | 109.5 |
C7—C8—H8 | 120.0 | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 120.03 (15) | C3—C4—O1 | 120.20 (13) |
C9—C8—H8 | 120.0 | C3—C4—C5 | 122.93 (15) |
C8—C9—H9 | 119.1 | C5—C4—O1 | 116.74 (14) |
C8—C9—C10 | 121.77 (16) | C4—C3—H3 | 120.3 |
C10—C9—H9 | 119.1 | C4—C3—C2 | 119.48 (16) |
C9—C10—C11 | 121.12 (15) | C2—C3—H3 | 120.3 |
C9—C10—C15 | 119.14 (14) | C3—C2—C3i | 118.7 (2) |
C15—C10—C11 | 119.69 (14) | C3i—C2—C1 | 120.64 (11) |
N1—C11—C10 | 118.03 (15) | C3—C2—C1 | 120.65 (11) |
C12—C11—N1 | 123.69 (16) | C4—C5—C4i | 116.5 (2) |
C12—C11—C10 | 118.28 (16) | C4—C5—H5 | 121.8 |
C11—C12—H12 | 119.5 | C4i—C5—H5 | 121.8 |
C11—C12—C13 | 121.09 (17) | C2—C1—H1A | 109.5 |
C13—C12—H12 | 119.5 | C2—C1—H1B | 109.5 |
C12—C13—H13 | 119.0 | C2—C1—H1C | 109.5 |
C14—C13—C12 | 122.05 (17) | H1A—C1—H1B | 109.5 |
C14—C13—H13 | 119.0 | H1A—C1—H1C | 109.5 |
C13—C14—H14 | 120.2 | H1B—C1—H1C | 109.5 |
S1—O1—C4—C3 | 72.98 (16) | C9—C10—C11—N1 | 11.1 (2) |
S1—O1—C4—C5 | −111.07 (11) | C9—C10—C11—C12 | −168.50 (16) |
S1—C6—C7—C8 | 178.93 (13) | C9—C10—C15—C6 | −8.3 (2) |
S1—C6—C15—C10 | −172.59 (11) | C9—C10—C15—C14 | 170.72 (15) |
S1—C6—C15—C14 | 8.4 (2) | C10—C11—C12—C13 | −4.8 (3) |
O1—S1—C6—C7 | −121.15 (13) | C11—C10—C15—C6 | 174.23 (13) |
O1—S1—C6—C15 | 57.51 (13) | C11—C10—C15—C14 | −6.7 (2) |
O1—C4—C3—C2 | 176.99 (11) | C11—C12—C13—C14 | −1.7 (3) |
O1—C4—C5—C4i | −176.50 (14) | C12—C13—C14—C15 | 4.0 (3) |
O2—S1—O1—C4 | −53.02 (13) | C13—C14—C15—C6 | 179.28 (16) |
O2—S1—C6—C7 | −5.58 (15) | C13—C14—C15—C10 | 0.3 (2) |
O2—S1—C6—C15 | 173.07 (12) | C15—C6—C7—C8 | 0.3 (2) |
O3—S1—O1—C4 | 179.51 (11) | C15—C10—C11—N1 | −171.45 (13) |
O3—S1—C6—C7 | 128.91 (14) | C15—C10—C11—C12 | 8.9 (2) |
O3—S1—C6—C15 | −52.44 (15) | C16—N1—C11—C10 | 68.68 (19) |
N1—C11—C12—C13 | 175.62 (17) | C16—N1—C11—C12 | −111.71 (19) |
C6—S1—O1—C4 | 62.80 (12) | C17—N1—C11—C10 | −162.74 (15) |
C6—C7—C8—C9 | −4.3 (3) | C17—N1—C11—C12 | 16.9 (2) |
C7—C6—C15—C10 | 6.0 (2) | C4—C3—C2—C3i | −0.62 (10) |
C7—C6—C15—C14 | −172.98 (16) | C4—C3—C2—C1 | 179.38 (10) |
C7—C8—C9—C10 | 1.8 (3) | C3—C4—C5—C4i | −0.66 (11) |
C8—C9—C10—C11 | −177.88 (15) | C5—C4—C3—C2 | 1.3 (2) |
C8—C9—C10—C15 | 4.7 (2) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O3 | 0.93 | 2.49 | 3.116 (2) | 125 |
C1—H1B···O3ii | 0.96 | 2.70 | 3.528 (2) | 145 |
C9—H9···O1iii | 0.93 | 2.60 | 3.486 (2) | 158 |
C16—H16C···O2iv | 0.96 | 2.63 | 3.475 (2) | 147 |
Symmetry codes: (ii) x+1/2, y+1/2, z; (iii) x, −y+1, z−1/2; (iv) x+1/2, y−1/2, z. |
Bond/angle | XRD | DFT |
S1—O1 | 1.6006 (12) | 1.647 |
S1—O3 | 1.4223 (13) | 1.453 |
S1—C6 | 1.7552 (16) | 1.768 |
O1—C4 | 1.4166 (17) | 1.394 |
N1—C11 | 1.413 (2) | 1.406 |
O1—S1—C6 | 103.11 (7) | 103.46 |
O2—S1—O1 | 108.81 (7) | 108.93 |
O2—S1—O3 | 119.32 (9) | 119.85 |
C4—O1—S1 | 119.05 (9) | 119.08 |
O2—S1—C6 | 109.18 (8) | 109.04 |
Acknowledgements
The authors thank the Thailand Research Fund (MRG5580182), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, the Kasetsart University Research and Development Institute and the Department of Chemistry, Kasetsart University for financial support.
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