research communications
S-hexyl (E)-3-(2-hydroxybenzylidene)dithiocarbazate
ofaDepartment of Chemistry, Shahjalal University of Science and Technology, Sylhet 3114, Bangladesh, bDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, cDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, dCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and eDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127 Trieste, Italy
*Correspondence e-mail: mbhhowlader@gmail.com
The title compound, C14H20N2OS2 [systematic name: S-hexyl (E)-2-(2-hydroxybenzylidene)hydrazine-1-carbodithioate], crystallizes with four independent molecules (A–D) in the All four molecules adopt an E conformation with respect to the C=N bond of the benzylidene moiety and have an intramolecular O—H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, the A and D molecules are connected by a pair N—H⋯S hydrogen bonds, forming a dimer with an R22(8) ring motif. In the case of molecules B and C, they are linked to themselves by pairs of N—H⋯S hydrogen bonds, forming B–B and C–C inversion dimers with R22(8) ring motifs.
Keywords: crystal structure; dithiocarbazate; S-containing Schiff base; tridentate ligand; hydrogen bonding.
CCDC reference: 1451068
1. Chemical context
Bidentate et al., 2008; How et al., 2008; Zangrando et al., 2015; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing we report herein on the structure of a molecule having a hexyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015; Begum, Howlader, Miyatake et al., 2015; Howlader et al., 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015).
of S-methyl or S-benzyl dithiocarbazates and their metal complexes have received considerable attention for their possible bioactivities (Chan2. Structural commentary
The four independent molecules (A--D) of the title compound are shown in Figs. 1 and 2. The Schiff base exists in its thione tautomeric form with the dithiocarbazate fragment adopting an E conformation with respect to the C=N bond of the benzylidene moiety. The β-nitrogen and the thioketo sulfur are trans located with respect to bond C8—N2 bond in molecule A (and similarly for molecules B, C and D). All non-H atoms in the molecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thioketone atoms S1, S3, S5 and S7 in the four independent molecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methylbenzylidene)dithiocarbazate (Howlader et al., 2015) and S-hexyl (E)-3-(4-methoxybenzylidene)dithiocarbazate (Begum, Howlader, Miyatake et al., 2015). The hexyl chain in all four molecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiolate form has been reported to act as a tridentate ligand through N-, S- and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015).
3. Supramolecular features
The crystal packing of the title compound (Fig. 3), indicates that the molecules are connected by pairs of N—H⋯S hydrogen bonds (Table 1) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.
4. Synthesis and crystallization
To an ethanolic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon disulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then, 1-bromohexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hydroxybenzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/acetonitrile (3:1) [m.p. 364 K].
5. Refinement
Crystal data, data collection and structure . Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The hydrogen atoms of NH and OH groups were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).
details are summarized in Table 2
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Supporting information
CCDC reference: 1451068
10.1107/S2056989016001857/su5276sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016001857/su5276Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016001857/su5276Isup3.cml
Bidentate
of S-methyl or S-benzyl dithiocarbazates and their metal complexes have received considerable attention for their possible bioactivities (Chan et al., 2008; How et al., 2008; Zangrando et al., 2015; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing we report herein on the structure of a molecule having a hexyl alkyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015; Begum, Howlader, Miyatake et al., 2015; Howlader et al., 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015).The four independent molecules (A--D) of the title compound are shown in Figs. 1 and 2. The Schiff base exists in its thione tautomeric form with the dithiocarbazate fragment adopting an E conformation with respect to the C═N bond of the benzylidene moiety. The β-nitrogen and the thioketo sulfur are trans located with respect to bond C8—N2 bond in molecule A (and similarly for molecules B, C and D). All non-H atoms in the molecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thioketone atoms S1, S3, S5 and S7 in the four independent molecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methylbenzylidene)dithiocarbazate (Howlader et al., 2015) and S-hexyl (E)-3-(4-methoxybenzylidene)dithiocarbazate (Begum, Howlader, Miyatake et al., 2015). The hexyl chain in all four molecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiolate form has been reported to act as a tridentate ligand through N–, S– and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015).
The crystal packing of the title compound (Fig. 2), indicates that the molecules are connected by pairs of N—H···S hydrogen bonds (Table 1) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.
To an ethanolic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon disulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then 1-bromohexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hydroxybenzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/acetonitrile (3:1) [m.p. 364 K].
Crystal data, data collection and structure
details are summarized in Table 2. Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The NH and OH H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).Bidentate
of S-methyl or S-benzyl dithiocarbazates and their metal complexes have received considerable attention for their possible bioactivities (Chan et al., 2008; How et al., 2008; Zangrando et al., 2015; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing we report herein on the structure of a molecule having a hexyl alkyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015; Begum, Howlader, Miyatake et al., 2015; Howlader et al., 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015).The four independent molecules (A--D) of the title compound are shown in Figs. 1 and 2. The Schiff base exists in its thione tautomeric form with the dithiocarbazate fragment adopting an E conformation with respect to the C═N bond of the benzylidene moiety. The β-nitrogen and the thioketo sulfur are trans located with respect to bond C8—N2 bond in molecule A (and similarly for molecules B, C and D). All non-H atoms in the molecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thioketone atoms S1, S3, S5 and S7 in the four independent molecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methylbenzylidene)dithiocarbazate (Howlader et al., 2015) and S-hexyl (E)-3-(4-methoxybenzylidene)dithiocarbazate (Begum, Howlader, Miyatake et al., 2015). The hexyl chain in all four molecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiolate form has been reported to act as a tridentate ligand through N–, S– and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015).
The crystal packing of the title compound (Fig. 2), indicates that the molecules are connected by pairs of N—H···S hydrogen bonds (Table 1) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.
To an ethanolic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon disulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then 1-bromohexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hydroxybenzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/acetonitrile (3:1) [m.p. 364 K].
detailsCrystal data, data collection and structure
details are summarized in Table 2. Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The NH and OH H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).Data collection: RAPID-AUTO (Rigaku, 2001); cell
RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).Fig. 1. The molecular structure of molecules A and C of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The molecular structure of molecules B and D of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 3. Crystal packing of the title compound, viewed along the c axis, showing pairs of molecules connected by N—H.·S hydrogen bonds (dashed lines; see Table 1). H atoms not involved in hydrogen bonds have been omitted for clarity. |
C14H20N2OS2 | F(000) = 2528 |
Mr = 296.44 | Dx = 1.249 Mg m−3 |
Monoclinic, P2/c | Cu Kα radiation, λ = 1.54187 Å |
a = 18.9744 (4) Å | Cell parameters from 48491 reflections |
b = 16.0269 (3) Å | θ = 3.5–68.2° |
c = 21.1146 (4) Å | µ = 3.01 mm−1 |
β = 100.808 (1)° | T = 173 K |
V = 6307.1 (2) Å3 | Block, colourless |
Z = 16 | 0.50 × 0.35 × 0.34 mm |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.072 |
Detector resolution: 10.000 pixels mm-1 | θmax = 63.7°, θmin = 3.5° |
ω scans | h = −22→22 |
10367 measured reflections | k = −19→19 |
10367 independent reflections | l = −25→25 |
6152 reflections with I > 2σ(I) |
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)] = 0.065 | Hydrogen site location: mixed |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.1083P)2] where P = (Fo2 + 2Fc2)/3 |
10367 reflections | (Δ/σ)max = 0.001 |
713 parameters | Δρmax = 1.01 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C14H20N2OS2 | V = 6307.1 (2) Å3 |
Mr = 296.44 | Z = 16 |
Monoclinic, P2/c | Cu Kα radiation |
a = 18.9744 (4) Å | µ = 3.01 mm−1 |
b = 16.0269 (3) Å | T = 173 K |
c = 21.1146 (4) Å | 0.50 × 0.35 × 0.34 mm |
β = 100.808 (1)° |
Rigaku R-AXIS RAPID diffractometer | 6152 reflections with I > 2σ(I) |
10367 measured reflections | Rint = 0.072 |
10367 independent reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 0.93 | Δρmax = 1.01 e Å−3 |
10367 reflections | Δρmin = −0.46 e Å−3 |
713 parameters |
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 | ||
S1 | 0.25358 (4) | 0.59787 (5) | 1.25919 (4) | 0.0533 (2) | |
S2 | 0.10299 (4) | 0.66115 (5) | 1.21116 (4) | 0.0461 (2) | |
O1 | −0.06852 (11) | 0.53508 (15) | 1.15318 (11) | 0.0557 (6) | |
H1O | −0.0321 (17) | 0.550 (2) | 1.1640 (16) | 0.067* | |
N1 | 0.06892 (12) | 0.49125 (15) | 1.19459 (10) | 0.0410 (6) | |
N2 | 0.14075 (12) | 0.50536 (15) | 1.21817 (11) | 0.0417 (6) | |
H2N | 0.1694 (15) | 0.4634 (17) | 1.2249 (13) | 0.050* | |
C1 | −0.08129 (16) | 0.4524 (2) | 1.14951 (13) | 0.0447 (7) | |
C2 | −0.15168 (17) | 0.4254 (2) | 1.13090 (14) | 0.0570 (9) | |
H2 | −0.1893 | 0.4651 | 1.1212 | 0.068* | |
C3 | −0.16709 (17) | 0.3420 (2) | 1.12649 (15) | 0.0617 (9) | |
H3 | −0.2155 | 0.3247 | 1.1136 | 0.074* | |
C4 | −0.11444 (17) | 0.2829 (2) | 1.14023 (14) | 0.0584 (9) | |
H4 | −0.1261 | 0.2252 | 1.1369 | 0.070* | |
C5 | −0.04406 (16) | 0.30837 (19) | 1.15911 (13) | 0.0508 (8) | |
H5 | −0.0073 | 0.2675 | 1.1688 | 0.061* | |
C6 | −0.02564 (15) | 0.39267 (19) | 1.16431 (12) | 0.0418 (7) | |
C7 | 0.04852 (14) | 0.41577 (18) | 1.18721 (12) | 0.0409 (7) | |
H7 | 0.0833 | 0.3728 | 1.1971 | 0.049* | |
C8 | 0.16649 (15) | 0.58236 (18) | 1.22957 (13) | 0.0410 (7) | |
C9 | 0.15769 (15) | 0.75494 (17) | 1.22512 (14) | 0.0445 (7) | |
H9A | 0.1819 | 0.7579 | 1.2709 | 0.053* | |
H9B | 0.1949 | 0.7542 | 1.1979 | 0.053* | |
C10 | 0.10842 (14) | 0.83027 (17) | 1.20813 (13) | 0.0434 (7) | |
H10A | 0.0840 | 0.8264 | 1.1625 | 0.052* | |
H10B | 0.0712 | 0.8300 | 1.2353 | 0.052* | |
C11 | 0.15059 (15) | 0.91139 (17) | 1.21864 (13) | 0.0420 (7) | |
H11A | 0.1756 | 0.9143 | 1.2642 | 0.050* | |
H11B | 0.1875 | 0.9115 | 1.1911 | 0.050* | |
C12 | 0.10336 (14) | 0.98812 (18) | 1.20317 (13) | 0.0437 (7) | |
H12A | 0.0643 | 0.9857 | 1.2283 | 0.052* | |
H12B | 0.0811 | 0.9871 | 1.1568 | 0.052* | |
C13 | 0.14401 (15) | 1.06987 (18) | 1.21809 (14) | 0.0474 (8) | |
H13A | 0.1664 | 1.0710 | 1.2644 | 0.057* | |
H13B | 0.1830 | 1.0726 | 1.1928 | 0.057* | |
C14 | 0.09630 (16) | 1.14567 (19) | 1.20269 (16) | 0.0633 (10) | |
H14A | 0.0737 | 1.1448 | 1.1570 | 0.095* | |
H14B | 0.1252 | 1.1964 | 1.2119 | 0.095* | |
H14C | 0.0591 | 1.1449 | 1.2292 | 0.095* | |
S3 | −0.00414 (4) | 0.86442 (5) | 0.98657 (4) | 0.0615 (3) | |
S4 | 0.14581 (4) | 0.80245 (5) | 1.04021 (4) | 0.0527 (2) | |
O2 | 0.31627 (12) | 0.92929 (17) | 1.09819 (11) | 0.0628 (7) | |
H2O | 0.2772 (18) | 0.913 (2) | 1.0877 (17) | 0.075* | |
N3 | 0.17915 (13) | 0.97231 (16) | 1.05390 (10) | 0.0453 (6) | |
N4 | 0.10796 (14) | 0.95825 (16) | 1.02840 (12) | 0.0483 (7) | |
H4N | 0.0804 (16) | 0.997 (2) | 1.0216 (14) | 0.058* | |
C15 | 0.32870 (17) | 1.0119 (2) | 1.10127 (13) | 0.0511 (8) | |
C16 | 0.39934 (17) | 1.0388 (3) | 1.12158 (15) | 0.0620 (10) | |
H16 | 0.4367 | 0.9990 | 1.1329 | 0.074* | |
C17 | 0.41471 (19) | 1.1219 (3) | 1.12517 (15) | 0.0678 (10) | |
H17 | 0.4632 | 1.1390 | 1.1384 | 0.081* | |
C18 | 0.36200 (18) | 1.1823 (2) | 1.11015 (15) | 0.0640 (10) | |
H18 | 0.3736 | 1.2400 | 1.1139 | 0.077* | |
C19 | 0.29206 (18) | 1.1563 (2) | 1.08951 (14) | 0.0581 (9) | |
H19 | 0.2555 | 1.1970 | 1.0784 | 0.070* | |
C20 | 0.27352 (16) | 1.0720 (2) | 1.08446 (13) | 0.0461 (8) | |
C21 | 0.19920 (16) | 1.0485 (2) | 1.06038 (13) | 0.0467 (8) | |
H21 | 0.1644 | 1.0912 | 1.0491 | 0.056* | |
C22 | 0.08232 (16) | 0.8808 (2) | 1.01810 (14) | 0.0484 (8) | |
C23 | 0.09183 (16) | 0.70822 (19) | 1.02657 (14) | 0.0519 (8) | |
H23A | 0.0551 | 0.7084 | 1.0543 | 0.062* | |
H23B | 0.0670 | 0.7055 | 0.9810 | 0.062* | |
C24 | 0.14087 (15) | 0.63370 (19) | 1.04250 (14) | 0.0509 (8) | |
H24A | 0.1650 | 0.6365 | 1.0883 | 0.061* | |
H24B | 0.1783 | 0.6350 | 1.0156 | 0.061* | |
C25 | 0.09880 (15) | 0.55256 (19) | 1.03051 (14) | 0.0516 (8) | |
H25A | 0.0633 | 0.5504 | 1.0594 | 0.062* | |
H25B | 0.0720 | 0.5522 | 0.9855 | 0.062* | |
C26 | 0.14574 (16) | 0.4750 (2) | 1.04161 (15) | 0.0540 (8) | |
H26A | 0.1696 | 0.4730 | 1.0875 | 0.065* | |
H26B | 0.1836 | 0.4791 | 1.0152 | 0.065* | |
C27 | 0.10385 (17) | 0.3945 (2) | 1.02465 (16) | 0.0613 (9) | |
H27A | 0.0652 | 0.3912 | 1.0502 | 0.074* | |
H27B | 0.0810 | 0.3960 | 0.9785 | 0.074* | |
C28 | 0.15007 (18) | 0.3170 (2) | 1.03720 (17) | 0.0776 (11) | |
H28A | 0.1879 | 0.3192 | 1.0114 | 0.116* | |
H28B | 0.1203 | 0.2674 | 1.0253 | 0.116* | |
H28C | 0.1719 | 0.3143 | 1.0830 | 0.116* | |
S5 | 0.50812 (4) | 0.86393 (5) | 1.02000 (4) | 0.0560 (3) | |
S6 | 0.36038 (4) | 0.79983 (5) | 0.96181 (4) | 0.0481 (2) | |
O3 | 0.19255 (11) | 0.91698 (14) | 0.90094 (10) | 0.0553 (6) | |
H3O | 0.2367 (16) | 0.913 (2) | 0.9149 (15) | 0.066* | |
N5 | 0.32576 (12) | 0.96786 (14) | 0.94728 (10) | 0.0384 (6) | |
N6 | 0.39644 (12) | 0.95587 (15) | 0.97387 (11) | 0.0425 (6) | |
H6N | 0.4245 (15) | 0.9962 (19) | 0.9840 (13) | 0.051* | |
C29 | 0.17628 (15) | 0.9992 (2) | 0.89769 (12) | 0.0433 (7) | |
C30 | 0.10555 (16) | 1.0218 (2) | 0.87630 (14) | 0.0541 (8) | |
H30 | 0.0703 | 0.9797 | 0.8640 | 0.065* | |
C31 | 0.08572 (17) | 1.1037 (2) | 0.87262 (14) | 0.0573 (9) | |
H31 | 0.0365 | 1.1176 | 0.8590 | 0.069* | |
C32 | 0.13576 (17) | 1.1674 (2) | 0.88835 (14) | 0.0565 (9) | |
H32 | 0.1215 | 1.2243 | 0.8848 | 0.068* | |
C33 | 0.20673 (16) | 1.14573 (19) | 0.90922 (13) | 0.0476 (8) | |
H33 | 0.2414 | 1.1886 | 0.9202 | 0.057* | |
C34 | 0.22898 (15) | 1.06259 (19) | 0.91474 (12) | 0.0399 (7) | |
C35 | 0.30375 (15) | 1.04327 (18) | 0.94067 (12) | 0.0397 (7) | |
H35 | 0.3368 | 1.0875 | 0.9529 | 0.048* | |
C36 | 0.42271 (15) | 0.87873 (19) | 0.98566 (13) | 0.0428 (7) | |
C37 | 0.41480 (15) | 0.70616 (18) | 0.97630 (14) | 0.0460 (7) | |
H37A | 0.4535 | 0.7076 | 0.9508 | 0.055* | |
H37B | 0.4370 | 0.7020 | 1.0225 | 0.055* | |
C38 | 0.36595 (15) | 0.63222 (17) | 0.95638 (13) | 0.0446 (7) | |
H38A | 0.3448 | 0.6369 | 0.9100 | 0.053* | |
H38B | 0.3262 | 0.6332 | 0.9808 | 0.053* | |
C39 | 0.40588 (14) | 0.54952 (17) | 0.96853 (13) | 0.0433 (7) | |
H39A | 0.4275 | 0.5451 | 1.0149 | 0.052* | |
H39B | 0.4453 | 0.5483 | 0.9437 | 0.052* | |
C40 | 0.35648 (15) | 0.47508 (18) | 0.94918 (14) | 0.0456 (7) | |
H40A | 0.3358 | 0.4792 | 0.9026 | 0.055* | |
H40B | 0.3164 | 0.4775 | 0.9731 | 0.055* | |
C41 | 0.39454 (16) | 0.39093 (18) | 0.96230 (15) | 0.0525 (8) | |
H41A | 0.4325 | 0.3868 | 0.9361 | 0.063* | |
H41B | 0.4179 | 0.3881 | 1.0083 | 0.063* | |
C42 | 0.34353 (17) | 0.31711 (19) | 0.94668 (16) | 0.0638 (9) | |
H42A | 0.3058 | 0.3208 | 0.9725 | 0.096* | |
H42B | 0.3703 | 0.2650 | 0.9567 | 0.096* | |
H42C | 0.3218 | 0.3182 | 0.9008 | 0.096* | |
S7 | 0.24114 (4) | 0.67360 (5) | 0.72575 (4) | 0.0532 (2) | |
S8 | 0.38731 (4) | 0.73717 (5) | 0.78991 (4) | 0.0467 (2) | |
O4 | 0.55528 (11) | 0.61947 (14) | 0.85012 (11) | 0.0557 (6) | |
H4O | 0.5165 (16) | 0.625 (2) | 0.8343 (15) | 0.067* | |
N7 | 0.42251 (12) | 0.56890 (14) | 0.80139 (10) | 0.0384 (6) | |
N8 | 0.35164 (13) | 0.58122 (15) | 0.77368 (11) | 0.0406 (6) | |
H8N | 0.3267 (15) | 0.5403 (17) | 0.7596 (13) | 0.049* | |
C43 | 0.57105 (15) | 0.5377 (2) | 0.85318 (12) | 0.0423 (7) | |
C44 | 0.64194 (16) | 0.5149 (2) | 0.87552 (14) | 0.0518 (8) | |
H44 | 0.6771 | 0.5569 | 0.8880 | 0.062* | |
C45 | 0.66183 (17) | 0.4330 (2) | 0.87981 (15) | 0.0579 (9) | |
H45 | 0.7107 | 0.4190 | 0.8952 | 0.069* | |
C46 | 0.61212 (17) | 0.3694 (2) | 0.86216 (14) | 0.0534 (8) | |
H46 | 0.6265 | 0.3125 | 0.8652 | 0.064* | |
C47 | 0.54122 (16) | 0.39123 (19) | 0.84007 (13) | 0.0465 (8) | |
H47 | 0.5066 | 0.3485 | 0.8283 | 0.056* | |
C48 | 0.51916 (15) | 0.47465 (18) | 0.83465 (12) | 0.0384 (7) | |
C49 | 0.44460 (14) | 0.49335 (18) | 0.80773 (12) | 0.0385 (7) | |
H49 | 0.4119 | 0.4490 | 0.7947 | 0.046* | |
C50 | 0.32545 (15) | 0.65816 (17) | 0.76239 (13) | 0.0406 (7) | |
C51 | 0.33330 (15) | 0.83076 (17) | 0.77494 (14) | 0.0448 (7) | |
H51A | 0.3105 | 0.8341 | 0.7288 | 0.054* | |
H51B | 0.2950 | 0.8301 | 0.8010 | 0.054* | |
C52 | 0.38231 (15) | 0.90513 (18) | 0.79341 (13) | 0.0445 (7) | |
H52A | 0.4035 | 0.9018 | 0.8399 | 0.053* | |
H52B | 0.4220 | 0.9030 | 0.7690 | 0.053* | |
C53 | 0.34310 (14) | 0.98712 (17) | 0.77993 (13) | 0.0424 (7) | |
H53A | 0.3051 | 0.9904 | 0.8061 | 0.051* | |
H53B | 0.3196 | 0.9889 | 0.7339 | 0.051* | |
C54 | 0.39254 (15) | 1.06271 (19) | 0.79491 (14) | 0.0503 (8) | |
H54A | 0.4157 | 1.0610 | 0.8410 | 0.060* | |
H54B | 0.4308 | 1.0590 | 0.7690 | 0.060* | |
C55 | 0.35385 (16) | 1.14549 (18) | 0.78102 (16) | 0.0558 (8) | |
H55A | 0.3290 | 1.1464 | 0.7354 | 0.067* | |
H55B | 0.3170 | 1.1504 | 0.8083 | 0.067* | |
C56 | 0.40366 (17) | 1.2195 (2) | 0.79334 (17) | 0.0731 (11) | |
H56A | 0.4289 | 1.2187 | 0.8383 | 0.110* | |
H56B | 0.3758 | 1.2711 | 0.7851 | 0.110* | |
H56C | 0.4386 | 1.2168 | 0.7646 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0338 (4) | 0.0394 (5) | 0.0820 (6) | 0.0012 (3) | −0.0012 (4) | −0.0004 (4) |
S2 | 0.0352 (4) | 0.0406 (5) | 0.0594 (5) | 0.0030 (3) | 0.0010 (4) | 0.0001 (3) |
O1 | 0.0457 (14) | 0.0542 (16) | 0.0627 (15) | 0.0107 (12) | −0.0012 (12) | 0.0022 (11) |
N1 | 0.0363 (14) | 0.0479 (16) | 0.0359 (13) | 0.0039 (12) | −0.0004 (10) | 0.0023 (11) |
N2 | 0.0328 (15) | 0.0369 (16) | 0.0521 (15) | 0.0001 (11) | −0.0009 (12) | 0.0001 (12) |
C1 | 0.0446 (19) | 0.0429 (19) | 0.0439 (17) | 0.0016 (15) | 0.0013 (14) | −0.0036 (14) |
C2 | 0.0351 (19) | 0.085 (3) | 0.0477 (19) | 0.0163 (18) | −0.0011 (15) | 0.0004 (17) |
C3 | 0.043 (2) | 0.079 (3) | 0.060 (2) | −0.012 (2) | 0.0005 (16) | −0.0065 (19) |
C4 | 0.050 (2) | 0.062 (2) | 0.059 (2) | −0.0170 (18) | −0.0012 (16) | −0.0047 (17) |
C5 | 0.0436 (19) | 0.0424 (19) | 0.063 (2) | −0.0008 (15) | 0.0013 (16) | −0.0044 (15) |
C6 | 0.0374 (17) | 0.052 (2) | 0.0343 (15) | 0.0055 (15) | 0.0029 (13) | 0.0006 (13) |
C7 | 0.0365 (17) | 0.0345 (17) | 0.0490 (17) | −0.0019 (14) | 0.0010 (14) | −0.0019 (13) |
C8 | 0.0379 (17) | 0.048 (2) | 0.0360 (15) | 0.0048 (14) | 0.0049 (13) | 0.0039 (13) |
C9 | 0.0395 (17) | 0.0316 (16) | 0.0600 (18) | −0.0020 (13) | 0.0028 (14) | −0.0030 (14) |
C10 | 0.0420 (18) | 0.0375 (18) | 0.0498 (17) | 0.0052 (14) | 0.0063 (14) | −0.0042 (13) |
C11 | 0.0392 (17) | 0.0379 (18) | 0.0473 (17) | 0.0023 (14) | 0.0042 (14) | −0.0006 (13) |
C12 | 0.0376 (17) | 0.0402 (18) | 0.0507 (18) | 0.0040 (14) | 0.0014 (14) | 0.0000 (14) |
C13 | 0.0400 (18) | 0.0416 (19) | 0.0580 (19) | −0.0014 (14) | 0.0026 (15) | −0.0004 (14) |
C14 | 0.060 (2) | 0.040 (2) | 0.084 (2) | 0.0006 (17) | 0.0009 (19) | −0.0033 (17) |
S3 | 0.0391 (5) | 0.0544 (6) | 0.0868 (6) | 0.0014 (4) | 0.0009 (4) | 0.0056 (4) |
S4 | 0.0424 (5) | 0.0528 (6) | 0.0598 (5) | 0.0060 (4) | 0.0017 (4) | 0.0058 (4) |
O2 | 0.0508 (15) | 0.0648 (18) | 0.0687 (16) | 0.0107 (14) | 0.0011 (13) | 0.0046 (12) |
N3 | 0.0386 (15) | 0.0561 (18) | 0.0402 (14) | 0.0042 (13) | 0.0048 (11) | 0.0042 (12) |
N4 | 0.0410 (17) | 0.0464 (18) | 0.0548 (16) | 0.0038 (13) | 0.0021 (13) | 0.0060 (13) |
C15 | 0.048 (2) | 0.065 (2) | 0.0386 (17) | 0.0035 (18) | 0.0051 (15) | −0.0020 (16) |
C16 | 0.040 (2) | 0.088 (3) | 0.054 (2) | 0.0099 (19) | 0.0001 (16) | −0.0031 (19) |
C17 | 0.049 (2) | 0.094 (3) | 0.057 (2) | −0.015 (2) | 0.0015 (17) | −0.013 (2) |
C18 | 0.053 (2) | 0.070 (3) | 0.066 (2) | −0.010 (2) | 0.0029 (18) | −0.0135 (18) |
C19 | 0.053 (2) | 0.059 (2) | 0.060 (2) | −0.0014 (18) | 0.0036 (17) | −0.0041 (17) |
C20 | 0.0395 (18) | 0.059 (2) | 0.0387 (16) | 0.0057 (16) | 0.0040 (14) | 0.0013 (14) |
C21 | 0.0424 (19) | 0.053 (2) | 0.0440 (17) | 0.0034 (16) | 0.0072 (14) | 0.0014 (15) |
C22 | 0.0444 (19) | 0.056 (2) | 0.0442 (17) | 0.0032 (16) | 0.0061 (14) | 0.0035 (15) |
C23 | 0.0451 (19) | 0.054 (2) | 0.0563 (19) | 0.0072 (16) | 0.0082 (15) | 0.0068 (15) |
C24 | 0.045 (2) | 0.055 (2) | 0.0524 (19) | 0.0034 (16) | 0.0092 (15) | 0.0016 (15) |
C25 | 0.0440 (19) | 0.060 (2) | 0.0486 (18) | 0.0092 (17) | 0.0041 (15) | 0.0039 (15) |
C26 | 0.045 (2) | 0.057 (2) | 0.059 (2) | 0.0062 (17) | 0.0073 (16) | 0.0005 (16) |
C27 | 0.048 (2) | 0.065 (2) | 0.070 (2) | 0.0042 (18) | 0.0062 (17) | 0.0011 (18) |
C28 | 0.073 (3) | 0.062 (3) | 0.093 (3) | 0.005 (2) | 0.004 (2) | −0.007 (2) |
S5 | 0.0355 (5) | 0.0451 (5) | 0.0812 (6) | −0.0009 (4) | −0.0053 (4) | −0.0014 (4) |
S6 | 0.0391 (5) | 0.0375 (5) | 0.0627 (5) | −0.0030 (3) | −0.0036 (4) | −0.0002 (3) |
O3 | 0.0466 (13) | 0.0426 (13) | 0.0691 (15) | −0.0093 (11) | −0.0084 (12) | 0.0045 (10) |
N5 | 0.0343 (14) | 0.0380 (15) | 0.0404 (13) | −0.0031 (11) | 0.0002 (11) | −0.0025 (10) |
N6 | 0.0307 (15) | 0.0404 (16) | 0.0518 (15) | −0.0038 (11) | −0.0043 (12) | −0.0035 (12) |
C29 | 0.0376 (18) | 0.052 (2) | 0.0373 (16) | −0.0075 (15) | −0.0005 (13) | 0.0028 (14) |
C30 | 0.0400 (19) | 0.063 (2) | 0.0559 (19) | −0.0093 (17) | −0.0001 (15) | 0.0054 (16) |
C31 | 0.0375 (19) | 0.076 (3) | 0.056 (2) | 0.0070 (18) | 0.0017 (15) | 0.0084 (18) |
C32 | 0.050 (2) | 0.058 (2) | 0.058 (2) | 0.0107 (18) | 0.0020 (16) | 0.0035 (16) |
C33 | 0.0447 (19) | 0.043 (2) | 0.0521 (18) | 0.0003 (15) | 0.0022 (15) | −0.0013 (14) |
C34 | 0.0355 (17) | 0.0462 (19) | 0.0357 (15) | −0.0020 (14) | 0.0010 (13) | 0.0014 (13) |
C35 | 0.0367 (17) | 0.0412 (19) | 0.0401 (16) | −0.0071 (14) | 0.0045 (13) | −0.0032 (13) |
C36 | 0.0389 (18) | 0.0433 (19) | 0.0444 (16) | 0.0014 (14) | 0.0030 (13) | −0.0003 (14) |
C37 | 0.0410 (18) | 0.0420 (18) | 0.0518 (18) | 0.0007 (14) | 0.0008 (14) | 0.0037 (14) |
C38 | 0.0439 (18) | 0.0402 (18) | 0.0466 (17) | 0.0000 (14) | 0.0007 (14) | 0.0054 (13) |
C39 | 0.0371 (17) | 0.047 (2) | 0.0438 (17) | −0.0035 (14) | 0.0030 (14) | 0.0008 (14) |
C40 | 0.0393 (18) | 0.0438 (19) | 0.0519 (18) | −0.0031 (14) | 0.0041 (14) | −0.0016 (14) |
C41 | 0.0446 (19) | 0.048 (2) | 0.064 (2) | 0.0002 (16) | 0.0060 (16) | −0.0003 (16) |
C42 | 0.058 (2) | 0.043 (2) | 0.088 (2) | −0.0056 (17) | 0.0053 (19) | −0.0039 (17) |
S7 | 0.0354 (5) | 0.0434 (5) | 0.0758 (6) | 0.0005 (3) | −0.0025 (4) | 0.0030 (4) |
S8 | 0.0410 (5) | 0.0362 (5) | 0.0580 (5) | −0.0009 (3) | −0.0035 (4) | −0.0021 (3) |
O4 | 0.0502 (14) | 0.0400 (13) | 0.0693 (15) | −0.0074 (12) | −0.0082 (12) | 0.0024 (11) |
N7 | 0.0349 (14) | 0.0360 (14) | 0.0420 (13) | −0.0009 (11) | 0.0015 (11) | −0.0006 (10) |
N8 | 0.0346 (15) | 0.0361 (16) | 0.0475 (14) | −0.0028 (11) | −0.0016 (12) | −0.0048 (11) |
C43 | 0.0374 (18) | 0.054 (2) | 0.0348 (15) | −0.0084 (15) | 0.0040 (13) | 0.0003 (13) |
C44 | 0.0380 (18) | 0.059 (2) | 0.0554 (19) | −0.0058 (16) | 0.0021 (15) | 0.0042 (16) |
C45 | 0.0395 (19) | 0.083 (3) | 0.0508 (19) | 0.0036 (19) | 0.0078 (15) | 0.0061 (18) |
C46 | 0.048 (2) | 0.053 (2) | 0.057 (2) | 0.0119 (17) | 0.0044 (16) | 0.0045 (16) |
C47 | 0.0459 (19) | 0.046 (2) | 0.0471 (17) | −0.0016 (15) | 0.0068 (15) | −0.0045 (14) |
C48 | 0.0350 (16) | 0.0413 (17) | 0.0385 (16) | −0.0005 (14) | 0.0056 (13) | 0.0019 (13) |
C49 | 0.0366 (17) | 0.0423 (18) | 0.0357 (15) | −0.0079 (14) | 0.0048 (13) | −0.0045 (13) |
C50 | 0.0388 (17) | 0.0366 (17) | 0.0461 (16) | 0.0003 (14) | 0.0068 (13) | 0.0013 (13) |
C51 | 0.0382 (17) | 0.0439 (19) | 0.0482 (17) | 0.0006 (14) | −0.0023 (14) | 0.0003 (14) |
C52 | 0.0456 (18) | 0.0446 (19) | 0.0408 (16) | −0.0044 (15) | 0.0014 (14) | −0.0005 (13) |
C53 | 0.0424 (18) | 0.0390 (18) | 0.0439 (16) | −0.0013 (14) | 0.0031 (14) | −0.0011 (13) |
C54 | 0.0434 (19) | 0.044 (2) | 0.061 (2) | −0.0043 (15) | 0.0049 (16) | −0.0016 (15) |
C55 | 0.046 (2) | 0.0397 (19) | 0.081 (2) | −0.0017 (15) | 0.0100 (17) | −0.0015 (16) |
C56 | 0.063 (2) | 0.044 (2) | 0.111 (3) | −0.0017 (18) | 0.012 (2) | 0.006 (2) |
S1—C8 | 1.672 (3) | S5—C36 | 1.664 (3) |
S2—C8 | 1.738 (3) | S6—C36 | 1.740 (3) |
S2—C9 | 1.819 (3) | S6—C37 | 1.815 (3) |
O1—C1 | 1.347 (4) | O3—C29 | 1.353 (4) |
O1—H1O | 0.73 (3) | O3—H3O | 0.84 (3) |
N1—C7 | 1.271 (3) | N5—C35 | 1.278 (3) |
N1—N2 | 1.379 (3) | N5—N6 | 1.367 (3) |
N2—C8 | 1.332 (3) | N6—C36 | 1.339 (4) |
N2—H2N | 0.86 (3) | N6—H6N | 0.84 (3) |
C1—C2 | 1.389 (4) | C29—C30 | 1.381 (4) |
C1—C6 | 1.416 (4) | C29—C34 | 1.423 (4) |
C2—C3 | 1.368 (5) | C30—C31 | 1.364 (4) |
C2—H2 | 0.9500 | C30—H30 | 0.9500 |
C3—C4 | 1.368 (4) | C31—C32 | 1.392 (4) |
C3—H3 | 0.9500 | C31—H31 | 0.9500 |
C4—C5 | 1.382 (4) | C32—C33 | 1.380 (4) |
C4—H4 | 0.9500 | C32—H32 | 0.9500 |
C5—C6 | 1.395 (4) | C33—C34 | 1.396 (4) |
C5—H5 | 0.9500 | C33—H33 | 0.9500 |
C6—C7 | 1.448 (4) | C34—C35 | 1.455 (4) |
C7—H7 | 0.9500 | C35—H35 | 0.9500 |
C9—C10 | 1.528 (4) | C37—C38 | 1.515 (4) |
C9—H9A | 0.9900 | C37—H37A | 0.9900 |
C9—H9B | 0.9900 | C37—H37B | 0.9900 |
C10—C11 | 1.521 (4) | C38—C39 | 1.524 (4) |
C10—H10A | 0.9900 | C38—H38A | 0.9900 |
C10—H10B | 0.9900 | C38—H38B | 0.9900 |
C11—C12 | 1.521 (4) | C39—C40 | 1.525 (4) |
C11—H11A | 0.9900 | C39—H39A | 0.9900 |
C11—H11B | 0.9900 | C39—H39B | 0.9900 |
C12—C13 | 1.523 (4) | C40—C41 | 1.530 (4) |
C12—H12A | 0.9900 | C40—H40A | 0.9900 |
C12—H12B | 0.9900 | C40—H40B | 0.9900 |
C13—C14 | 1.513 (4) | C41—C42 | 1.525 (4) |
C13—H13A | 0.9900 | C41—H41A | 0.9900 |
C13—H13B | 0.9900 | C41—H41B | 0.9900 |
C14—H14A | 0.9800 | C42—H42A | 0.9800 |
C14—H14B | 0.9800 | C42—H42B | 0.9800 |
C14—H14C | 0.9800 | C42—H42C | 0.9800 |
S3—C22 | 1.672 (3) | S7—C50 | 1.660 (3) |
S4—C22 | 1.742 (3) | S8—C50 | 1.750 (3) |
S4—C23 | 1.817 (3) | S8—C51 | 1.811 (3) |
O2—C15 | 1.344 (4) | O4—C43 | 1.343 (4) |
O2—H2O | 0.78 (3) | O4—H4O | 0.76 (3) |
N3—C21 | 1.278 (3) | N7—C49 | 1.280 (3) |
N3—N4 | 1.376 (3) | N7—N8 | 1.376 (3) |
N4—C22 | 1.336 (4) | N8—C50 | 1.334 (3) |
N4—H4N | 0.81 (3) | N8—H8N | 0.83 (3) |
C15—C16 | 1.397 (4) | C43—C44 | 1.388 (4) |
C15—C20 | 1.418 (4) | C43—C48 | 1.414 (4) |
C16—C17 | 1.363 (5) | C44—C45 | 1.364 (4) |
C16—H16 | 0.9500 | C44—H44 | 0.9500 |
C17—C18 | 1.385 (5) | C45—C46 | 1.391 (4) |
C17—H17 | 0.9500 | C45—H45 | 0.9500 |
C18—C19 | 1.381 (4) | C46—C47 | 1.384 (4) |
C18—H18 | 0.9500 | C46—H46 | 0.9500 |
C19—C20 | 1.395 (4) | C47—C48 | 1.399 (4) |
C19—H19 | 0.9500 | C47—H47 | 0.9500 |
C20—C21 | 1.456 (4) | C48—C49 | 1.453 (4) |
C21—H21 | 0.9500 | C49—H49 | 0.9500 |
C23—C24 | 1.513 (4) | C51—C52 | 1.517 (4) |
C23—H23A | 0.9900 | C51—H51A | 0.9900 |
C23—H23B | 0.9900 | C51—H51B | 0.9900 |
C24—C25 | 1.522 (4) | C52—C53 | 1.511 (4) |
C24—H24A | 0.9900 | C52—H52A | 0.9900 |
C24—H24B | 0.9900 | C52—H52B | 0.9900 |
C25—C26 | 1.521 (4) | C53—C54 | 1.529 (4) |
C25—H25A | 0.9900 | C53—H53A | 0.9900 |
C25—H25B | 0.9900 | C53—H53B | 0.9900 |
C26—C27 | 1.522 (4) | C54—C55 | 1.518 (4) |
C26—H26A | 0.9900 | C54—H54A | 0.9900 |
C26—H26B | 0.9900 | C54—H54B | 0.9900 |
C27—C28 | 1.515 (4) | C55—C56 | 1.509 (4) |
C27—H27A | 0.9900 | C55—H55A | 0.9900 |
C27—H27B | 0.9900 | C55—H55B | 0.9900 |
C28—H28A | 0.9800 | C56—H56A | 0.9800 |
C28—H28B | 0.9800 | C56—H56B | 0.9800 |
C28—H28C | 0.9800 | C56—H56C | 0.9800 |
C8—S2—C9 | 102.33 (13) | C36—S6—C37 | 102.60 (14) |
C1—O1—H1O | 119 (3) | C29—O3—H3O | 107 (2) |
C7—N1—N2 | 117.3 (2) | C35—N5—N6 | 116.9 (2) |
C8—N2—N1 | 121.4 (2) | C36—N6—N5 | 120.6 (2) |
C8—N2—H2N | 119.8 (19) | C36—N6—H6N | 118 (2) |
N1—N2—H2N | 118.8 (19) | N5—N6—H6N | 122 (2) |
O1—C1—C2 | 118.4 (3) | O3—C29—C30 | 118.0 (3) |
O1—C1—C6 | 122.3 (3) | O3—C29—C34 | 122.7 (3) |
C2—C1—C6 | 119.3 (3) | C30—C29—C34 | 119.3 (3) |
C3—C2—C1 | 120.4 (3) | C31—C30—C29 | 120.7 (3) |
C3—C2—H2 | 119.8 | C31—C30—H30 | 119.6 |
C1—C2—H2 | 119.8 | C29—C30—H30 | 119.6 |
C2—C3—C4 | 121.6 (3) | C30—C31—C32 | 121.6 (3) |
C2—C3—H3 | 119.2 | C30—C31—H31 | 119.2 |
C4—C3—H3 | 119.2 | C32—C31—H31 | 119.2 |
C3—C4—C5 | 118.9 (3) | C33—C32—C31 | 118.2 (3) |
C3—C4—H4 | 120.5 | C33—C32—H32 | 120.9 |
C5—C4—H4 | 120.5 | C31—C32—H32 | 120.9 |
C4—C5—C6 | 121.6 (3) | C32—C33—C34 | 121.9 (3) |
C4—C5—H5 | 119.2 | C32—C33—H33 | 119.0 |
C6—C5—H5 | 119.2 | C34—C33—H33 | 119.0 |
C5—C6—C1 | 118.2 (3) | C33—C34—C29 | 118.2 (3) |
C5—C6—C7 | 119.2 (3) | C33—C34—C35 | 119.5 (3) |
C1—C6—C7 | 122.6 (3) | C29—C34—C35 | 122.2 (3) |
N1—C7—C6 | 122.6 (3) | N5—C35—C34 | 121.2 (3) |
N1—C7—H7 | 118.7 | N5—C35—H35 | 119.4 |
C6—C7—H7 | 118.7 | C34—C35—H35 | 119.4 |
N2—C8—S1 | 120.6 (2) | N6—C36—S5 | 120.7 (2) |
N2—C8—S2 | 114.7 (2) | N6—C36—S6 | 114.1 (2) |
S1—C8—S2 | 124.79 (18) | S5—C36—S6 | 125.18 (18) |
C10—C9—S2 | 108.02 (19) | C38—C37—S6 | 107.53 (19) |
C10—C9—H9A | 110.1 | C38—C37—H37A | 110.2 |
S2—C9—H9A | 110.1 | S6—C37—H37A | 110.2 |
C10—C9—H9B | 110.1 | C38—C37—H37B | 110.2 |
S2—C9—H9B | 110.1 | S6—C37—H37B | 110.2 |
H9A—C9—H9B | 108.4 | H37A—C37—H37B | 108.5 |
C11—C10—C9 | 111.0 (2) | C37—C38—C39 | 112.0 (2) |
C11—C10—H10A | 109.4 | C37—C38—H38A | 109.2 |
C9—C10—H10A | 109.4 | C39—C38—H38A | 109.2 |
C11—C10—H10B | 109.4 | C37—C38—H38B | 109.2 |
C9—C10—H10B | 109.4 | C39—C38—H38B | 109.2 |
H10A—C10—H10B | 108.0 | H38A—C38—H38B | 107.9 |
C12—C11—C10 | 112.8 (2) | C38—C39—C40 | 112.0 (2) |
C12—C11—H11A | 109.0 | C38—C39—H39A | 109.2 |
C10—C11—H11A | 109.0 | C40—C39—H39A | 109.2 |
C12—C11—H11B | 109.0 | C38—C39—H39B | 109.2 |
C10—C11—H11B | 109.0 | C40—C39—H39B | 109.2 |
H11A—C11—H11B | 107.8 | H39A—C39—H39B | 107.9 |
C11—C12—C13 | 113.3 (2) | C39—C40—C41 | 113.3 (2) |
C11—C12—H12A | 108.9 | C39—C40—H40A | 108.9 |
C13—C12—H12A | 108.9 | C41—C40—H40A | 108.9 |
C11—C12—H12B | 108.9 | C39—C40—H40B | 108.9 |
C13—C12—H12B | 108.9 | C41—C40—H40B | 108.9 |
H12A—C12—H12B | 107.7 | H40A—C40—H40B | 107.7 |
C14—C13—C12 | 112.7 (2) | C42—C41—C40 | 112.7 (2) |
C14—C13—H13A | 109.0 | C42—C41—H41A | 109.1 |
C12—C13—H13A | 109.0 | C40—C41—H41A | 109.1 |
C14—C13—H13B | 109.0 | C42—C41—H41B | 109.1 |
C12—C13—H13B | 109.0 | C40—C41—H41B | 109.1 |
H13A—C13—H13B | 107.8 | H41A—C41—H41B | 107.8 |
C13—C14—H14A | 109.5 | C41—C42—H42A | 109.5 |
C13—C14—H14B | 109.5 | C41—C42—H42B | 109.5 |
H14A—C14—H14B | 109.5 | H42A—C42—H42B | 109.5 |
C13—C14—H14C | 109.5 | C41—C42—H42C | 109.5 |
H14A—C14—H14C | 109.5 | H42A—C42—H42C | 109.5 |
H14B—C14—H14C | 109.5 | H42B—C42—H42C | 109.5 |
C22—S4—C23 | 102.46 (15) | C50—S8—C51 | 102.66 (13) |
C15—O2—H2O | 119 (3) | C43—O4—H4O | 109 (3) |
C21—N3—N4 | 116.7 (3) | C49—N7—N8 | 117.1 (2) |
C22—N4—N3 | 121.1 (3) | C50—N8—N7 | 120.7 (2) |
C22—N4—H4N | 119 (2) | C50—N8—H8N | 120 (2) |
N3—N4—H4N | 120 (2) | N7—N8—H8N | 119 (2) |
O2—C15—C16 | 117.9 (3) | O4—C43—C44 | 117.8 (3) |
O2—C15—C20 | 122.8 (3) | O4—C43—C48 | 123.1 (3) |
C16—C15—C20 | 119.2 (3) | C44—C43—C48 | 119.1 (3) |
C17—C16—C15 | 120.1 (3) | C45—C44—C43 | 121.0 (3) |
C17—C16—H16 | 119.9 | C45—C44—H44 | 119.5 |
C15—C16—H16 | 119.9 | C43—C44—H44 | 119.5 |
C16—C17—C18 | 122.2 (3) | C44—C45—C46 | 121.5 (3) |
C16—C17—H17 | 118.9 | C44—C45—H45 | 119.3 |
C18—C17—H17 | 118.9 | C46—C45—H45 | 119.3 |
C19—C18—C17 | 118.1 (3) | C47—C46—C45 | 118.2 (3) |
C19—C18—H18 | 120.9 | C47—C46—H46 | 120.9 |
C17—C18—H18 | 120.9 | C45—C46—H46 | 120.9 |
C18—C19—C20 | 122.0 (3) | C46—C47—C48 | 121.8 (3) |
C18—C19—H19 | 119.0 | C46—C47—H47 | 119.1 |
C20—C19—H19 | 119.0 | C48—C47—H47 | 119.1 |
C19—C20—C15 | 118.4 (3) | C47—C48—C43 | 118.6 (3) |
C19—C20—C21 | 119.4 (3) | C47—C48—C49 | 118.9 (3) |
C15—C20—C21 | 122.2 (3) | C43—C48—C49 | 122.5 (3) |
N3—C21—C20 | 122.3 (3) | N7—C49—C48 | 120.8 (3) |
N3—C21—H21 | 118.9 | N7—C49—H49 | 119.6 |
C20—C21—H21 | 118.9 | C48—C49—H49 | 119.6 |
N4—C22—S3 | 120.7 (2) | N8—C50—S7 | 121.0 (2) |
N4—C22—S4 | 114.4 (2) | N8—C50—S8 | 113.9 (2) |
S3—C22—S4 | 124.8 (2) | S7—C50—S8 | 125.07 (17) |
C24—C23—S4 | 108.4 (2) | C52—C51—S8 | 107.84 (19) |
C24—C23—H23A | 110.0 | C52—C51—H51A | 110.1 |
S4—C23—H23A | 110.0 | S8—C51—H51A | 110.1 |
C24—C23—H23B | 110.0 | C52—C51—H51B | 110.1 |
S4—C23—H23B | 110.0 | S8—C51—H51B | 110.1 |
H23A—C23—H23B | 108.4 | H51A—C51—H51B | 108.5 |
C23—C24—C25 | 110.9 (2) | C53—C52—C51 | 112.2 (2) |
C23—C24—H24A | 109.5 | C53—C52—H52A | 109.2 |
C25—C24—H24A | 109.5 | C51—C52—H52A | 109.2 |
C23—C24—H24B | 109.5 | C53—C52—H52B | 109.2 |
C25—C24—H24B | 109.5 | C51—C52—H52B | 109.2 |
H24A—C24—H24B | 108.1 | H52A—C52—H52B | 107.9 |
C26—C25—C24 | 113.5 (2) | C52—C53—C54 | 112.9 (2) |
C26—C25—H25A | 108.9 | C52—C53—H53A | 109.0 |
C24—C25—H25A | 108.9 | C54—C53—H53A | 109.0 |
C26—C25—H25B | 108.9 | C52—C53—H53B | 109.0 |
C24—C25—H25B | 108.9 | C54—C53—H53B | 109.0 |
H25A—C25—H25B | 107.7 | H53A—C53—H53B | 107.8 |
C25—C26—C27 | 113.0 (3) | C55—C54—C53 | 113.4 (2) |
C25—C26—H26A | 109.0 | C55—C54—H54A | 108.9 |
C27—C26—H26A | 109.0 | C53—C54—H54A | 108.9 |
C25—C26—H26B | 109.0 | C55—C54—H54B | 108.9 |
C27—C26—H26B | 109.0 | C53—C54—H54B | 108.9 |
H26A—C26—H26B | 107.8 | H54A—C54—H54B | 107.7 |
C28—C27—C26 | 113.2 (3) | C56—C55—C54 | 112.9 (2) |
C28—C27—H27A | 108.9 | C56—C55—H55A | 109.0 |
C26—C27—H27A | 108.9 | C54—C55—H55A | 109.0 |
C28—C27—H27B | 108.9 | C56—C55—H55B | 109.0 |
C26—C27—H27B | 108.9 | C54—C55—H55B | 109.0 |
H27A—C27—H27B | 107.8 | H55A—C55—H55B | 107.8 |
C27—C28—H28A | 109.5 | C55—C56—H56A | 109.5 |
C27—C28—H28B | 109.5 | C55—C56—H56B | 109.5 |
H28A—C28—H28B | 109.5 | H56A—C56—H56B | 109.5 |
C27—C28—H28C | 109.5 | C55—C56—H56C | 109.5 |
H28A—C28—H28C | 109.5 | H56A—C56—H56C | 109.5 |
H28B—C28—H28C | 109.5 | H56B—C56—H56C | 109.5 |
C7—N1—N2—C8 | −177.6 (2) | C35—N5—N6—C36 | 176.3 (2) |
O1—C1—C2—C3 | 179.9 (3) | O3—C29—C30—C31 | 179.3 (3) |
C6—C1—C2—C3 | −0.4 (4) | C34—C29—C30—C31 | −1.3 (4) |
C1—C2—C3—C4 | 0.2 (5) | C29—C30—C31—C32 | 1.8 (5) |
C2—C3—C4—C5 | 0.1 (5) | C30—C31—C32—C33 | −1.2 (5) |
C3—C4—C5—C6 | −0.1 (5) | C31—C32—C33—C34 | 0.1 (4) |
C4—C5—C6—C1 | −0.1 (4) | C32—C33—C34—C29 | 0.5 (4) |
C4—C5—C6—C7 | 177.1 (3) | C32—C33—C34—C35 | −176.3 (3) |
O1—C1—C6—C5 | −180.0 (3) | O3—C29—C34—C33 | 179.5 (2) |
C2—C1—C6—C5 | 0.4 (4) | C30—C29—C34—C33 | 0.1 (4) |
O1—C1—C6—C7 | 2.9 (4) | O3—C29—C34—C35 | −3.8 (4) |
C2—C1—C6—C7 | −176.8 (3) | C30—C29—C34—C35 | 176.8 (2) |
N2—N1—C7—C6 | 178.5 (2) | N6—N5—C35—C34 | −178.1 (2) |
C5—C6—C7—N1 | −178.3 (3) | C33—C34—C35—N5 | 179.0 (2) |
C1—C6—C7—N1 | −1.2 (4) | C29—C34—C35—N5 | 2.3 (4) |
N1—N2—C8—S1 | 179.09 (18) | N5—N6—C36—S5 | −178.17 (19) |
N1—N2—C8—S2 | −1.0 (3) | N5—N6—C36—S6 | 2.1 (3) |
C9—S2—C8—N2 | −174.8 (2) | C37—S6—C36—N6 | 174.1 (2) |
C9—S2—C8—S1 | 5.1 (2) | C37—S6—C36—S5 | −5.6 (2) |
C8—S2—C9—C10 | 177.90 (19) | C36—S6—C37—C38 | −179.37 (19) |
S2—C9—C10—C11 | −179.99 (19) | S6—C37—C38—C39 | −178.21 (19) |
C9—C10—C11—C12 | −179.2 (2) | C37—C38—C39—C40 | 179.3 (2) |
C10—C11—C12—C13 | 175.8 (2) | C38—C39—C40—C41 | −178.6 (2) |
C11—C12—C13—C14 | −179.8 (2) | C39—C40—C41—C42 | 176.4 (2) |
C21—N3—N4—C22 | 178.1 (3) | C49—N7—N8—C50 | −176.6 (2) |
O2—C15—C16—C17 | 179.7 (3) | O4—C43—C44—C45 | −179.9 (3) |
C20—C15—C16—C17 | 0.1 (4) | C48—C43—C44—C45 | −0.1 (4) |
C15—C16—C17—C18 | 1.0 (5) | C43—C44—C45—C46 | −0.1 (5) |
C16—C17—C18—C19 | −1.5 (5) | C44—C45—C46—C47 | −0.2 (4) |
C17—C18—C19—C20 | 1.0 (5) | C45—C46—C47—C48 | 0.7 (4) |
C18—C19—C20—C15 | 0.1 (4) | C46—C47—C48—C43 | −0.8 (4) |
C18—C19—C20—C21 | −178.0 (3) | C46—C47—C48—C49 | 176.6 (2) |
O2—C15—C20—C19 | 179.8 (3) | O4—C43—C48—C47 | −179.7 (2) |
C16—C15—C20—C19 | −0.6 (4) | C44—C43—C48—C47 | 0.5 (4) |
O2—C15—C20—C21 | −2.2 (4) | O4—C43—C48—C49 | 3.0 (4) |
C16—C15—C20—C21 | 177.4 (3) | C44—C43—C48—C49 | −176.8 (2) |
N4—N3—C21—C20 | −177.6 (2) | N8—N7—C49—C48 | 178.1 (2) |
C19—C20—C21—N3 | 179.1 (3) | C47—C48—C49—N7 | −179.3 (2) |
C15—C20—C21—N3 | 1.1 (4) | C43—C48—C49—N7 | −1.9 (4) |
N3—N4—C22—S3 | −179.53 (19) | N7—N8—C50—S7 | 176.98 (18) |
N3—N4—C22—S4 | 0.6 (4) | N7—N8—C50—S8 | −3.4 (3) |
C23—S4—C22—N4 | 175.2 (2) | C51—S8—C50—N8 | −174.4 (2) |
C23—S4—C22—S3 | −4.7 (2) | C51—S8—C50—S7 | 5.2 (2) |
C22—S4—C23—C24 | 178.7 (2) | C50—S8—C51—C52 | −176.75 (19) |
S4—C23—C24—C25 | −178.71 (19) | S8—C51—C52—C53 | 177.41 (19) |
C23—C24—C25—C26 | 176.4 (2) | C51—C52—C53—C54 | −176.9 (2) |
C24—C25—C26—C27 | −175.7 (2) | C52—C53—C54—C55 | 179.5 (2) |
C25—C26—C27—C28 | −178.6 (3) | C53—C54—C55—C56 | −177.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.73 (3) | 2.13 (3) | 2.684 (3) | 135 (3) |
O2—H2O···N3 | 0.78 (3) | 2.09 (3) | 2.685 (3) | 133 (3) |
O3—H3O···N5 | 0.84 (3) | 1.91 (3) | 2.662 (3) | 148 (3) |
O4—H4O···N7 | 0.75 (3) | 2.00 (3) | 2.663 (3) | 146 (3) |
N2—H2N···S7i | 0.86 (3) | 2.58 (3) | 3.430 (3) | 169 (3) |
N4—H4N···S3ii | 0.81 (3) | 2.64 (3) | 3.439 (3) | 171 (2) |
N6—H6N···S5iii | 0.84 (3) | 2.59 (3) | 3.398 (3) | 162 (2) |
N8—H8N···S1iv | 0.83 (3) | 2.61 (3) | 3.403 (3) | 160 (2) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.73 (3) | 2.13 (3) | 2.684 (3) | 135 (3) |
O2—H2O···N3 | 0.78 (3) | 2.09 (3) | 2.685 (3) | 133 (3) |
O3—H3O···N5 | 0.84 (3) | 1.91 (3) | 2.662 (3) | 148 (3) |
O4—H4O···N7 | 0.75 (3) | 2.00 (3) | 2.663 (3) | 146 (3) |
N2—H2N···S7i | 0.86 (3) | 2.58 (3) | 3.430 (3) | 169 (3) |
N4—H4N···S3ii | 0.81 (3) | 2.64 (3) | 3.439 (3) | 171 (2) |
N6—H6N···S5iii | 0.84 (3) | 2.59 (3) | 3.398 (3) | 162 (2) |
N8—H8N···S1iv | 0.83 (3) | 2.61 (3) | 3.403 (3) | 160 (2) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H20N2OS2 |
Mr | 296.44 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 173 |
a, b, c (Å) | 18.9744 (4), 16.0269 (3), 21.1146 (4) |
β (°) | 100.808 (1) |
V (Å3) | 6307.1 (2) |
Z | 16 |
Radiation type | Cu Kα |
µ (mm−1) | 3.01 |
Crystal size (mm) | 0.50 × 0.35 × 0.34 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10367, 10367, 6152 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.581 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.176, 0.93 |
No. of reflections | 10367 |
No. of parameters | 713 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.01, −0.46 |
Computer programs: RAPID-AUTO (Rigaku, 2001), SIR92 (Altomare et al., 1994), SHELXL2014 (Sheldrick, 2015), CrystalStructure (Rigaku, 2010).
Acknowledgements
MBHH and MSB are grateful to the Department of Chemistry, Rajshahi University, for the provision of laboratory facilities. MCS acknowledges the Department of Applied Chemistry,Toyama University, for providing funds for single-crystal X-ray analyses.
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