research communications
E)-(2-hydroxy-3-methoxybenzylidene)amino]-1-methyl-1-phenylthiourea
of 3-[(aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India, bDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
*Correspondence e-mail: ksethusankar@yahoo.co.in
In the 16H17N3O2S, there are two independent molecules (A and B), which show an E conformation with respect to the C=N bond. An intramolecular O—H⋯N hydrogen bond with an S(6) motif stabilizes the molecular structure. The terminal phenyl and benzene rings are almost orthogonal to each other, the dihedral angle being 87.47 (13)° for molecule A and 89.86 (17)° for molecule B. In the crystal, weak bifurcated N—H⋯(O,O) hydrogen bonds link the two independent molecules, forming a supramolecular chain with a C21(14)[R21(5)] motif along the b axis. A weak C—H⋯O interaction is also observed in the chain.
of the title compound, CKeywords: crystal structure; hydrazinecarbothioamide; thiourea derivatives; α-N-heterocyclic; hydrogen bonding.
CCDC reference: 1435114
1. Chemical context
Thiosemicarbazones have emerged as an important class of S- and N-containing ligands due to their propensity to react with a wide range of metals (Casas et al., 2000) and their broad spectrum of chemotherapeutic properties (Quiroga et al., 1998). Their structural diversity is due to their variable coordinative abilities (Sreekanth et al., 2004), arising from thioamido–thioiminol Thiosemicarbazones usually act as chelating ligands for metal ions through sulfur (=S) and azomethane (=N—) groups, though in some cases they behave as monodentate ligands through the sulfur (=S) only. They are also important intermediates for obtaining heterocylic rings such as thiazolidones, oxadiazoles, pyrazolidones and thiadiazoles (Greenbaum et al., 2004; Küçükgüzel et al., 2006). As a result of their long chain structure, they are very flexible and form linkages with a variety of metal ions. They have also been used for the analysis of metals and in device applications related to telecommunications, optical computing and optical information processing (Tian et al., 1997).
2. Structural commentary
The A and B) with almost identical conformations. The hydrazine carbothioamide backbone is nearly planar with a maximum deviation of 0.023 (2) Å at atom N2 for molecule A and of 0.054 (2) Å at atom N2′ for B. The closeness of the C=S bond lengths [C9—S1 = 1.666 (2) Å and C9′—S1′ = 1.657 (2) Å] to the expected distance (1.60 Å; Allen et al., 1987; Seena et al., 2008) indicates that the compound exists in the thione form. This is further confirmed by the N—N and N—C bond lengths (Gangadharan et al., 2015). The bond lengths in the N—C(=S)—N fragments indicate π delocalization due to the fact that the C—N and C—S bonds are shorter than typical single bonds (ca 1.47 and 1.73 Å, respectively) and longer than corresponding double bonds (ca 1.29 and 1.55 Å, respectively; Casas et al., 2000; Tenório et al. 2005). The terminal phenyl and benzene rings are almost orthogonal to each other, with a dihedral angle of 87.47 (13)° for A and 89.86 (17)° for B. In each molecule (A and B), an intramolecular O—H⋯N interaction (Table 1) with an S(6) ring motif stabilizes the molecular structure (Fig. 1).
of the compound comprises two independent molecules (3. Supramolecular features
In the crystal, intermolecular bifurcated hydrogen bonds (N2—H2⋯O1′i, N2—H2⋯O2′i, N2′—H2′⋯O1 and N2′—H2′⋯O2; symmetry code: (i) x, −1 + y, z] with (5) ring motifs interlink adjacent independent molecules, resulting in a supramolecular chain with a (14)[(5)] motif along the b axis. An intermolecular C—H⋯O interaction is also observed within the chain (Fig. 2).
4. Database survey
A search of Cambridge Structural Database (Version 5.36; last updated Nov. 2014; Groom & Allen, 2014) showed three closely related structures with pyridine-2-carbaldehyde thiosemicarbazones, differing from the title compound only in the presence of one or more pyridyl groups instead of the substituted phenyl group. Two of these, namely, (E)-4-methyl-4-phenyl-1-(2-pyridylmethylene)-3-thiosemicarbazide (Rapheal et al., 2007) and di-2-pyridyl ketone 4-methyl-4-phenylthosemicarbazone (Philip et al., 2004) crystallize in the same P of the title compound. The third compound, 2-benzoyl pyridine-N-methyl-N-phenylthiosemicarbazone, crystallizes in P21/n. The similarity in bond lengths along the hydrazine carbothioamide moieties and shortening of the C—N single bonds from the normal value (ca 1.48 Å) indicate some degree of delocalization in the compounds. The C=S bond lengths in all compared compounds lie in the range 1.66–1.67 Å, intermediate between S—Csp2 and S=Csp2 bond lengths (ca 1.75 and 1.59 Å, respectively), showing a partial double-bond character. Similar bond lengths for the C=S bond have also been observed in hydrazine carbothioamide derivatives (Gangadharan et al., 2014, 2015; Vimala et al., 2014). The partial double-bond nature of the C=S bond is a feature in the compared hydrazine carbothioamide derivatives, irrespective of the substituents.
5. Synthesis and crystallization
1.81 g (0.01 mol) of N-methyl-N-phenylhydrazine carbothioamide was dissolved in 20 ml of hot methanol and to this was added 1.52 g (0.01 mol) of 2-hydroxy-3-methoxybenzaldehyde in 10 ml of ethanol over a period of 10 min with continuous stirring. The reaction mixture was refluxed for 2 h and allowed to cool whereby a shining yellow compound began to separate. This was filtered and washed thoroughly with ethanol and then dried in vacuum. The compound was recrystallized from a hot ethanol solution, giving colourless block-like crystals (yield 91%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of an ethanol solution at room temperature.
6. Refinement
Crystal data, data collection and structure . H atoms were localized in a difference-Fourier map. H atoms bound to O and N atoms were refined freely; refined distances O—H = 0.79 (3) and 0.87 (3) Å, and N—H = 0.80 (2) and 0.83 (2) Å. C-bound H atoms were treated as riding, with C—H = 0.93 or 0.96 Å, and with Uiso(H) = 1.2Ueq(C) for aromatic and 1.5Ueq(C) for methyl groups. The rotation angles for methyl groups were optimized.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1435114
10.1107/S2056989016005326/is5446sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016005326/is5446Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016005326/is5446Isup3.cml
Thiosemicarbazones have emerged as an important class of S- and N-containing ligands due to their propensity to react with a wide range of metals (Casas et al., 2000) and their broad spectrum of chemotherapeutic properties (Quiroga et al., 1998). Their structural diversity is due to their variable coordinative abilities (Sreekanth et al., 2004), arising from thioamido–thioiminol ═S) and azomethane (═N–) groups, though in some cases they behave as monodentate ligands through the sulfur (═S) only. They are also important intermediates for obtaining heterocylic rings such as thiazolidones, oxadiazoles, pyrazolidones and thiadiazoles (Greenbaum et al., 2004; Küçükgüzel et al., 2006). As a result of their long chain structure, they are very flexible and form linkages with a variety of metal ions. They have also been used for the analysis of metals and in device applications related to telecommunications, optical computing and optical information processing (Tian et al., 1997).
Thiosemicarbazones usually act as chelating ligands for metal ions through sulfur (The ═S bond lengths [C9—S1 = 1.666 (2) Å and C9'—S1' = 1.657 (2) Å] to the expected distance (1.60 Å; Allen et al., 1987; Seena et al., 2008) indicates that the compound exists in the thione form. This is further confirmed by the N—N and N—C bond lengths (Gangadharan et al., 2015). The bond lengths in the N—C(═ S)—N fragments indicate π delocalization due to the fact that the C—N and C—S bonds are shorter than typical single bonds (ca 1.47 and 1.73 Å, respectively) and longer than corresponding double bonds (ca 1.29 and 1.55 Å, respectively; Casas et al., 2000; Tenório et al. 2005). The terminal phenyl and benzene rings are almost orthogonal to each other, with a dihedral angle of 87.47 (13)° for A and 89.86 (17)° for B. In each molecule (A and B), an intramolecular O—H···N interaction (Table 1) with an S(6) ring motif stabilizes the molecular structure (Fig. 1).
of the compound comprises two independent molecules (A and B) with almost identical conformations. The hydrazine carbothioamide backbone is nearly planar with a maximum deviation of 0.023 (2) Å at atom N2 for molecule A and of 0.054 (2) Å at atom N2' for B. The closeness of the CIn the crystal, intermolecular bifurcated hydrogen bonds (N2—H2···O1'i, N2—H2···O2'i, N2'—H2'···O1 and N2'—H2'···O2; symmetry code: (i) x, -1 + y, z] with R21(5) ring motifs interlink adjacent independent molecules, resulting in a supramolecular chain with a C21(14)[R21(5)] motif along the b axis. An intermolecular C—H···O interaction is also observed within the chain (Fig. 2).
A search of Cambridge Structural Database (Version 5.36; last updated Nov. 2014; Groom & Allen, 2014) showed three closely related structures with pyridine-2-carbaldehyde thiosemicarbazones, differing from the title compound only in the presence of one or more pyridyl groups instead of the substituted phenyl group. Two of these, namely, (E)-4-methyl-4-phenyl-1-(2-pyridylmethylene)-3-thiosemicarbazide (Rapheal et al., 2007) and di-2-pyridyl ketone 4-methyl-4-phenylthosemicarbazone (Philip et al., 2004) crystallize in the same P1 of the title compound. The third compound, 2-benzoyl pyridine-N-methyl-N-phenylthiosemicarbazone, crystallizes in P21/n. The similarity in bond lengths along the hydrazine carbothioamide moieties and shortening of the C—N single bonds from the normal value (ca 1.48 Å) indicate some degree of delocalization in the compounds. The C═S bond lengths in all compared compounds lie in the range 1.66–1.67 Å, intermediate between S—Csp2 and S═Csp2 bond lengths (ca 1.75 and 1.59 Å, respectively), showing a partial double-bond character. Similar bond lengths for the C═S bond have also been observed in hydrazine carbothioamide derivatives (Gangadharan et al., 2014, 2015; Vimala et al., 2014). The partial double-bond nature of the C═ S bond is a feature in the compared hydrazine carbothioamide derivatives, irrespective of the substituents.
1.81 g (0.01 mol) of N-methyl-N-phenylhydrazine carbothioamide was dissolved in 20 ml of hot methanol and to this was added 1.52 g (0.01 mol) of 2-hydroxy-3-methoxybenzaldehyde in 10 ml of ethanol over a period of 10 min with continuous stirring. The reaction mixture was refluxed for 2 h and allowed to cool whereby a shining yellow compound began to separate. This was filtered and washed thoroughly with ethanol and then dried in vacuum. The compound was recrystallized from a hot ethanol solution, giving colourless block-like crystals (yield 91%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of an ethanol solution at room temperature.
Crystal data, data collection and structure
details are summarized in Table 2. H atoms were localized in a difference-Fourier map. H atoms bound to O and N atoms were refined freely; refined distances O—H = 0.79 (3) and 0.87 (3) Å, and N—H = 0.80 (2) and 0.83 (2) Å. C-bound H atoms were treated as riding, with C—H = 0.93 or 0.96 Å, and with Uiso(H) = 1.2Ueq(C) for aromatic and 1.5Ueq(C) for methyl groups. The rotation angles for methyl groups were optimized.Thiosemicarbazones have emerged as an important class of S- and N-containing ligands due to their propensity to react with a wide range of metals (Casas et al., 2000) and their broad spectrum of chemotherapeutic properties (Quiroga et al., 1998). Their structural diversity is due to their variable coordinative abilities (Sreekanth et al., 2004), arising from thioamido–thioiminol ═S) and azomethane (═N–) groups, though in some cases they behave as monodentate ligands through the sulfur (═S) only. They are also important intermediates for obtaining heterocylic rings such as thiazolidones, oxadiazoles, pyrazolidones and thiadiazoles (Greenbaum et al., 2004; Küçükgüzel et al., 2006). As a result of their long chain structure, they are very flexible and form linkages with a variety of metal ions. They have also been used for the analysis of metals and in device applications related to telecommunications, optical computing and optical information processing (Tian et al., 1997).
Thiosemicarbazones usually act as chelating ligands for metal ions through sulfur (The ═S bond lengths [C9—S1 = 1.666 (2) Å and C9'—S1' = 1.657 (2) Å] to the expected distance (1.60 Å; Allen et al., 1987; Seena et al., 2008) indicates that the compound exists in the thione form. This is further confirmed by the N—N and N—C bond lengths (Gangadharan et al., 2015). The bond lengths in the N—C(═ S)—N fragments indicate π delocalization due to the fact that the C—N and C—S bonds are shorter than typical single bonds (ca 1.47 and 1.73 Å, respectively) and longer than corresponding double bonds (ca 1.29 and 1.55 Å, respectively; Casas et al., 2000; Tenório et al. 2005). The terminal phenyl and benzene rings are almost orthogonal to each other, with a dihedral angle of 87.47 (13)° for A and 89.86 (17)° for B. In each molecule (A and B), an intramolecular O—H···N interaction (Table 1) with an S(6) ring motif stabilizes the molecular structure (Fig. 1).
of the compound comprises two independent molecules (A and B) with almost identical conformations. The hydrazine carbothioamide backbone is nearly planar with a maximum deviation of 0.023 (2) Å at atom N2 for molecule A and of 0.054 (2) Å at atom N2' for B. The closeness of the CIn the crystal, intermolecular bifurcated hydrogen bonds (N2—H2···O1'i, N2—H2···O2'i, N2'—H2'···O1 and N2'—H2'···O2; symmetry code: (i) x, -1 + y, z] with R21(5) ring motifs interlink adjacent independent molecules, resulting in a supramolecular chain with a C21(14)[R21(5)] motif along the b axis. An intermolecular C—H···O interaction is also observed within the chain (Fig. 2).
A search of Cambridge Structural Database (Version 5.36; last updated Nov. 2014; Groom & Allen, 2014) showed three closely related structures with pyridine-2-carbaldehyde thiosemicarbazones, differing from the title compound only in the presence of one or more pyridyl groups instead of the substituted phenyl group. Two of these, namely, (E)-4-methyl-4-phenyl-1-(2-pyridylmethylene)-3-thiosemicarbazide (Rapheal et al., 2007) and di-2-pyridyl ketone 4-methyl-4-phenylthosemicarbazone (Philip et al., 2004) crystallize in the same P1 of the title compound. The third compound, 2-benzoyl pyridine-N-methyl-N-phenylthiosemicarbazone, crystallizes in P21/n. The similarity in bond lengths along the hydrazine carbothioamide moieties and shortening of the C—N single bonds from the normal value (ca 1.48 Å) indicate some degree of delocalization in the compounds. The C═S bond lengths in all compared compounds lie in the range 1.66–1.67 Å, intermediate between S—Csp2 and S═Csp2 bond lengths (ca 1.75 and 1.59 Å, respectively), showing a partial double-bond character. Similar bond lengths for the C═S bond have also been observed in hydrazine carbothioamide derivatives (Gangadharan et al., 2014, 2015; Vimala et al., 2014). The partial double-bond nature of the C═ S bond is a feature in the compared hydrazine carbothioamide derivatives, irrespective of the substituents.
1.81 g (0.01 mol) of N-methyl-N-phenylhydrazine carbothioamide was dissolved in 20 ml of hot methanol and to this was added 1.52 g (0.01 mol) of 2-hydroxy-3-methoxybenzaldehyde in 10 ml of ethanol over a period of 10 min with continuous stirring. The reaction mixture was refluxed for 2 h and allowed to cool whereby a shining yellow compound began to separate. This was filtered and washed thoroughly with ethanol and then dried in vacuum. The compound was recrystallized from a hot ethanol solution, giving colourless block-like crystals (yield 91%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of an ethanol solution at room temperature.
detailsCrystal data, data collection and structure
details are summarized in Table 2. H atoms were localized in a difference-Fourier map. H atoms bound to O and N atoms were refined freely; refined distances O—H = 0.79 (3) and 0.87 (3) Å, and N—H = 0.80 (2) and 0.83 (2) Å. C-bound H atoms were treated as riding, with C—H = 0.93 or 0.96 Å, and with Uiso(H) = 1.2Ueq(C) for aromatic and 1.5Ueq(C) for methyl groups. The rotation angles for methyl groups were optimized.Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate the intramolecular O—H···N interactions. | |
Fig. 2. A packing diagram of the compound viewed along the c axis, showing the N—H···O and C—H···O hydrogen bonds (dashed lines). H atoms not involved in the hydrogen bonds have been omitted for clarity. |
C16H17N3O2S | Z = 4 |
Mr = 315.39 | F(000) = 664 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6869 (2) Å | Cell parameters from 6781 reflections |
b = 12.6140 (2) Å | θ = 1.4–26.5° |
c = 14.7498 (3) Å | µ = 0.21 mm−1 |
α = 77.839 (1)° | T = 296 K |
β = 76.5330 (9)° | Block, colourless |
γ = 70.875 (1)° | 0.35 × 0.30 × 0.25 mm |
V = 1638.19 (5) Å3 |
Bruker APEXII CCD diffractometer | 6781 independent reflections |
Radiation source: fine-focus sealed tube | 5047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω & φ scans | θmax = 26.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.931, Tmax = 0.950 | k = −15→15 |
24246 measured reflections | l = −18→18 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.4596P] where P = (Fo2 + 2Fc2)/3 |
6781 reflections | (Δ/σ)max = 0.01 |
417 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C16H17N3O2S | γ = 70.875 (1)° |
Mr = 315.39 | V = 1638.19 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6869 (2) Å | Mo Kα radiation |
b = 12.6140 (2) Å | µ = 0.21 mm−1 |
c = 14.7498 (3) Å | T = 296 K |
α = 77.839 (1)° | 0.35 × 0.30 × 0.25 mm |
β = 76.5330 (9)° |
Bruker APEXII CCD diffractometer | 6781 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5047 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.950 | Rint = 0.026 |
24246 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.30 e Å−3 |
6781 reflections | Δρmin = −0.30 e Å−3 |
417 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1' | 0.52668 (19) | 0.69280 (15) | 0.27874 (12) | 0.0439 (4) | |
C2' | 0.4045 (2) | 0.78361 (16) | 0.30538 (13) | 0.0490 (4) | |
C3' | 0.2620 (2) | 0.77780 (19) | 0.31481 (15) | 0.0601 (5) | |
H3' | 0.1812 | 0.8388 | 0.3322 | 0.072* | |
C4' | 0.2396 (2) | 0.6813 (2) | 0.29845 (17) | 0.0648 (6) | |
H4' | 0.1434 | 0.6777 | 0.3045 | 0.078* | |
C5' | 0.3575 (2) | 0.59107 (18) | 0.27348 (15) | 0.0573 (5) | |
H5' | 0.3409 | 0.5262 | 0.2636 | 0.069* | |
C6' | 0.50335 (19) | 0.59539 (15) | 0.26260 (13) | 0.0452 (4) | |
C7' | 0.3237 (3) | 0.9658 (2) | 0.3546 (2) | 0.0872 (8) | |
H7'1 | 0.2570 | 0.9977 | 0.3103 | 0.131* | |
H7'2 | 0.3639 | 1.0227 | 0.3627 | 0.131* | |
H7'3 | 0.2709 | 0.9393 | 0.4140 | 0.131* | |
C8' | 0.6264 (2) | 0.49832 (17) | 0.23490 (14) | 0.0520 (5) | |
H8' | 0.6081 | 0.4347 | 0.2237 | 0.062* | |
C9' | 1.0115 (2) | 0.39863 (17) | 0.21247 (16) | 0.0578 (5) | |
N3' | 1.11972 (19) | 0.31302 (16) | 0.17464 (16) | 0.0719 (5) | |
C11' | 1.2715 (3) | 0.2825 (2) | 0.1928 (2) | 0.0885 (8) | |
H11A | 1.3240 | 0.3305 | 0.1493 | 0.133* | |
H11B | 1.3216 | 0.2048 | 0.1847 | 0.133* | |
H11C | 1.2683 | 0.2923 | 0.2561 | 0.133* | |
C12' | 1.0977 (2) | 0.25550 (19) | 0.1077 (2) | 0.0702 (6) | |
C13' | 1.0959 (4) | 0.3065 (3) | 0.0157 (3) | 0.0978 (9) | |
H13' | 1.1060 | 0.3792 | −0.0019 | 0.117* | |
C14' | 1.0793 (4) | 0.2515 (4) | −0.0510 (3) | 0.1310 (14) | |
H14' | 1.0777 | 0.2863 | −0.1131 | 0.157* | |
C15' | 1.0655 (5) | 0.1448 (5) | −0.0232 (5) | 0.162 (2) | |
H15' | 1.0570 | 0.1057 | −0.0675 | 0.194* | |
C16' | 1.0638 (6) | 0.0947 (4) | 0.0671 (5) | 0.158 (2) | |
H16' | 1.0513 | 0.0227 | 0.0845 | 0.189* | |
C17' | 1.0805 (3) | 0.1495 (2) | 0.1346 (3) | 0.1067 (11) | |
H17' | 1.0799 | 0.1146 | 0.1968 | 0.128* | |
N1' | 0.75880 (17) | 0.50090 (14) | 0.22614 (13) | 0.0557 (4) | |
N2' | 0.87327 (19) | 0.40950 (16) | 0.19792 (15) | 0.0643 (5) | |
O1' | 0.66301 (16) | 0.70549 (13) | 0.27051 (11) | 0.0575 (4) | |
O2' | 0.44044 (16) | 0.87408 (12) | 0.32031 (12) | 0.0663 (4) | |
S1' | 1.04243 (7) | 0.48414 (6) | 0.27171 (5) | 0.0765 (2) | |
C1 | 0.67203 (19) | 0.19526 (15) | 0.12355 (13) | 0.0455 (4) | |
C2 | 0.6581 (2) | 0.28011 (17) | 0.04616 (15) | 0.0573 (5) | |
C3 | 0.6084 (3) | 0.2679 (2) | −0.02991 (17) | 0.0795 (7) | |
H3 | 0.5993 | 0.3251 | −0.0814 | 0.095* | |
C4 | 0.5719 (4) | 0.1714 (3) | −0.03010 (19) | 0.0966 (10) | |
H4 | 0.5370 | 0.1638 | −0.0813 | 0.116* | |
C5 | 0.5870 (3) | 0.0870 (2) | 0.04473 (17) | 0.0808 (8) | |
H5 | 0.5625 | 0.0219 | 0.0439 | 0.097* | |
C6 | 0.6382 (2) | 0.09610 (16) | 0.12254 (13) | 0.0495 (4) | |
C7 | 0.7106 (4) | 0.4531 (3) | −0.0295 (2) | 0.1088 (11) | |
H7A | 0.7793 | 0.4152 | −0.0793 | 0.163* | |
H7B | 0.7463 | 0.5101 | −0.0169 | 0.163* | |
H7C | 0.6154 | 0.4881 | −0.0483 | 0.163* | |
C8 | 0.6577 (2) | 0.00218 (17) | 0.19840 (14) | 0.0533 (5) | |
H8 | 0.6352 | −0.0631 | 0.1951 | 0.064* | |
C9 | 0.8143 (2) | −0.08626 (16) | 0.40086 (13) | 0.0493 (4) | |
N3 | 0.8251 (2) | −0.17535 (15) | 0.47095 (12) | 0.0591 (4) | |
C11 | 0.9338 (3) | −0.2017 (2) | 0.53275 (16) | 0.0704 (6) | |
H11D | 1.0322 | −0.2226 | 0.4965 | 0.106* | |
H11E | 0.9206 | −0.2635 | 0.5811 | 0.106* | |
H11F | 0.9198 | −0.1362 | 0.5612 | 0.106* | |
C12 | 0.7256 (3) | −0.24421 (18) | 0.49148 (14) | 0.0591 (5) | |
C13 | 0.5790 (3) | −0.1993 (2) | 0.52928 (18) | 0.0753 (6) | |
H13 | 0.5438 | −0.1241 | 0.5397 | 0.090* | |
C14 | 0.4834 (4) | −0.2660 (3) | 0.5520 (2) | 0.0967 (9) | |
H14 | 0.3839 | −0.2360 | 0.5775 | 0.116* | |
C15 | 0.5371 (5) | −0.3757 (3) | 0.5364 (2) | 0.1063 (11) | |
H15 | 0.4732 | −0.4205 | 0.5510 | 0.128* | |
C16 | 0.6833 (5) | −0.4217 (3) | 0.4998 (2) | 0.1086 (11) | |
H16 | 0.7183 | −0.4973 | 0.4906 | 0.130* | |
C17 | 0.7792 (4) | −0.3553 (2) | 0.47636 (19) | 0.0831 (7) | |
H17 | 0.8785 | −0.3856 | 0.4507 | 0.100* | |
N1 | 0.70532 (18) | 0.00886 (13) | 0.26945 (11) | 0.0508 (4) | |
N2 | 0.7257 (2) | −0.08131 (15) | 0.33979 (13) | 0.0587 (5) | |
O1 | 0.72154 (17) | 0.21260 (13) | 0.19595 (10) | 0.0583 (4) | |
O2 | 0.6966 (2) | 0.37270 (13) | 0.05338 (12) | 0.0787 (5) | |
S1 | 0.90153 (6) | 0.01123 (5) | 0.38868 (4) | 0.06229 (17) | |
H2 | 0.696 (2) | −0.1333 (19) | 0.3390 (15) | 0.055 (6)* | |
H2' | 0.852 (2) | 0.3591 (18) | 0.1810 (15) | 0.053 (6)* | |
H1 | 0.734 (3) | 0.151 (2) | 0.2363 (18) | 0.074 (8)* | |
H1' | 0.721 (3) | 0.646 (2) | 0.2595 (18) | 0.080 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1' | 0.0439 (9) | 0.0485 (10) | 0.0425 (9) | −0.0191 (8) | −0.0086 (7) | −0.0034 (8) |
C2' | 0.0498 (10) | 0.0491 (10) | 0.0491 (10) | −0.0173 (8) | −0.0059 (8) | −0.0082 (8) |
C3' | 0.0463 (10) | 0.0629 (13) | 0.0674 (13) | −0.0134 (9) | −0.0037 (9) | −0.0127 (10) |
C4' | 0.0432 (10) | 0.0735 (14) | 0.0822 (15) | −0.0233 (10) | −0.0069 (10) | −0.0155 (12) |
C5' | 0.0525 (11) | 0.0580 (12) | 0.0698 (13) | −0.0256 (9) | −0.0100 (9) | −0.0132 (10) |
C6' | 0.0442 (9) | 0.0475 (10) | 0.0466 (10) | −0.0171 (8) | −0.0091 (7) | −0.0057 (8) |
C7' | 0.0737 (16) | 0.0634 (15) | 0.127 (2) | −0.0094 (12) | −0.0116 (15) | −0.0429 (16) |
C8' | 0.0524 (11) | 0.0481 (11) | 0.0612 (12) | −0.0190 (8) | −0.0109 (9) | −0.0117 (9) |
C9' | 0.0487 (10) | 0.0529 (11) | 0.0721 (13) | −0.0172 (9) | −0.0114 (9) | −0.0053 (10) |
N3' | 0.0459 (9) | 0.0640 (12) | 0.1040 (15) | −0.0094 (8) | −0.0122 (9) | −0.0202 (11) |
C11' | 0.0482 (12) | 0.0846 (18) | 0.121 (2) | −0.0086 (12) | −0.0211 (13) | 0.0003 (16) |
C12' | 0.0456 (11) | 0.0557 (13) | 0.104 (2) | −0.0131 (9) | 0.0044 (11) | −0.0232 (13) |
C13' | 0.098 (2) | 0.092 (2) | 0.112 (3) | −0.0441 (17) | 0.0020 (18) | −0.0316 (19) |
C14' | 0.115 (3) | 0.180 (4) | 0.115 (3) | −0.066 (3) | 0.023 (2) | −0.068 (3) |
C15' | 0.127 (3) | 0.165 (5) | 0.223 (6) | −0.067 (4) | 0.045 (4) | −0.138 (5) |
C16' | 0.140 (4) | 0.096 (3) | 0.254 (6) | −0.060 (3) | 0.012 (4) | −0.074 (4) |
C17' | 0.091 (2) | 0.0644 (17) | 0.162 (3) | −0.0304 (15) | −0.004 (2) | −0.0195 (19) |
N1' | 0.0465 (9) | 0.0501 (9) | 0.0722 (11) | −0.0117 (7) | −0.0096 (8) | −0.0177 (8) |
N2' | 0.0476 (9) | 0.0545 (11) | 0.0977 (15) | −0.0111 (8) | −0.0134 (9) | −0.0313 (10) |
O1' | 0.0447 (7) | 0.0542 (9) | 0.0810 (10) | −0.0192 (7) | −0.0095 (7) | −0.0199 (8) |
O2' | 0.0575 (8) | 0.0539 (8) | 0.0921 (11) | −0.0178 (7) | −0.0036 (7) | −0.0287 (8) |
S1' | 0.0668 (4) | 0.0854 (4) | 0.0921 (5) | −0.0325 (3) | −0.0188 (3) | −0.0231 (4) |
C1 | 0.0426 (9) | 0.0468 (10) | 0.0481 (10) | −0.0140 (8) | −0.0082 (7) | −0.0071 (8) |
C2 | 0.0596 (12) | 0.0509 (11) | 0.0590 (12) | −0.0197 (9) | −0.0097 (9) | 0.0019 (9) |
C3 | 0.1032 (19) | 0.0799 (17) | 0.0563 (13) | −0.0331 (15) | −0.0295 (13) | 0.0157 (12) |
C4 | 0.153 (3) | 0.093 (2) | 0.0704 (16) | −0.054 (2) | −0.0632 (18) | 0.0097 (15) |
C5 | 0.124 (2) | 0.0737 (15) | 0.0705 (15) | −0.0495 (15) | −0.0499 (15) | 0.0029 (12) |
C6 | 0.0561 (10) | 0.0491 (10) | 0.0487 (10) | −0.0187 (8) | −0.0170 (8) | −0.0051 (8) |
C7 | 0.134 (3) | 0.085 (2) | 0.113 (2) | −0.064 (2) | −0.033 (2) | 0.0385 (18) |
C8 | 0.0627 (12) | 0.0490 (11) | 0.0581 (12) | −0.0254 (9) | −0.0186 (9) | −0.0058 (9) |
C9 | 0.0495 (10) | 0.0510 (11) | 0.0487 (10) | −0.0139 (8) | −0.0130 (8) | −0.0062 (8) |
N3 | 0.0698 (11) | 0.0592 (10) | 0.0550 (10) | −0.0263 (9) | −0.0256 (8) | 0.0056 (8) |
C11 | 0.0703 (14) | 0.0764 (15) | 0.0650 (14) | −0.0174 (12) | −0.0310 (11) | 0.0032 (12) |
C12 | 0.0838 (15) | 0.0537 (12) | 0.0465 (11) | −0.0282 (11) | −0.0224 (10) | 0.0035 (9) |
C13 | 0.0834 (17) | 0.0713 (15) | 0.0777 (16) | −0.0339 (13) | −0.0150 (13) | −0.0054 (13) |
C14 | 0.103 (2) | 0.116 (3) | 0.0865 (19) | −0.064 (2) | −0.0128 (16) | −0.0007 (18) |
C15 | 0.157 (3) | 0.108 (3) | 0.085 (2) | −0.091 (3) | −0.031 (2) | 0.0150 (19) |
C16 | 0.181 (4) | 0.0621 (17) | 0.103 (2) | −0.056 (2) | −0.044 (3) | −0.0020 (16) |
C17 | 0.112 (2) | 0.0597 (14) | 0.0803 (17) | −0.0263 (14) | −0.0239 (15) | −0.0062 (13) |
N1 | 0.0610 (9) | 0.0469 (9) | 0.0518 (9) | −0.0244 (7) | −0.0209 (7) | 0.0028 (7) |
N2 | 0.0782 (12) | 0.0510 (10) | 0.0617 (11) | −0.0349 (9) | −0.0330 (9) | 0.0086 (8) |
O1 | 0.0783 (10) | 0.0512 (8) | 0.0576 (8) | −0.0312 (7) | −0.0233 (7) | −0.0019 (7) |
O2 | 0.1046 (13) | 0.0593 (9) | 0.0791 (11) | −0.0429 (9) | −0.0219 (9) | 0.0115 (8) |
S1 | 0.0601 (3) | 0.0662 (3) | 0.0720 (4) | −0.0300 (3) | −0.0214 (3) | −0.0055 (3) |
C1'—O1' | 1.356 (2) | C1—O1 | 1.351 (2) |
C1'—C6' | 1.396 (3) | C1—C2 | 1.389 (3) |
C1'—C2' | 1.397 (3) | C1—C6 | 1.397 (3) |
C2'—O2' | 1.369 (2) | C2—O2 | 1.367 (3) |
C2'—C3' | 1.379 (3) | C2—C3 | 1.374 (3) |
C3'—C4' | 1.382 (3) | C3—C4 | 1.375 (4) |
C3'—H3' | 0.9300 | C3—H3 | 0.9300 |
C4'—C5' | 1.365 (3) | C4—C5 | 1.360 (3) |
C4'—H4' | 0.9300 | C4—H4 | 0.9300 |
C5'—C6' | 1.402 (3) | C5—C6 | 1.391 (3) |
C5'—H5' | 0.9300 | C5—H5 | 0.9300 |
C6'—C8' | 1.454 (3) | C6—C8 | 1.444 (3) |
C7'—O2' | 1.413 (3) | C7—O2 | 1.426 (3) |
C7'—H7'1 | 0.9600 | C7—H7A | 0.9600 |
C7'—H7'2 | 0.9600 | C7—H7B | 0.9600 |
C7'—H7'3 | 0.9600 | C7—H7C | 0.9600 |
C8'—N1' | 1.270 (2) | C8—N1 | 1.268 (2) |
C8'—H8' | 0.9300 | C8—H8 | 0.9300 |
C9'—N3' | 1.347 (3) | C9—N3 | 1.352 (2) |
C9'—N2' | 1.364 (3) | C9—N2 | 1.361 (2) |
C9'—S1' | 1.657 (2) | C9—S1 | 1.666 (2) |
N3'—C12' | 1.431 (3) | N3—C12 | 1.441 (3) |
N3'—C11' | 1.466 (3) | N3—C11 | 1.463 (3) |
C11'—H11A | 0.9600 | C11—H11D | 0.9600 |
C11'—H11B | 0.9600 | C11—H11E | 0.9600 |
C11'—H11C | 0.9600 | C11—H11F | 0.9600 |
C12'—C17' | 1.366 (4) | C12—C17 | 1.372 (3) |
C12'—C13' | 1.375 (4) | C12—C13 | 1.373 (3) |
C13'—C14' | 1.382 (5) | C13—C14 | 1.388 (4) |
C13'—H13' | 0.9300 | C13—H13 | 0.9300 |
C14'—C15' | 1.363 (6) | C14—C15 | 1.358 (5) |
C14'—H14' | 0.9300 | C14—H14 | 0.9300 |
C15'—C16' | 1.348 (7) | C15—C16 | 1.368 (5) |
C15'—H15' | 0.9300 | C15—H15 | 0.9300 |
C16'—C17' | 1.389 (6) | C16—C17 | 1.386 (4) |
C16'—H16' | 0.9300 | C16—H16 | 0.9300 |
C17'—H17' | 0.9300 | C17—H17 | 0.9300 |
N1'—N2' | 1.372 (2) | N1—N2 | 1.364 (2) |
N2'—H2' | 0.83 (2) | N2—H2 | 0.80 (2) |
O1'—H1' | 0.79 (3) | O1—H1 | 0.87 (3) |
O1'—C1'—C6' | 123.80 (17) | O1—C1—C2 | 117.42 (17) |
O1'—C1'—C2' | 116.83 (16) | O1—C1—C6 | 123.16 (17) |
C6'—C1'—C2' | 119.37 (16) | C2—C1—C6 | 119.40 (17) |
O2'—C2'—C3' | 125.16 (18) | O2—C2—C3 | 124.7 (2) |
O2'—C2'—C1' | 114.36 (16) | O2—C2—C1 | 114.85 (18) |
C3'—C2'—C1' | 120.48 (18) | C3—C2—C1 | 120.4 (2) |
C2'—C3'—C4' | 119.92 (19) | C2—C3—C4 | 120.2 (2) |
C2'—C3'—H3' | 120.0 | C2—C3—H3 | 119.9 |
C4'—C3'—H3' | 120.0 | C4—C3—H3 | 119.9 |
C5'—C4'—C3' | 120.50 (19) | C5—C4—C3 | 119.9 (2) |
C5'—C4'—H4' | 119.7 | C5—C4—H4 | 120.0 |
C3'—C4'—H4' | 119.7 | C3—C4—H4 | 120.0 |
C4'—C5'—C6' | 120.62 (19) | C4—C5—C6 | 121.4 (2) |
C4'—C5'—H5' | 119.7 | C4—C5—H5 | 119.3 |
C6'—C5'—H5' | 119.7 | C6—C5—H5 | 119.3 |
C1'—C6'—C5' | 119.10 (17) | C5—C6—C1 | 118.64 (18) |
C1'—C6'—C8' | 121.69 (16) | C5—C6—C8 | 119.08 (18) |
C5'—C6'—C8' | 119.21 (17) | C1—C6—C8 | 122.27 (16) |
O2'—C7'—H7'1 | 109.5 | O2—C7—H7A | 109.5 |
O2'—C7'—H7'2 | 109.5 | O2—C7—H7B | 109.5 |
H7'1—C7'—H7'2 | 109.5 | H7A—C7—H7B | 109.5 |
O2'—C7'—H7'3 | 109.5 | O2—C7—H7C | 109.5 |
H7'1—C7'—H7'3 | 109.5 | H7A—C7—H7C | 109.5 |
H7'2—C7'—H7'3 | 109.5 | H7B—C7—H7C | 109.5 |
N1'—C8'—C6' | 119.62 (18) | N1—C8—C6 | 119.82 (17) |
N1'—C8'—H8' | 120.2 | N1—C8—H8 | 120.1 |
C6'—C8'—H8' | 120.2 | C6—C8—H8 | 120.1 |
N3'—C9'—N2' | 114.31 (19) | N3—C9—N2 | 114.93 (17) |
N3'—C9'—S1' | 123.28 (16) | N3—C9—S1 | 123.36 (14) |
N2'—C9'—S1' | 122.41 (16) | N2—C9—S1 | 121.71 (15) |
C9'—N3'—C12' | 122.44 (18) | C9—N3—C12 | 121.84 (16) |
C9'—N3'—C11' | 120.9 (2) | C9—N3—C11 | 120.89 (18) |
C12'—N3'—C11' | 116.4 (2) | C12—N3—C11 | 117.18 (17) |
N3'—C11'—H11A | 109.5 | N3—C11—H11D | 109.5 |
N3'—C11'—H11B | 109.5 | N3—C11—H11E | 109.5 |
H11A—C11'—H11B | 109.5 | H11D—C11—H11E | 109.5 |
N3'—C11'—H11C | 109.5 | N3—C11—H11F | 109.5 |
H11A—C11'—H11C | 109.5 | H11D—C11—H11F | 109.5 |
H11B—C11'—H11C | 109.5 | H11E—C11—H11F | 109.5 |
C17'—C12'—C13' | 119.9 (3) | C17—C12—C13 | 120.5 (2) |
C17'—C12'—N3' | 120.2 (3) | C17—C12—N3 | 119.8 (2) |
C13'—C12'—N3' | 119.9 (2) | C13—C12—N3 | 119.7 (2) |
C12'—C13'—C14' | 121.2 (3) | C12—C13—C14 | 120.1 (3) |
C12'—C13'—H13' | 119.4 | C12—C13—H13 | 120.0 |
C14'—C13'—H13' | 119.4 | C14—C13—H13 | 120.0 |
C15'—C14'—C13' | 118.1 (5) | C15—C14—C13 | 119.0 (3) |
C15'—C14'—H14' | 121.0 | C15—C14—H14 | 120.5 |
C13'—C14'—H14' | 121.0 | C13—C14—H14 | 120.5 |
C16'—C15'—C14' | 121.5 (5) | C14—C15—C16 | 121.4 (3) |
C16'—C15'—H15' | 119.3 | C14—C15—H15 | 119.3 |
C14'—C15'—H15' | 119.3 | C16—C15—H15 | 119.3 |
C15'—C16'—C17' | 120.7 (4) | C15—C16—C17 | 119.9 (3) |
C15'—C16'—H16' | 119.6 | C15—C16—H16 | 120.1 |
C17'—C16'—H16' | 119.6 | C17—C16—H16 | 120.1 |
C12'—C17'—C16' | 118.7 (4) | C12—C17—C16 | 119.1 (3) |
C12'—C17'—H17' | 120.7 | C12—C17—H17 | 120.4 |
C16'—C17'—H17' | 120.7 | C16—C17—H17 | 120.4 |
C8'—N1'—N2' | 118.72 (17) | C8—N1—N2 | 119.19 (16) |
C9'—N2'—N1' | 118.18 (18) | C9—N2—N1 | 117.98 (17) |
C9'—N2'—H2' | 123.2 (15) | C9—N2—H2 | 122.1 (15) |
N1'—N2'—H2' | 117.9 (15) | N1—N2—H2 | 119.2 (15) |
C1'—O1'—H1' | 106 (2) | C1—O1—H1 | 108.0 (17) |
C2'—O2'—C7' | 117.91 (17) | C2—O2—C7 | 117.5 (2) |
O1'—C1'—C2'—O2' | −0.4 (2) | O1—C1—C2—O2 | −0.3 (3) |
C6'—C1'—C2'—O2' | 179.33 (16) | C6—C1—C2—O2 | −178.80 (18) |
O1'—C1'—C2'—C3' | 179.63 (18) | O1—C1—C2—C3 | 180.0 (2) |
C6'—C1'—C2'—C3' | −0.6 (3) | C6—C1—C2—C3 | 1.5 (3) |
O2'—C2'—C3'—C4' | −179.5 (2) | O2—C2—C3—C4 | −179.7 (3) |
C1'—C2'—C3'—C4' | 0.4 (3) | C1—C2—C3—C4 | 0.0 (4) |
C2'—C3'—C4'—C5' | 0.4 (3) | C2—C3—C4—C5 | −0.9 (5) |
C3'—C4'—C5'—C6' | −1.0 (3) | C3—C4—C5—C6 | 0.3 (5) |
O1'—C1'—C6'—C5' | 179.77 (18) | C4—C5—C6—C1 | 1.1 (4) |
C2'—C1'—C6'—C5' | 0.0 (3) | C4—C5—C6—C8 | −177.6 (3) |
O1'—C1'—C6'—C8' | −0.2 (3) | O1—C1—C6—C5 | 179.6 (2) |
C2'—C1'—C6'—C8' | −179.90 (17) | C2—C1—C6—C5 | −2.0 (3) |
C4'—C5'—C6'—C1' | 0.8 (3) | O1—C1—C6—C8 | −1.8 (3) |
C4'—C5'—C6'—C8' | −179.30 (19) | C2—C1—C6—C8 | 176.68 (18) |
C1'—C6'—C8'—N1' | 0.9 (3) | C5—C6—C8—N1 | 179.5 (2) |
C5'—C6'—C8'—N1' | −179.04 (19) | C1—C6—C8—N1 | 0.8 (3) |
N2'—C9'—N3'—C12' | 13.4 (3) | N2—C9—N3—C12 | −13.3 (3) |
S1'—C9'—N3'—C12' | −166.54 (19) | S1—C9—N3—C12 | 166.72 (16) |
N2'—C9'—N3'—C11' | −173.3 (2) | N2—C9—N3—C11 | 170.3 (2) |
S1'—C9'—N3'—C11' | 6.7 (3) | S1—C9—N3—C11 | −9.7 (3) |
C9'—N3'—C12'—C17' | −104.5 (3) | C9—N3—C12—C17 | 113.3 (2) |
C11'—N3'—C12'—C17' | 81.9 (3) | C11—N3—C12—C17 | −70.2 (3) |
C9'—N3'—C12'—C13' | 76.3 (3) | C9—N3—C12—C13 | −69.1 (3) |
C11'—N3'—C12'—C13' | −97.2 (3) | C11—N3—C12—C13 | 107.5 (2) |
C17'—C12'—C13'—C14' | −1.1 (4) | C17—C12—C13—C14 | −0.4 (4) |
N3'—C12'—C13'—C14' | 178.1 (3) | N3—C12—C13—C14 | −178.0 (2) |
C12'—C13'—C14'—C15' | −0.3 (5) | C12—C13—C14—C15 | 0.1 (4) |
C13'—C14'—C15'—C16' | 1.8 (7) | C13—C14—C15—C16 | 0.6 (5) |
C14'—C15'—C16'—C17' | −1.9 (8) | C14—C15—C16—C17 | −1.0 (5) |
C13'—C12'—C17'—C16' | 1.0 (5) | C13—C12—C17—C16 | 0.0 (4) |
N3'—C12'—C17'—C16' | −178.1 (3) | N3—C12—C17—C16 | 177.6 (2) |
C15'—C16'—C17'—C12' | 0.4 (7) | C15—C16—C17—C12 | 0.7 (4) |
C6'—C8'—N1'—N2' | −178.57 (18) | C6—C8—N1—N2 | −178.81 (18) |
N3'—C9'—N2'—N1' | −173.90 (19) | N3—C9—N2—N1 | 177.54 (17) |
S1'—C9'—N2'—N1' | 6.0 (3) | S1—C9—N2—N1 | −2.4 (3) |
C8'—N1'—N2'—C9' | −162.8 (2) | C8—N1—N2—C9 | 161.71 (19) |
C3'—C2'—O2'—C7' | 4.8 (3) | C3—C2—O2—C7 | −11.3 (4) |
C1'—C2'—O2'—C7' | −175.1 (2) | C1—C2—O2—C7 | 169.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.87 (2) | 1.85 (3) | 2.611 (2) | 146 (3) |
O1′—H1′···N1′ | 0.80 (3) | 1.89 (2) | 2.609 (2) | 149 (3) |
N2—H2···O1′i | 0.80 (2) | 2.59 (2) | 3.341 (2) | 157 (2) |
N2—H2···O2′i | 0.80 (2) | 2.52 (2) | 3.081 (3) | 128 (2) |
N2′—H2′···O1 | 0.83 (2) | 2.51 (2) | 3.282 (3) | 156.1 (19) |
N2′—H2′···O2 | 0.83 (2) | 2.62 (2) | 3.214 (3) | 130.0 (19) |
C8—H8···O2′i | 0.93 | 2.52 | 3.085 (3) | 120 |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.87 (2) | 1.85 (3) | 2.611 (2) | 146 (3) |
O1'—H1'···N1' | 0.80 (3) | 1.89 (2) | 2.609 (2) | 149 (3) |
N2—H2···O1'i | 0.80 (2) | 2.59 (2) | 3.341 (2) | 157 (2) |
N2—H2···O2'i | 0.80 (2) | 2.52 (2) | 3.081 (3) | 128 (2) |
N2'—H2'···O1 | 0.83 (2) | 2.51 (2) | 3.282 (3) | 156.1 (19) |
N2'—H2'···O2 | 0.83 (2) | 2.62 (2) | 3.214 (3) | 130.0 (19) |
C8—H8···O2'i | 0.93 | 2.52 | 3.085 (3) | 120 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H17N3O2S |
Mr | 315.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.6869 (2), 12.6140 (2), 14.7498 (3) |
α, β, γ (°) | 77.839 (1), 76.5330 (9), 70.875 (1) |
V (Å3) | 1638.19 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.931, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24246, 6781, 5047 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.139, 1.05 |
No. of reflections | 6781 |
No. of parameters | 417 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.30 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors thank Professor Babu Varghese and Dr Jagan, SAIF, IIT Madras, Chennai, India, for the
data collection.References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., Garc\?ía-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197–261. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gangadharan, R., Haribabu, J., Karvembu, R. & Sethusankar, K. (2014). Acta Cryst. E70, o1039–o1040. CSD CrossRef IUCr Journals Google Scholar
Gangadharan, R., Haribabu, J., Karvembu, R. & Sethusankar, K. (2015). Acta Cryst. E71, 305–308. Web of Science CSD CrossRef IUCr Journals Google Scholar
Greenbaum, D. C., Mackey, Z., Hansell, E., Doyle, P., Gut, J., Caffrey, C. R., Lehrman, J., Rosenthal, P. J., McKerrow, J. H. & Chibale, K. (2004). J. Med. Chem. 47, 3212–3219. Web of Science CrossRef PubMed CAS Google Scholar
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CSD CrossRef CAS Google Scholar
Küçükgüzel, G., Kocatepe, A., De Clercq, E., Şahin, F. & Güllüce, M. (2006). Eur. J. Med. Chem. 41, 353–359. PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Philip, V., Suni, V. & Kurup, M. R. P. (2004). Acta Cryst. C60, o856–o858. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Quiroga, A. G., Pérez, J. M., López-Solera, I., Masaguer, J. R., Luque, A., Román, P., Edwards, A., Alonso, C. & Navarro-Ranninger, C. (1998). J. Med. Chem. 41, 1399–1408. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rapheal, P. F., Manoj, E., Kurup, M. R. P. & Suresh, E. (2007). Polyhedron, 26, 607–616. Web of Science CSD CrossRef CAS Google Scholar
Seena, E. B., Kurup, M. R. P. & Suresh, E. (2008). J. Chem. Crystallogr. 38, 93–96. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreekanth, A., Fun, H.-K. & Kurup, M. R. P. (2004). Inorg. Chem. Commun. 7, 1250–1253. Web of Science CSD CrossRef CAS Google Scholar
Tenório, R. P., Góes, A. J. S., de Lima, J. G., de Faria, A. R., Alves, A. J. & de Aquino, T. M. (2005). Quím. Nova, 28, 1030–1037. Google Scholar
Tian, Y.-P., Duan, C.-Y., Zhao, C.-Y. & You, X.-Z. (1997). Inorg. Chem. 36, 1247–1252. CSD CrossRef PubMed CAS Web of Science Google Scholar
Vimala, G., Govindaraj, J., Haribabu, J., Karvembu, R. & SubbiahPandi, A. (2014). Acta Cryst. E70, o1151. CSD CrossRef IUCr Journals Google Scholar
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